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Art on theMart Nutcracker projection
Photograph: Courtesy Art on theMART, Original production photography by Cheryl Mann

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Zach Long
Written by
Zach Long
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If the Christmas light displays and holiday pop-up bars haven't tipped you off, Christmas in Chicago is on it's way—and the first weekend of December offers plenty of ways to prepare. Shop for gifts at a variety of holiday markets, including the One of a Kind show at Merchandise Mart or the Andersonville Winter Market. If you're looking for entertainment, you can keep it seasonal by catching a Christmas-themed Cirque du Soleil at the Chicago Theatre, or join Ohmme and Alex Grelle for a celebration of the work of singer-songwriter Kate Bush. Plus, there's a Princess Diana exhibition and new projections to see during Art on theMart. Kick off the most festive time of year with some of the best things to do in Chicago this weekend.

RECOMMENDED: The best things to do in Chicago right now

Things to do this weekend in Chicago

  • Things to do
  • Markets and fairs
  • Loop

After going virtual in 2020, the iconic German-inspired holiday market at Daley Plaza returns to Chicago this year for just over a month of Christmassy celebrations. Details about specific vendors are still relatively light at the moment, but you can expect stalls stocked with handmade gifts, German food and plenty of hot beverages (including spiced glühwein, though jury's out on whether we'll get to sip from one of the market's famous boot mugs). Similarly, you can expect to see more information about COVID-19 safety protocols in the coming weeks, though organizers have announced that they'll bring back a virtual component to the market. We'll keep you posted about updates, but in the meantime, we're counting down the days until this holiday tradition returns. 

  • Art
  • Film and video

Projecting a 25-story-tall video installation on the side of the Merchandise Mart, Art on theMart's holiday program includes works by Chicago teens, stills from the Joffrey Ballet's production of The Nutcracker and an AI-generated display from Ouchhh Studios. Take in a series of mosaics created by kids in Chicago's After School Matters before experiencing images from The Nutcracker set to Tchaikovsky’s beloved score and the Harmonic AI animations, inspired by some of Chicago's best jazz musicians.

Art on theMART's array of 34 digital projectors display the 30-minute program at 7:30 and 8pm every evening. The show is best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

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  • Shopping
  • Streeterville

For the past two years, Randolph Street Market—the European-style market where vendors hawk antique housewares, furniture, ephemera, clothing and more treasures—has been on a pandemic-induced hiatus in Chicago. This December, the market returns in a new location for a limited-run, three-weekend pop-up just in time for the holiday season. 

Instead of its usual Randolph Street-adjacent location in Plumbers Hall (or Three Oaks, Michigan, where the market moved this summer), the December pop-up will operate out of the ground floor of the massive space that once housed Topshop at 830 N Michigan Avenue. More than 75 vendors, including Maison Parisienne, This Old Book, Violet and Suds, Atlantic Poster and more, will be on hand—stop in to find the perfect unique gift for everyone on your list, whether they're into vintage costume jewelry, rare novels, art prints, handmade bath bombs or something else entirely. 

  • Music
  • Rock and indie
  • North Center

The music of English singer-songwriter Kate Bush (best known for singles like "Wuthering Heights" and "Running Up That Hill") is adapted for the stage in this new show, featuring Macie Stewart and Sima Cunningham of local art-rock duo Ohmme, as well as performer Alex Grelle. With shows scheduled at Constellation and Co-Prosperity Sphere, Full Bush includes live music (from a six-piece lineup of Ohmme), choreographed dancing and projections that explore the iconography of Bush's career—plus, plenty of costume changes.

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  • Time Out Market
  • West Loop

Embrace the spirit(s) of the season while enjoying festive tropical cocktails at Secret Sand-ta, the holiday-inspired cocktail bar inside of Time Out Market Chicago. Featuring drinks from expert mixologist Paul McGee (Lost Lake, Milk Room), this speakeasy-style pop-up operates out of window on the second floor of Time Out Market Chicago. Just head upstairs and look for the festive decorations, then hop in line to order a Hot Buttered Rhum Cider, a North Pole Nog or another drink festooned with jolly garnishes. Secret Sand-ta opens at 5pm on Fridays and Saturdays. 

  • Art
  • Photography
  • Suburbs

More than 20 years after her untimely death, Princess Diana has once again entered the realm of public obsession thanks to new media like Netflix's The Crown, a Broadway show called Diana: The Musical and the upcoming movie Spencer starring Kristen Stewart. Chicago fans will have yet another way to learn about the life of the iconic princess starting this December, when a traveling exhibition of images and stories chronicling Diana's life lands at the suburban Oakbrook Center mall. 

"Princess Diana Exhibition: Accredited Access" showcases photographs from royal photographer Anwar Hussein and his two sons, Zak and Samir—who collectively spent more than four decades photographing Diana and her family—alongside art, murals, artifacts and rarely-told stories from the Hussein family that provide behind-the-scenes context to the photos. The exhibition is broken up into eight themed sections with topics ranging from "glam" to "unguarded," aiming to capture a comprehensive look at Diana's life. Along the way, art installations from multimedia artist Pauline Loctin depict interpretations of Diana's most famous moments. And of course, at the end of the tour, visitors can stop by the exhibition store to grab Diana-themed merch. 

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  • Things to do
  • Late openings
  • Lincoln Park

To see one of the largest displays of holiday lights within city limits, you need to head to Lincoln Park Zoo, where the annual ZooLights display strings up millions of LED blubs. While most of the animals will be keeping warm inside, visitors are free to wander through the park, snapping photos of the various displays and taking part in a variety of activities throughout the holiday season.

There a some new features to look forward to this season, including a new light show on the South Lawn and a 18-foot holiday tree outside the newly-renovated Pepper Family Wildlife Center, where red pandas and snow leopards can be found. Guests will also be able to enjoy hot beverages and snacks at stands throughout the park.

