Shannon Shreibak

We’re probably not alone in saying that the weekend is always on our minds here at Time Out Chicago HQ. Like you (probably), we spend the workweek daydreaming about the next restaurant to obsess over and obsessively updating our concert calendars. Whether you’re museum-hopping, plotting a day trip to escape the city, or ready to ghost your original plans for something spontaneous, you’ll find plenty of ways to make the most of your weekend in Chicago. Last updated January 27, 2026: Looking for the best things to do in Chicago this weekend? Whether you’re the designated group chat planner or seeking some last-minute inspiration, we’ve got you covered. This weekend’s highlights include the annual Chicago Boat Show, Chicago Restaurant Week and the world-renowned Chicago International Puppet Theater Festival. On a budget? We’ve rounded up some of the best free events in Chicago, too. Scroll down to discover the best events across the city! RECOMMENDED: The best things to do in Chicago today RECOMMENDED: The best free things to do in Chicago this month RECOMMENDED: The best cheap eats in Chicago RECOMMENDED: Discover the 50 best things to do in Chicago right now

If you're looking for the perfect arrangement to spruce up your home or to give to that special someone on Valentine's Day, look no further than the many expert florists right here in Chicago. From hip, new flower shops to decades-old family-run plant stores, all of these shops offer an abundance of colorful bouquets and impressive arrangements. Prepping for a special occasion? Most of these options offer same-day flower delivery, too. So whether you're adding some character to your dining-room table or expressing your appreciation for a loved one, these flower shops in Chicago are sure to get the job done. RECOMMENDED: Sweeten the deal with the best chocolate shops in Chicago

The Windy City is filled with beautiful parks, bustling shopping districts and dramatic outdoor art installations, but when it’s raining or snowing, you shouldn't let it ruin your day. There are world-class museums where you can explore everything from dinosaurs to modern art, relaxing spas for self-care, plus active fun to be had like bowling, bouldering and table tennis. So don’t let the weather get in the way of having a great day and stay warm and dry by enjoying some of the best things to do indoors in Chicago. RECOMMENDED: The best things to do in Chicago

Last updated January 26, 2026: Whether you’re checking out the Chicago International Puppet Theater Festival, savoring the last few weeks of Yoko Ono's career-spanning retrospective at the Museum of Contemporary Art or tasting your way through Chicago Restaurant Week, there’s plenty to look forward to this week. Even on a budget, you can take advantage of free admission days at several Chicago institutions or go ice skating under the skyline at Millennium Park. Read on for our curated guide to the best events happening around town this week. RECOMMENDED: Discover the best things to do in Chicago in January 2026

Last updated October 28, 2025: Fall in Chicago is officially underway, which means it's time to turn your attention to all things spooky, ghoulish and pumpkin-filled. Hoping for a fright? Visit one of Chicago's most haunted places, attend one of the city's many Halloween parades and parties or wander through a ghostly haunted house. No matter your age, embrace the thrills and chills of spooky season with our guide to the best Halloween events in Chicago this year.  RECOMMENDED: Our complete guide to Halloween in Chicago Read more: The 40 greatest Halloween songs for the ultimate spooky party The 12 best Halloween events in the USA for 2025 The 48 best Halloween movies of all time

The official start of fall in Chicago might be in September, but the season doesn't really hit its stride until October—a month replete with crisp air, colorful fall foliage and a heaping helping of spooky fun. Take advantage of everything autumn has to offer by exploring the best pumpkin patches near Chicago, attending an apple-themed neighborhood fest, getting lost in corn mazes or staring up at the changing leaves at your local park or garden. And of course, celebrate Halloween in Chicago with spooky pop-ups, haunted houses, horror movie marathons and even more ghoulish events. Ready to embrace autumn? Check out the rest of the best things do to in Chicago this October.  RECOMMENDED: Events calendar for Chicago in 2026

Chicago might be known as the Second City, but our attractions are first-class. Need evidence of that fact? Look no further than the many Chicago museums, where you'll find everything from the best-preserved T. rex skeleton ever found to paintings by Van Gogh and Picasso. Or take a stroll through our gorgeous parks and gardens, home to some of the best public art in Chicago (say hello to "The Bean"). You can also laugh it up at a comedy club, see a show at a jazz club once frequented by Al Capone or have a Michelin-starred meal at one of the best Chicago restaurants ... the list goes on. From first-time visitors to lifelong Chicagoans: we’ve handpicked the city’s must-see spots so you can experience the very best of Chicago. RECOMMENDED: The best things to do in Chicago right nowRECOMMENDED: The best cheap things to do in ChicagoRECOMMENDED: The best hotels in ChicagoRECOMMENDED: The best boutique hotels in Chicago This article includes affiliate links. These links have no influence on our editorial content. For more information, click here.

