The best things to do in Chicago this week

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. Reservations for the popular ice rink should be made in advance, as they tend to fill up quickly.

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 an illuminated 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. 

More than two million lights cover the trees, fences and structures in the Brookfield Zoo at this annual holiday event, which is now in its fourth decade. Guests can walk through a 300-foot-long tunnel featuring colored lights synchronized to music, spot larger-than-life illuminated animal sculptures, gaze up at a 41-foot-tall lit tree and warm up with concessions such as funnel cakes, pizza, spiced wine and hot cocoa. 

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's offseason. The Wrigley Field-adjacent space hosts a variety of seasonal activities, including photos with Santa, a winter market, carnival rides and holiday movie screenings. Opening on November 23, you'll be able to shop for gifts, sip a hot beverage and enjoy delicious treats through December 31. Visit the Winterland website for hours and additional information about programming.

This immersive, multi-level Christmas pop-up bar boasting wall-to-wall holiday decor returns to Wrigleyville, taking over Stolen Saddle during the most festive time of the year. You'll find photo ops galore as well as drinks decked out with decorative garnishes and garlands, including large-format cocktails. Feeling hungry? Feast upon festive options like Santa's Smash Burger, Festive Fry Flight and Grinch Shake. Don't forget to snag a reservation before you head to Santa Baby—families are welcome to stop by during the day, but after 8pm it's 21+. For full holiday hours, check Santa Baby's website.

The night after Christkindlmarket opens and the city's Christmas tree is illuminated, the Magnificent Mile rings in the holiday season with its annual parade. Beginning at 5:30pm, you'll be able to watch lights in more than 200 trees along Michigan Avenue sparkle as a procession of floats, giant helium balloons, marching bands and celebrities pass by. As usual, Mickey Mouse and Minnie Mouse will act as the Grand Marshals. 

The iconic German-inspired holiday market at Daley Plaza brings just over a month of Christmassy celebrations to the Loop. Browse stalls stocked with handmade gifts, German food and plenty of hot beverages to keep you warm while you wander around and soak in the festive atmosphere. Don't leave without trying spiced glühwein, a German hot wine concoction that's best enjoyed in the market's famous boot mugs.

Wander around with a Bloody Mary in hand at the annual holiday iteration of Randolph Street Market, which always boasts an eclectic smattering of vendors selling vintage furniture, handmade clothing, art, antiques and more treasures guaranteed to make for a memorable gift.

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. The company's signature show is more unpredictable than ever these days, 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.

Frosty's Christmas Bar near 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 well past midnight every night of the week. Don your favorite holiday attire and enjoy a glass of something boozy and marshmallow-topped while eating Christmas cookies amidst the twinkling lights, tinsel and over-the-top decorations.

Ready to get into the holiday spirit? The Morton Arboretum's annual holiday light show returns for its 13th anniversary as a mile-long, walk-through spectacle of LED lights and music, featuring a blend of new and returning light displays set amid 50 acres of trees. Back again this year is "Electric Illumination," a series of late-night parties with DJ-curated playlists that will synchronize progressive house and '80s dance beats with the light shows, as well as "IllumiBrew," a special evening where guests can sample beers and ciders from local breweries. 

The Whistler’s monthly lit series pops up on the second Wednesday of every month, bringing an evening of readings, workshopping and discussion to the Logan Square cocktail bar. Each show is followed by an installment of the Relax Attack Jazz Series, a free event with a constantly rotating bill.

Planes, Trains, and ??? is a musical tribute to one of the most beloved holiday movies of all time. With plenty of nods to the John Hughes classic, this improvised show is packed with big laughs and a whole lot of heart. With Second City’s signature improv and a soundtrack that’ll have you shimmying in your seat, Planes, Trains, and ??? promises the perfect escape from the holiday blues.

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 7:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

Every local thrifter worth one's salt knows that Vintage House Chicago holds some of the city's best thrift scores. The bimonthly vintage and handmade market showcases local makers at rotating venues throughout the city. Each market features a new lineup, so you can plan on finding something new every time.

In honor of the 50th anniversary of filim critic duo Gene Siskel and Roger Ebert's partnership, the Chicago Cultura Center is revisiting their favorite “hidden gems” films. Throughout November, audiences will view Siskel and Ebert's most cherished films—ranging from coming-of-age dramas to indie thrillers—and hear post-screening conversations with an array of speakers, including Ebert's widow Chaz. 

Peter Shaffer's 1979 masterwork brings to life the rivalry between composers Antonio Salieri (Ian Barford) and Wolfgang Amadeus Mozart (David Darrow). Salieri is the Court Composer and the established standard of the day—his compositions are palatable, albeit restrained. Enter Mozart, a wild child prodigy with climbing notoriety and the ability to make music like no one has ever heard. Mozart's music moves Salieri to tears, but also awakens a destructive jealousy that compells him to supress Mozart at every turn. 

The weather outside might be frightful, but you'll be plenty cozy inside JoJo's Shake Bar, which has transformed every inch of its outdoor patio into a Winter Wonderland decorated with an eight-foot tall nutcracker, giant ornaments and thousands of string lights. Treat yourself to over-the-top shakes—such as the Winter Wonderland Shake, which is peppermint flavored and topped with cookies, marshmallows, a candy cane and a snowman made of donut holes—and fanciful seasonal cocktails like Santa's Sangria, and be sure to grab a table close to the pop-up's Christmas tree. 

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. 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. 

Every year, the Griffin Museum of Science and Industry puts up its four-story Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors will be able to take in even more seasonal cheer at the accompanying Holidays of Light exhibit, which recognizes the traditions of Chinese New Year, Diwali, Kwanzaa, Ramadan, Hanukkah, Visakha Puja Day and St. Lucia Day. 

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

Sue the T. rex hosts a sleepover! Families with kids ages 6–12 can bring their sleeping bags for a night at the museum. Kids can explore various exhibits after dark, play games and cozy up by the giant dinousaur for bedtime stories. The fun doesn't end at bedtime: Grab your flashlight and explore the halls as the lights go out. 

A spot on the pine bleachers at Drip Collective has become one of the most coveted seats in the city, thanks to the cafe's adventurous beverage menu (hello, mango sticky rice matcha latte!) and hyper-local event programming. Aside from piping hot coffee, Drip has been bringing a different kind of heat this summer with Hot Drip Sessions, a weekends-only DJ pop-up. 

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder.

Every Wednesday, the Adler stays open late from 4–10pm so that folks can visit after work or school—best of all, admission is free for Illinois residents. Escape the planet with exhibits about the first lunar missions, the solar system and more, plus sky shows in an immersive dome theater. 

“Take Care with Peanuts: The Exhibit” is an immersive fan experience inspired by a global initiative of the same name. Based on the captivating world depicted in Charles M. Schulz’s iconic comic strip, the exhibit brings the beloved Peanuts gang to life through interactive displays and hands-on activities promoting self-care, empathy and environmental stewardship. 

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world.

Not sure where to start? Check out our first-timer's guide to the exhibition. Stay up-to-date by visiting the Chicago Architecture Biennial website.

With soundstage-sized pieces like horned sculptures emitting soap bubbles, inflated spheres bedecked in abstract squiggles and surreal faceless figures hovering in space, “EmotionAir” reimagines the humble balloon as any other artistic medium—a conduit for creativity and emotion. 

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.

--