Just like last year, a $5 admission fee will be charged throughout most of the week—free admission tickets will be offered on Mondays and Tuesdays. Check out the Lincoln Park Zoo website for information on special ticketed events during ZooLights, including the BrewLights beer festival and a musical tribute to “A Charlie Brown Christmas.”

  • Theater
  • Musicals
  • Loop

Disney's latest Broadway adaptation comes to Chicago, bringing the smash-hit animated movie Frozen to life in front of your eyes. Adapting the contemporary fairy tale about a princess with frigid magical powers, the stage version comes complete with all the songs you (and any kids you know) are already familiar with, including the inescapable earworm, "Let It Go." Settle in for powerful anthems, spectacular special effects and strange human-manipulated versions of Olaf the snowman and Sven the reindeer.

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  • Nightlife
  • Pop-ups and food events
  • River North

Frosty's Christmas Bar in Goose Island brings three levels of festive fun, four bars, two dance floors, life-size toy soldiers and a themed soundtrack that keeps the crowd bumping until 4am every night of the week. Don your favorite holiday attire and enjoy a glass of something boozy and marshmallow-topped while eating Christmas cookies amid the twinkling lights, tinsel and over-the-top decorations; plus, keep an eye out for a singing Santa and dancing elves. 

  • Things to do
  • Ice skating
  • Millennium Park

Situated in the heart of downtown Chicago, with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that's twice the length of a lap around a traditional rink. This year's edition of the ribbon will be decorated with designs inspired by Vincent van Gogh's "Sunflowers" and "Starry Night" paintings, a collaboration between the art exhibition "Immersive Van Gogh" and Chicago Park District. 

Admission to the Skating Ribbon is free during weekdays if you bring your own skates; otherwise, reservations are $5 (with skates on weekends on holidays) or $16–$20 if you need to rent a pair. The Ribbon stays open through March (weather permitting) and even offers limited hours on Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

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  • Things to do
  • Millennium Park

Every year, Millennium Park is adorned with an epic Christmas tree that remains on display until the beginning of the new year. The larger-than-life attraction is festooned with twinkling lights and crowned with an illuminated star. Spectators can check out the festive tree near Washington Street and Michigan Avenue through Sunday, January 9th.

The annual Christmas Tree Lighting Ceremony will return in-person this year on Friday, November 19 starting at 6pm, featuring special guests and performances ahead of the illumination of the 108th Chicago Christmas Tree.

  • Things to do
  • Festivals
  • Streeterville

Too cold outside? Navy Pier brings all of the winter fun indoors, filling its gigantic 170,000-square-foot Festival Hall with a regulation-size Alpine ice skating rink, a holiday beer garden, kiddie train rides, Santa’s Village and a gift market. The centerpiece of Light Up the Lake (which replaces Navy Pier's Winter Wonderfest) is a collection of oversized light sculptures, including a giant Teddy Bear, 25-foot-tall deer, a 60-foot light tunnel and 40-foot tree. Boasting more than 600,000 lights, Navy Pier claims that it's "the area's largest indoor lights show." Plus, each Light Up the Lake ticket includes a ride on Navy Pier's 200-foot Centennial Wheel—don't worry, all of the gondolas are fully enclosed and heated!

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  • Art
  • Digital & interactive
  • Streeterville

Montreal-based media art studio Iregular brings an interactive art installation to Navy Pier this winter, using gigantic projections to draw attention to climate change and the global impact of our individual actions. The projections take over surfaces on Fifth Third Bank Family Pavilion, near the fountain at Polk Bros Park, in Pier Park near the Centennial Wheel and on the South Dock near Billy Goat Tavern.

You won't just be watching the projections—the digital displays respond to movement and the light on your cellphone, creating shifting geometric patterns and causing new images to appear. Each projection corresponds to a different environmental aspect, including wildlife, waste and icebergs.

"Our Common Home" will run in tandem with all of the other attractions that Navy Pier has to offer, so you can visit the Light Up the Lake experience or ride the Centennial Wheel while you're there.

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  • Time Out Market
  • West Loop

On Friday nights, the DJ Firm brings some of Chicago's top DJs to Time Out Market Chicago to spin tunes for guests. Enjoy a drink from the Time Out Market Bar or some delicious dishes from one of the food hall's meny vendors while you listen (or dance) to the music. This week, DJ Louie Cue spins some tunes.

  • Theater
  • Lincoln Park

Steppenwolf Theatre's revival of Tracy Letts' comedy-thriller was interrupted by the pandemic, but the drastic changes and periods of isolation that so many of us experienced over the past two years have only heighted the effectiveness of Bug. Picking up where they left off when the play's run was cut off last March, Carrie Coon and Namir Smallwood portray a couple who have holed up in an Oklahoma motel room. Paranoia and suspicion set in as the pair fights off an insect infestation that seemingly only they can perceive. It's a small, intimate story that builds up to a terrifying crescendo—prepare yourself for the white-knuckled second act.

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  • Bars
  • North Center

Indulge in a little childhood nostalgia at this pop-up bar that pays homage to Rudolph the Red-Nosed Reindeer & the Island of Misfit Toys. Hosted by The Rambler in North Center, Misfit Christmas opens with an outdoor scene decorated by 10-foot, custom-painted wood characters from the Island of Misfit Toys; inside, every room of the bar corresponds with a different scene from the movie (like the snowy forest where Rudolph and Hermey meet and sing "We're a Couple of Misfits"), and the bar's heated and covered beer garden will turn into "Santa's workshop." Top off the experience with a festive cocktail and bites from a themed food menu. 