Get excited, Chicagoans, because winter in Chicago is almost over and some of our most beloved events and traditions are happening this month. First up is St. Patrick's Day in Chicago, which is once again bringing river dyeing festivities and a parade to the Loop, along with plenty of other celebrations across the city (including the Shamrock Shuffle and parades on the South and Northwest Sides). Hoping to avoid the crush of green-clad people downtown? Check out some inspiring exhibitions at The Art Institute of Chicago, visit David Byrne's “Theater of the Mind” installation or feast on encased meats and beers at Haymarket's Sausagefest. You'll find all that and more in our roundup of things to do in Chicago this March. RECOMMENDED: Events calendar for Chicago in 2026

It may be the shortest month of the year, but you'll find that February is still jam-packed with stuff to do in Chicago—especially because some of the city's most beloved annual events will be taking place. Grab discounted tickets to acclaimed shows during Chicago Theatre Week or check out the latest and greatest vehicles at the Chicago Auto Show. You can also woo your significant other on Valentine's Day in Chicago or celebrate the Lunar New Year with parades and festive dinners. Looking for even more stuff to do? Get ready to make the most out of the month of love with our February 2026 events guide. RECOMMENDED: Events calendar for Chicago in 2026

No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. The best things to do in Chicago run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Chicago museums. Hungry? You've come to the right place, because Chicago is famous for its delicious cuisine. There are tons of amazing restaurants in Chicago that highlight the city's rich and diverse culinary landscape. (And plenty of uniquely Chicago bars that do the trick, too.) We've searched all across the city to assemble this list of the best things to do in Chicago. Follow it and never get bored here again. Quick picks: The best things to do in Chicago Millennium Park – See “The Bean” (Cloud Gate) and coast along one of the city's most stunning ice rinks Art Institute of Chicago – World-class collection with strong Impressionism and modern art wings ($26–$32) Willis Tower Skydeck and “The Ledge” – Enjoy sky-high views and step onto glass ledges above the city ($36–$45) Last updated January 22, 2025: Chicago has shifted into full winter wonderland mode, offering a wealth of things to see and do this winter. Whether you're interested in exploring iconic sights, diving into culture or embracing the season's cozy energy, the city has you covered. Read on to discover the best activities for kicking off the year. You can also find out more about how Time Out selects the very best things to do all over the world

Winter in Chicago can quickly devolve into a barrage of frigid temperatures, slushy streets and icy sidewalks—but that doesn't mean giving up on the best things to do in Chicago. Throw on some layers and scope out the many things to do outdoors this winter, like strolling through a snow-capped park, shredding across ice rinks and admiring icicle-adorned public art. Sure, there are plenty of fun things to do indoors, but you don't need to stay cooped up until spring arrives—here's where you can find the best things to do during winter in Chicago. RECOMMENDED: Discover more with our ultimate guide to winter in Chicago

As Chicago's blazing summer yields to cool climes and autumnal coziness, it's time to head back to your favorite Chicago museums. Illinois Free Days are back, offering free admission to the city's world-class exhibitions—from the Art Institute of Chicago to the Shedd Aquarium—for state residents on select days. (Word to the wise: Don’t forget your proof of residence.) Plus, Chicago Public Library cardholders can score various museum passes and other benefits. While perks abound for Illinoisans, there are still options for out-of-towners to enjoy free admission year-round. Take a look at our roundup below, and pencil in your next Chicago adventure. RECOMMENDED: Discover more of the best things to do in Chicago

Lilliput Books is an Asian, woman-owned independent bookstore that emphasizes community and curation. The cozy shop's collection includes titles in Chicago history, LGBTQ+ selections, nature, fiction and nonfiction as well as a wide selection of book-adjacent gifts and books for kids of all ages. In addition to its wide selection of tomes, Lilliput also hosts monthly events lik silent book clubs, junk journal and vision board workshops and Sunday morning yoga sessions. Home to a popular and beloved shop dog, Lilliput is dog-friendly and offers dog treats for furry visitors.