  • Bars
  • Avondale

Sick of the cold? Pretend you're celebrating the season somewhere tropical at Lost Lake's annual holiday party, which fills the bar with colorful tinsel, string lights and some of the city's most delightful winter cocktails. Choose from returning favorites like the Little Saint Nog (Fiji rum, spiced demerara, cream, whole egg and three types of sherry) or sample new creations like Down Through the Chimney (mezcal, sweet vermouth, amaro, cold brew, oat milk and mole bitters). Walk-ins and reservations are accepted. 

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  • Shopping
  • Markets and fairs
  • Andersonville

Shop holiday wares at this tented outdoor bazaar stocked with goods from local and Swedish vendors like Edgewater Candles, First Slice Pie Cafe, Unbind Books and more. Want to keep extra warm as you browse? Nab a cup of Simon Tavern's revered glögg to sip while you walk around. 

  • Things to do
  • Avondale

After taking a year off in 2020, Krampus—the folkloric creature that frightens children who have misbehaved throughout the year—returns to Avondale's DMen Tap for a Christmas pop-up that's more naughty than nice. The pop-up launches December 4 with a traditional Krampus parade featuring the marching band Environmental Encroachment (feel free to wear your best Krampus costume when you attend) before continuing on throughout the month with mulled wine, Revolution Brewing's Fist of Krampus holiday ale, gooey raclette sandwiches and plenty of Krampus themed events. 

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  • Theater
  • Circuses & magic
  • Loop

The crazy-athletic whimsy merchants at Cirque du Soleil bring the troupe's Christmas-themed show to the Chicago Theatre, accompanied by an international cast of dancers, acrobats and clowns. The storyline follows a jaded young girl named Isabella who finds herself in a topsy-turvy wonderland filled with characters straight out of the classic "'Twas the Night Before Christmas" poem—except they can do crazy flips and death-defying aerial stunts, too.

  • Shopping
  • Markets and fairs
  • Avondale

More than 20 vendors will pop up at Sleeping Village for this seasonal art fair, where you can browse goods—like ceramics, jewelry, prints and textiles—from Blessa Soaps, Caitlin Smith, Laila Textiles and tons of others. Note that the event is 21+ and requires proof of COVID-19 vaccination. 

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  • Things to do
  • Exhibitions
  • Suburbs

As usual, Six Flags Great America is open for the holidays, though you won't be able to ride any of its biggest roller coasters during your visit. Instead, the amusement park strings up more than three million lights for visitors to enjoy as they walk along the midways, accompanired by seasonal entertainment, photo ops, carousel rides and s'mores roasting pits.

Prefer to stay warm inside your car? Six Flags will also host a drive-through light show on select dates from December 3 through January 9, which showcases the same lights and seasonal music as you'd see and hear during the walkable experience. Tickets are available per person (not per car) and start at $17.99 a head.

  • Things to do
  • Performances
  • Millennium Park

There's nothing stopping you from showing up in front of Cloud Gate (a.k.a. "The Bean") at any point during the year and belting out your favorite holiday songs, but you can do it with a crowd of like-minded exhibitionists at this annual series of winter concerts and sing-alongs. Previously know as "Caroling at Cloud Gate," this series will be more inclusive of Chicago’s many faith backgrounds, cultures and holiday music traditions, taking place every Friday at 6pm from November 26 through December 17. Song books will be distributed at each event.

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  • Things to do
  • Lower West Side

The Chicago Latino Theater Alliance partnered with the Chicago Park District to launch this new, free series of holiday-themed performances that will pop up in city parks this November and December. The series kicks off on November 26 with "Posadas y Parranda" at Millennium Park, where Cuerdas Clásicas will perform traditional carols sung during posadas (reenactments of the biblical Mary and Joseph searching for shelter), while the Frankie Diaz Trio will perform Puerto Rican parranda music with Milly Santiago. On December 3, the series heads to the Humboldt Park Boathouse with live music, food trucks serving Latin American cuisine, and an art market. Finally, the series concludes at Pilsen's Harrison Park on December 10 with a pop-up market and performers like Mariachi Sirenas, Chicago's first all-women mariachi group. 

  • Nightlife
  • Pop-ups and food events
  • River North

Frosty's Christmas Bar in Goose Island brings three levels of festive fun, four bars, two dance floors, life-size toy soldiers and a themed soundtrack that keeps the crowd bumping until 4am every night of the week. Don your favorite holiday attire and enjoy a glass of something boozy and marshmallow-topped while eating Christmas cookies amid the twinkling lights, tinsel and over-the-top decorations; plus, keep an eye out for a singing Santa and dancing elves. 

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  • Bars
  • Café bars
  • River North

The weather outside might be frightful, but you'll be plenty cozy inside this festive heated tent pop-up at JoJo's Shake Bar. Treat yourself to over-the-top shakes—like The Winter Wonderland Shake, which is peppermint flavored and topped with cookies, marshmallows and a candy cane—fanciful seasonal cocktails and sweets like Santa's Milk & Cookie Flight, and be sure to grab a table close to the pop-up's 17-foot Christmas tree. Table reservations are $10. 

  • Theater
  • Sheffield & DePaul

The American Blues Theater has brought the humble story of George Bailey to life in various Chicago venues for the past 20 years, transforming Frank Capra's classic film into an interactive, 1940s-style radio broadcast production. After going virtual in 2020, the show returns to the live stage at the Victory Gardens Theater this year with original music, holiday carols and plenty of Christmas cheer. 

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  • Things to do
  • Festivals
  • Suburbs

More than one million lights cover the trees, fences and structures in the Brookfield Zoo at this annual holiday event, which is open for its 40th year this season. Guests can walk through a 600-foot-long tunnel featuring colored lights synchronized to music, spot larger-than-life illuminated animal sculptures and warm up with concessions such as funnel cakes, pizza, spiced wine and hot cocoa. Plus, catch new features this year like an illuminated gingerbread house and "Sea of Lights," a mile-long display of colored lights along the zoo's West Mall. 

  • Theater
  • Drama
  • Loop

The Goodman Theatre’s annual holiday production of the Charles Dickens classic returns to the stage, with Larry Yando taking on the role of Ebenezer Scrooge. The play has been a staple of the Goodman's calendar for more than 40 years, allowing returning attendees and new generations to see the quintessential Christmas story unfold before their eyes. Prepare to be visited by three spirits—and don't be suprised if A Christmas Carol's touching tale of redemption makes you shed a few tears.

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  • Bars
  • River West/West Town

Happy's expands beyond the Chicago Athletic Association for the first time this season, setting up shop in the upstairs bar at Parson's West Town with homey decor, themed slushies, TVs playing holiday movies and more cheerful fun. Keep an eye out for seasonal programming throughout the month of December, like a live performance of Vince Guaraldi's "A Charlie Brown Christmas." 

  • Theater
  • Puppet shows

When stay-at-home orders kept folks from seeing theater in-person last year, the interdisciplinary performance collective Manual Cinema crafted this fantastical (and very of-the-moment) virtual adaptation of A Christmas Carol using paper puppets, live performance and video animation set to an original score, garnering acclaim from critics at The New York Times and the Chicago Tribune. You can watch the visually arresting story—which centers around a curmudgeonly woman who stages a holiday puppet show through Zoom, to magical effect—when it returns to small screens for on-demand streaming this holiday season.

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  • Nightlife
  • Pop-ups and food events
  • Loop

Situated on the ground floor of the Chicago Athletic Association, Happy's transforms the hotel's Tank space into a holly, jolly wood-paneled dive bar serving cocktails and bar bites created by Land and Sea Dept. Admission is free and the pop-up is just a short walk from the Millennium Park ice skating rink.

  • Theater
  • Musicals
  • Loop

Premiering in Chicago ahead of its Broadway debut, Paradise Square is the latest production from Garth Drabinsky—the Canadian theater producer who restored the Nederlander Theatre, where this musical will be staged. Set in New York City in 1863 during the Civil War, the production is set in a Lower Manhattan slum, where Irish immigrants and Black Americans who escaped slavery are living together. In a saloon called Paradise Square, characters from different walks of life are thrown together, confronting their differences (and similarities) as the New York draft riots begin. Expect stirring songs about what it means to be an American and some fancy choreography from two-time Tony winner Bill T. Jones (Spring Awakening, Fela!). Harnessing the drama of American history and a diverse cast, this Broadway-bound production seems to be positioning itself as the next Hamilton.

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  • Sports and fitness

Hit the ice at the Chicago Wolves Ice Rink at Rosemont's Parkway Bank Park, where you can reserve a free 45-minute skating session every day through December (including holidays); the rink will also be open on Sundays through February. Use of the rink itself is free—with skate rentals available for $8—but you'll need a credit card to hold your reservation online. 

  • Things to do
  • Festivals
  • Wrigleyville

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's off-season. The Wrigley Field-adjacent space hosts a variety of seasonal activities, including the Wrigleyville outpost of Christkindlmarket, an ice skating rink, photos with Santa and holiday movie screenings on every Wednesday in December. Opening on November 19, you'll be able to shop for gifts, sip glühwein and enjoy delicious treats through the end of the year. Once the holidays are over, the skating rink at Winterland will stick around through February 20. Visit the Winterland website for reservations, hours and additional information about programming.

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  • Shopping
  • Markets and fairs
  • Wrigleyville

Don't feel like going to the Loop for your glühwein fix? The smaller-scale Wrigleyville outpost of Christkindlmarket returns to Gallagher Way this year with just as much holiday cheer as its downtown counterpart. Plus, Christkindlmarket Wrigleyville remains open through the end of the year, so you can extend the spirit of the season to the week after Christmas. More details about specific vendors and activities are forthcoming, so be on the lookout so you can start planning your holiday expeditions. 

  • Art
  • Old Town

Step inside of Starry Night and The Bedroom in Arles with the help of more than 50 digital projectors in this high-tech exhibition that explores the work of Vincent Van Gogh. Designed by the Italian creative team that worked on the "Atelier des Lumières" exhibitions in Paris, "Immersive Van Gogh" covers 35-foot walls with animated versions of the Dutch painters work, accompanied by a score that blends electronic and classical compositions.

The show takes up residence in the Germania Club Building in Old Town, which will go by the name Lighthouse ArtSpace Chicago and host additional interactive art exhibitions in the coming years. Occupying four rooms in the space, the "Immersive Van Gogh" presentation is around 35-minutes in length, with mostly-identical projections displayed in each of the rooms throughout the show.

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  • Things to do
  • Festivals

If you're looking for a holiday destination, Amaze Light Festival brings a twinking display, a holiday market and a tubing hill to Rosemont. Situated in Impact Field (the home of the Chicago Dogs), this seasonal attraction features light shows and seven illuminated worlds to explore, plus a variety of separately-ticketed experiences, including visits ot Santa's Workshop and Polar Peak tubing rides. Guests can also fill up on food and hot beverages before visiting a candy shop stocked with festive treats.

  • Theater
  • Lincoln Park

Previewing November 24 and opening December 5 for a limited engagement, When Harry Met Rehab is based loosely on the real-life experiences of Chicago sports radio personality, Harry Teinowitz. When Harry Met Rehab is an evening in the theater that will leave a mark that is flat-out funny, moving, and unforgettable. It is a story of redemption, perseverance, and hope. It is estimated that over 22 million Americans are in recovery. This show is for them, their families, and their friends.

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  • Things to do
  • Exhibitions
  • Hyde Park

Every year, the Museum of Science and Industry puts up its 45-foot-tall Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. This year's exhibit celebrates the golden age of travel, with themed décor and a spotlight on the Pioneer Zephyr train and the 727 in the "Take Flight" exhibit.

Visitors will be able to take in even more seasonal cheer at the accompanying "Holidays of Light" exhibit, whic recognizes the traditions of Chinese New Year, Diwali, Kwanzaa, Ramadan, Hanukkah, Visakha Puja Day and St. Lucia Day. Admission to "Christmas Around the World" and "Holidays of Light" is included with a regular Museum of Science and Industry ticket.

  • Things to do
  • Exhibitions
  • Magnificent Mile

Calling all The Office fanatics: The same team that created "The Friends Experience" is back with another nostalgic pop-culture experience that will make you feel like a Dunder Mifflin employee. Spread across two floors, the pop-up features 17 rooms that recreate sets from the show, including the Scranton Business Park workplace (which features Michael's office, Pam's reception desk and Ryan's closet) and Schrute Farms. Guests will be able to ecreate moments like Kevin's chili spill and the Dundie Awards—and you'll also find a few original props and costumes on display.

Don't forget to stop by a gift shop that's dressed up like the Warehouse, featuring merch like "World's Best Boss" mugs, sweatshirts that say "Nard Dog" and staplers (Jello not included). The gift shop will be open to both ticketed and non-ticketed guests, so even those who don't spring for the photo-friendly experience have a chance to buy some branded shirts and tchotchkes.

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  • Things to do
  • Exhibitions
  • Suburbs

The Chicago Botanic Garden hosts this annual (and quick to sell out) display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along a 1.25-mile path, the after-dark experience features a series of installations to explore, including a 110-foot tunnel made up of 100,000 lights and a group of trees festooned in bulbs that "sing" holiday songs.  

  • Theater
  • Musicals
  • Sheffield & DePaul

This musical parody of Christmassy British rom-com Love Actually had its Off-Broadway premiere in 2019, with a cast of six actors playing more than 50 of the movie's star-crossed characters; this year, it arrives in Chicago just in time for the holiday season. Catch rollicking songs like "Keira Knightley Actually" and "The Lament of Laura Linney" and ponder once and for all whether love actually is all around. 

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  • Things to do
  • Suburbs

Bring a thermos of hot chocolate and a cozy blanket to accompany your ride through Willow Hill's Winter Magic, a new drive-through holiday light experience in suburban Northbrook. Located at Willow Hill Golf Course, the display stretches over a mile of glittering lights with a bevy of cheerful themes, including "Snowflake Valley," "Reindeer Flight School" and a 250-foot animated video tunnel, among other attractions. Proceeds from the show benefit Erika's Lighthouse, a not-for-profit dedicated to fighting teenage depression. 

  • Things to do
  • Ice skating
  • Millennium Park

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Admission to the rink is free, and you can rent skates for $13–$15. Plus, take advantage of free skating lessons on most Saturdays and Sundays from 8am–9am, where you can learn both beginner- and intermediate-level skills. Note that you'll need to make a free online reservation for both regular skating and lessons this year, and if it seems too warm to skate, call ahead—this rink is open through March 6, weather permitting.

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  • Theater
  • Edgewater

In a sea of Christmas plays, a lone Hannukah production emerges: Hershel of Ostropol, the folkloric Jewish trickster, must defend the old town synagogue from goblins as Hanukkah approaches in this stage adaptation of Eric Kimmel's 1989 children's book. The show's musical touches and silliness make it perfect for kids—and best of all, both the in-person and streaming versions of the production are free to watch. 

  • Things to do
  • Festivals
  • Suburbs

A city named after nature's most stunning light show deserves an equally spectacular man-made display. The Rotary Club of Aurora organizes this holiday wonderland in Phillips Park—now in its 15th year—allowing visitors to drive through and take in a series of twinkling scenes. Last year, amid the new demand for drive-through light shows, more than 50,000 cars drove through the premises. 

Hop in the car, drive through the illuminated gate and keep an eye out for shimmering representations of Santa's toy factory, a holiday train and some giant snowflakes. You'll need to make an timed reservation ahead of your visit, but the experience is totally free—though if you're able to make a donation online, the proceeds will go to a selection of local charities.  

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  • Things to do
  • Lincoln Park

The Chicago History Museum commemorates the 150th anniversary of the Great Chicago Fire of 1871, exploring how the tragic event transpired and how it changed the city for decades to come. The family-friendly exhibition examines the details of the three-day blaze, exploring how the Irish immigrant O’Leary family was blamed for the fire and tracing the path of destruction (and 100,000 homeless residents) that the incident left in its wake. Featuring more than 100 artifacts from the museum's collection—including items that were damaged in the fire—"City on Fire: Chicago 1871" also showcases a reproduction of a cyclorama painting depicting the fire's path that was originally displayed at the World's Columbian Exposition of 1893.

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  • Bars
  • Wrigleyville

Looking for another place to celebrate the season in Wrigleyville? The creators of the popular Santa Baby Christmas Bar also run Rudolph's Christmas Bar, located just down the street at Casey Morans. Like its counterpart, the space is decked out in over-the-top, glittering decor and a near-identical menu full of holiday-themed drinks and food. 

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  • Theater
  • Musicals
  • Suburbs

In the 1942 film Holiday Inn, retired performer Jim (Bing Crosby) launches an inn that stages rollicking musical numbers every holiday, with music written by iconic composer Irving Berlin. This family-friendly adaption, performed by Drury Lane Theatre in suburban Oakbrook Terrace, takes the story and Berlin's music to the stage, including the movie's Academy Award-winning holiday classic "White Christmas" (which later went on to inspire a different holiday movie, White Christmas). 

  • Bars
  • Lake View

The 2003 holiday movie Elf takes center stage at this Wrigleyville pop-up located inside of Stretch Bar & Grill, which gets dressed up with more than 1,000 decorative elves, Christmas trees and plenty of festive Christmas lights. Take a seat at tables stocked with the four main food groups (candy, candy canes, candy corn and syrup) and treat yourself to a plate of Buddy's breakfast cereal (spaghetti loaded with maple syrup, chocolate fudge and syrup, mini marshmallows and strawberry frosted pop tarts) or a mug of build-your-own boozy hot chocolate. Want to catch a glimpse of Buddy the elf himself? Visit the pop-up between Thursday and Sunday, when he's known to make appearances from time to time. 

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  • Restaurants
  • Italian
  • River North

Love truffles? You're gonna flip for the latest pop-up restaurant at Eataly, which is serving a menu that's swimming with fresh Italian truffles and Barolo wine. Serving lunch and dinner, Il Tartufo & Barolo Bar specializes in dishes made with fresh white truffles (an Italian delicacy) and Barolo, a complex red wine made with Nebbiolo grapes from Piemonte.

Guests can enjoy a housemade egg yolk pasta made with white truffle butter and Parmigiano Reggiano cheese; pizzas topped with truffle oils; or a fried chicken breast that's accompanied by a black truffle cheese sauce. It's decadent stuff, but if you're dining at Eataly, you know what you're in for.

If you're ready to go all-in, Eatly's pop-up is also offering a "Truffle Experience" tasting menu that includes black truffles atop antipasto, white turffles atop pasta and a housemade chocolate gelato in a chocolate shell, starting at $95. You can add a couple of wine pairings to the mix for $35.

  • Things to do
  • Lake View

Chicago's only Hanukkah-themed pop-up bar takes over The Graystone Tavern in Wrigleyville for a third year, filling a weatherproof patio with more than 14,000 blue-and-white lights, dreidel ornaments, lighted menorah and a Hanukkah sweater wall (among other festive bits of decor). Dine on Hanukkah classics like latkes and matzo ball soup alongside not-so-classic options like a brisket egg rolls and a boozy, vodka-infused jelly donut. Pair your meal with a novelty cocktail—we're going with the strawberry puree-flavored Mensch Mule. Chag Sameach! 

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  • Bars
  • West Loop

The sprawling outdoor space at Lou's Backyard in the West Loop gets dressed up for the holidays with string lights, Christmas trees, inflatable snowmen and more whimsical touches. Pose for photo ops, order from the seasonal food menu (including options like chef's s'mores pie topped with melted chocolate raspberry coulis) or warm up with a themed cocktail or two—the Verte Chaud, which pairs housemade hot chocolate with Green Chartreuse and a blend of winter spices, is an especially cozy choice. 

  • Museums
  • Natural history
  • Museum Campus

Explore the colors of the natural world in the Field Museum's latest exhibition, which examines the meaning and function of some of the brightest hues in the world. “Wild Color” explores how plants and animals use color to ward off predators or attract maters, and how the color of gems and minerals can offer clues about their formation. The 7,000-square-foot exhibition is filled with specimens from the Field Museum's extensive collection, including a platypus that fluoresces under UV light and birds in every color (including "super black").

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  • Art
  • Mixed media
  • Suburbs

A deft collage artist who has created pieces for Lou Reed and Steve Earle as well as public installation in CTA stations, Tony Fitzpatrick is hosting his final museum exhibition. While he's not putting down his paintbrush for good, "Jesus of Western Avenue" offers one last chance to see a new collection of multimedia works by the artist, with more than 60 new creations on display. Presented by the Cleve Carney Museum of Art on the College of DuPage campus, the exhibit is housed not far from where Fitzpatrick began making art, acting and writing poetry. 

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  • Art
  • Contemporary art
  • Lower West Side

The National Museum of Mexican Art's annual Day of the Dead exhibit holds special significance this year, honoring the thousands of Mexican and American individuals who have died during the COVID-19 pandemic. "Día de Muertos" gathers a collection of artworks and installations, including a piece by Pilsen muralist Hector Duarte and an ofrenda for Adam Toledo, the 13-year-old student who was shot and killed by the police last year. As usual, admission is free—anyone is welcome to stop by the museum and pay their respects to those who are no longer with us.

  • Museums
  • Music
  • Near South Side

A musician who introduced traditional Indian styles of music and instruments to Western audiences, Ravi Shankar earned the title of "the Godfather of world music" from George Harrison of the Beatles. This exhibition at the South Asia Institute examines his career and the impact he had on popular culture, assembling more than 100 items, including rare concert posters, photographs, videos, record covers and personal ephemera. Guests can explore the collection, listen to the sitarist's music and gain a deeper appretiation for Shankar's creative output as well as his influence on the likes of Phillip Glass and John Coltrane.

The South Asia Institute will offer free admission to the exhibition every Friday.

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  • Time Out Market
  • West Loop

Want to watch the Bears play on a big, big screen? Time Out Market Chicago's screen is 32 feet wide by 6 feet tall, and you'll be able to watch every single game on it. And in addition to chicken wings, stacked burgers and saucy barbecue platters, you'll also be able to take advantage of select half-price draft beers and $20 beer buckets during every matchup. Plus, if a game falls on a Sunday, $10 Bloody Marys will also be available. There's no need for a reservation—just show up ready to feat while you cheer on the Bears!

  • Museums
  • History
  • Skokie

Tracing the contemporary gay rights movement back to the June 1969 police raid of the Stonewall Inn in New York City, the Illinois Holocaust Museum's hosts an exhibtion that documents a continuing struggle for equality. On loan from the Newseum, “Rise Up: Stonewall and the LGBTQ Rights Movement,” collects more than 85 artifacts, such as posters from Harvey Milk’s campaign for public office in San Francisco and the gavel Nancy Pelosi used to announce the repeal of “don’t ask, don’t tell.” Visitors will learn about the history of the LGBTQ community through pivitol moments in history and in popular culture.

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  • Things to do
  • Exhibitions
  • Streeterville

Get lost in a world of Wockets and Truffula Tree contained within this immersive experience, inspired by the literary works of Dr. Seuss. Bringing to life the characters and landscapes of books like The Cat in the Hat and The Lorax, "The Dr. Seuss Experience" is filled with a series of rooms where guests can interact with characters and snap photos. At the center of the pop-up, there's a maze inspired by Oh, the Places You’ll Go! made up of thousands of suspended balloons. Taking over 25,000 square feet on the street level of Water Tower Place, this experience is great for kids—or for embracing your inner-child.

  • Art
  • Photography
  • Grant Park

Explore the small-but-mighty works of photographer André Kertész, who arrived in Paris in the fall of 1925 with a camera and what was left of his savings. Over the next three years, the majority of the photos he produced were printed on postcard paper, making them easy to share with friends and benefactors. Exhibiting a collection of these small-scale works, the Art Institute's latest exhibit explores Kertész's output in the years before he graduated to international exhibitions and magazine spreads.

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  • Art
  • Photography
  • Loop

There are more guns than people in America, making it the most heavily-armed country in the world. “American Epidemic: Guns in the United States” collects photos from 10 different photographers that contemplate the violence, trauma, racism and other issues that arrise in a society where shootings are commonplace. You'll find images by Carolyn Drake, Nancy Floyd, Stephen Foster, Andres Gonzalez, Félix González-Torres, Deborah Luster, Zora J Murff, Renée Stout, and Hank Willis Thomas and Kambui Olujimi in the exhibit. If you're going to visit, make sure to secure a timed reservation via the Museum of Contemporary Photography's website. 

  • Art
  • Painting
  • Streeterville

Los Angeles–based artist Christina Quarles paints bodies, but not in the way you'd expect. Instead of straightforward studies of the human form, her canvases demonstrate a disregard for gravity and anatomy that finds torsos, limbs and faces arranged in surreal ways. This Museum of Contemporary Art show is her largest exhibition yet, focusing on her output over the past three years, including a large-scale installation that incorporates illusions.

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  • Theater
  • Experimental
  • Uptown

For more than 30-years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. Returning to in-person programming (attendees must be vaccinated and masked) after more than a year spent in the virtual realm, the company's signature show is more unpredictable than ever, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

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  • Art
  • Contemporary art
  • Grant Park

Don't call this one a retrospective. Yes, the Art Institute's exhibition of Barbara Kruger's work encompasses four decades of her career, but "THINKING OF YOU. I MEAN ME. I MEAN YOU." isn't stuck in the past. Instead, the display takes Kruger's vintage works and presents it alongside new pieces that build upon them, unlocking new context and meaning. Spread throughout the museum, guests will find rooms wrapped in Kruger's imagery, installations in the Regenstein galleries and pieces that inhabit the exterior walls of the museum (as well as billboards, bus stops and storefronts around Chicago). Expect to see Kruger's biting sense of humor on display—often spelled out in big, bold letters.

  • Things to do
  • Festivals

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This year's edition takes place across three months, filling vacant lots with site-specific architectural projects and presenting a pair of exhibitions at the Bronzeville Artist Lofts and the Graham Foundation. The theme of this year's Biennial is "The Available City," presenting projects and conversations that respond to and expand upon the question of "who gets to participate in the design of a city?"

Highlights of this year's programming include a circular outdoor meeting space designed by Matri-Archi(tecture) in a lot on 63rd Street in Woodlawn and a pair of exhibitions at the Bronzeville Artist Lofts and the Graham Foundation that feature projects by a global group of architects and designers, hailing from New York, Porto, Paris and Beijing. Plus, a series of Activation Weekends will activate the various Biennial installations throughout the city, welcoming performers, experts and cultural programming.

Stay up-to-date on the latest programming and activations by visiting the Chicago Architecture Biennial website.

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  • Museums
  • Natural history
  • Museum Campus

One of the Field Museum's most popular traveling exhibitions (which debuted in Chicago in 2014) returns home, using interactive displays to showcase how the bodies of animals operate much like machines. Visitors can use a pump to see how a giraffe's heart is able to send blood all the way up its neck or take in footage of a cheetah running to see how it's able achieve incredible speeds.

  • Things to do
  • River North

With more than 60 neon- and light-based installations spread throughout a gallery space, the Neon and Light Museum assembles an impressive collection of glowing artworks. Gaze at creations from the likes of conceptual artist Bruce Nauman or multimedia artist Monika Wulfers and snap a couple photos while you're at it. A series of hanging rods by Wulfers is the most immersive work on display, allowing viewers to stand in the middle of the work, but smaller works like a neon piece attributed to John Lennon (yes, the one from The Beatles) and a moving light sculpture by Gary Justic are equally intriguing.

The Neon and Light Museum was recently extended through December 15, giving you a few more weeks to bask in its glow.

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  • Art
  • Contemporary art
  • Streeterville

The Museum of Contemporary Art Chicago presents a survey that encapsulates two decades of work by Pakistani artist Bani Abidi, a former student at the School of the Art Institute of Chicago. Known for her video, photography and sound works, Abidi satirizes displays of power and nationalism as she explores the geopolitical relationship between India and Pakistan as well as the historical power struggles of South Asia. The exhibit takes its name from Abidi's watercolor series "The Man Who Talked Until He Disappeared," which depicts writers, political leaders and bloggers from Pakistan that have disappeared over the past decade.

  • Theater
  • Experimental
  • Lake View

Since 1997, a trio of performers covered in bright blue paint have headlined the Briar Street Theater in Lakeview. The Blue Man Group's show has evolved throughout the years, incorporating new compositions, narratives and state-of-the-art technology. But at its core, this production is all about combining percussion, music, physical comedy and buckets of brightly-colored paint in ways that make you want to jump out of your seat and dance along to the beat.

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  • Things to do
  • Exhibitions
  • Loop

Looking for a less conventional kind of escape room to check out in Chicago? Visitors are tasked with deciding the fate of a man accused of murder in this new, multi-room immersive experience in the South Loop, which uses projections, live actors and other tools to challenge the internal biases involved in our day-to-day decisions as well as the criminal justice system.

Located inside the Roosevelt Collection Shops, the 90-minute experience takes visitors through a weaving set of storylines and sets in a Clue-like pursuit of figuring out who's responsible for a crime; in the process, the exhibit explores elements racism, ageism, classism and other social issues that affect the criminal justice system. Visitors will have an hour to examine the case and come to a decision and then an additional 30 minutes for photo opportunities. 

  • Art
  • Design
  • Loop

Comic artist and author Chris Ware and historian Tim Samuelson curate an exhibition devoted to the early days of the comic strip. Showcasing work from the period of 1880 to 1960, the exhibit includes early strips that ran in newspapers as well as work by African-American cartoonists and publishers. The exhibit also pays tribute to Frank King, who penned "Gasoline Alley," creating one of the very first autobiographical comics based on real Chicagoans and the neighborhoods they lived in. If you've already seen the Museum of Contemporary Art's “Chicago Comics: 1960s to Now” exhition, this show will give you an even deeper understanding of the artforms ties to the Second City.

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  • Time Out Market
  • West Loop

Every Sunday from 11am to 3pm, Time Out Market Chicago's chefs offer a variety of delicious brunch dishes, from Hangover Ramen with shrimp and smoked pork to a stack of Buttermilk Pancakes layered with whipped mascarpone. Order as much as you want, grab a mimosa pitcher from the bar and stick around from 1 to 3pm for a set of tunes from the Chicago Soul Jazz Collective. 

  • Comedy
  • Uptown

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

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  • Theater
  • Circuses & magic
  • Loop

Enjoy dinner and show on the 14th floor of the Cambria Hotel at Teatro ZinZanni, a 2.5-hour experience that combines circus acts, comedy, cabaret and a meal curated by Debbie Sharpe—the Goddess of The Goddess and Grocer. The show takes place in an ornate, circular theater (designed to resemble a Belgian mirror tent) where the audience surrounds the stage. Guests dig into a four course meal while watching as comedians, aerialists, acrobats, singers and dancers perform amazing feats and catchy tunes. It's somewhere between Cirque du Soleil and a traditional cabaret show, with restaurant-quality refreshments.

Performances take place every evening, Wednesday through Saturday, with a special brunch matinee at noon on Sundays. You can find menus, wine and cocktail lists on the Teatro ZinZanni website.

  • Shopping
  • Markets and fairs
  • West Loop

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) every Sunday, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

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  • Comedy
  • Stand-up
  • Logan Square

Now housed in the space on Milwaukee Avenue in Logan Square, the country's longest countinuously running independent comedy showcase continues every Friday and Saturday night. Boasting alumni like Cameron Esposito, Kumail Nanjiani and Hanibal Buress, this stand-up show will introduce you to fresh new faces that may end up starring in Marvel movies or becoming podcast mainstays. Snag an affordable ticket, avoid the two-drink minimum and prepare to laugh your ass off.

  • Sports and fitness
  • Running

Go for a run and replentish your electrolytes with a beer during this series of 5K walks and runs, that take place at breweries throughout Chicago (and beyond). All of the Illinois Brewery Running Series events are untimed fun runs, more focused on camaraderie than competition. Participants at each event recieve a free beer, glassware or seasonal swag item, plus access to post-run events that feature live music, food, goodies from sponsors and giveaways. Check out the complete schedule of events on the Illinois Brewery Running Series website.

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  • Art
  • Sculpture
  • Suburbs

See five towering sculptures by South African artist Daniel Popper at the Morton Arboretum's new outdoor exhibition, which spreads the 15- to 26-foot-tall works throughout the natural area. Made of glass-reinforced concrete, wood, fiberglass and steel, the one-of-a-kind pieces in "Human+Nature" depict human figures that evoke the natural landscape they're set amid, including a pair of 36-foot-long hands reaching out from a grove of oak trees and a maternal figure that springs up amid magnolia trees.

Access to "Human+Nature" is included as part of timed-entry admission to the Morton Arboretum, and there's a map that will allow you to easily plan your visit and spot all five of the sculptures along the way.

  • Art
  • Photography
  • Lincoln Park

The Chicago History Museum welcomes a fascinating multimedia exhibition of more than 65 pieces from the celebrated street photographer. Known for beautifully capturing everyday moments, each of the shots on display here was taken when Maier was a suburban Chicago nanny from the ‘50s to the ’70s. Most of them have never been on display, and feature alongside film clips, quotations, and sound bites that help to bring Maier’s incredible work further to life.

‘Vivian Maier: in Color’ opens May 8 2021. Admission is included in the Chicago History Museum entry price. For more information head to www.chicagohistory.org/exhibition/vivian-maier-in-color

Written by Time Out. Paid for by Chicago History Museum

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  • Art
  • Installation
  • West Loop

The home of Chicago's only Infinity Mirror Room (created by Japanese Yayoi Kusama) is open to the public once again, presenting a new collection of one-of-a-kind art installations alongside some old favorites. New additions to WNDR Museum include a multi-sensory experience from S̶A̶N̶T̶IA̶G̶O̶X that uses artificial intelligence, sounds, visuals and scents, as well as an installation called I Heard There Was a Secret Chord that allows guests to become part of an evolving virtual choir.

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