Wanna relive the thrill of punishing a captive audience like you did during grade school show-and-tell? Then Show & Tell for Grownups is the place for you! Once a month, comedians, storytellers and everyday passionate folks gather to share their quirky, heartfelt or downright fascinating interests. Each presenter gets five minutes on the clock to wax philosophical about their obsession, then it’s the audience’s turn with a quick Q&A. Think of it like falling down a Reddit rabbit hole—only live, and way more fun. Feeling especially brave? Sign up for your five-minute show-and-tell slot here.

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.

Multimedia artist Yoonshin Park challenges conventional ideas of what books are—and what they can be. Prompt and Prompted presents new and ongoing works that reimagine artist books as spatial, symbolic and participatory sites, engaging ideas of memory, marginality, translation and transformation.

How are some of the most iconic costumes of the past century made? Costume designer Paul Tazewell pulls back the curtain in this behind-the-scenes exhibition. Highlights include costumes from Wicked, Janelle Monáe’s MET Gala looks and Steven Spielberg’s West Side Story. Sketches, videos and narration reveal how imagination becomes wearable art.

This family-friendly exhibition explores six habitats—Desert, Ocean, Rainforest, Sky, Woods and City—through the eyes of modernist artist Charley Harper. Designed to foster appreciation for biodiversity and interdependence, the exhibit includes interactive games, a DIY soundscape station and multisensory interpretations of Harper’s beloved work.

Thanks to a landmark donation from the family of Lee Kun-Hee, the late chairman of Samsung Group, Chicagoans will be able to view extraordinary Korean artworks once held in private collections. Spanning painting, ceramics and Buddhist sculpture, the exhibition includes 140 works that trace two millennia of artistic legacy—22 of which are officially designated National Treasures or Treasures by the Korean government.

The Museum of Contemporary Photography celebrates its 50th anniversary with a sweeping look at its collection. Each of the museum's five galleries will represent a decade of collecting, beginning with its most recent acquisitions (2016-2026) in the first gallery, then rewinding through time. The retrospective features rarely exhibited and newly acquired works by influential photographers including Dorothea Lange, Harry Callahan and Robert Frank.

As the Driehaus Museum’s first artist-in-residence, Brendan Fernandes will transform the Murphy Auditorium into a dynamic site for sculpture, movement and sound. Inspired by the Judson Dance Theater, Fernandes’ Scores for the Murphy Auditorium will unfold as an episodic residency throughout 2026, with performances and public programs announced over time.

This first-of-its-kind exhibition at the Museum of Contemporary Art Chicago explores the visual, political and spiritual histories of dancehall and reggaetón through contemporary art. Once grassroots scenes, both genres have become globally influential movements tied closely to sexual and political liberation. The show features works by more than 35 artists, including Jean-Michel Basquiat, Edra Soto, supakid and Lee “Scratch” Perry.

This exhibition poses a devastatingly powerful question: What if Emmett Till had not been brutally lynched in Mississippi in 1955? Through photography, the exhibition imagines an alternate history in which Till lived—moving from images inspired by the last meal his mother packed before his trip south to meditations on the life he might have experienced, from the rise of the Chicago Bulls to the ongoing fight for civil rights.

Drag Race: The Experience has sashayed into Chicago for a one-month stint. But does it bring the requisite charisma, uniqueness, nerve and talent? Well… yes and no. Produced by World of Wonder—the company behind Drag Race and the global DragCon conventions—the attraction casts visitors as the main character inside some of the show’s most iconic spaces. You can strut the Main Stage, snap a selfie in the Werk Room, film a confessional and flip through racks of costumes pulled straight from the runway. There’s never-before-seen footage playing across a glowing wall of retro TV screens, an abundance of photo ops and QR-guided prompts that politely boss you from room to room. Guests are given a unique QR code to use with the scanner in each room, enabling them to collect photos throughout their visit. The layout isn’t especially intuitive, but if you approach it as one giant, glittering selfie machine, the whole thing snaps into relative focus. There are costumes, clips and even a full Snatch Game set, ready for you and your friends to butcher celebrity impressions with enthusiasm if not accuracy. The experience ends in an atrium where you can retrieve your photos, sip a drink at the Gold Bar, shop exclusive merch (yes, including a “shantay” fan) and attempt a Best Friend Race-style scavenger hunt. During its run, Drag Race: The Experience will host screenings and premiere parties across the Drag Race universe. The space is also rentable for private events, which may be when it t

Thanks to its earnest portrayal of queer love and longing (not to mention that now-legendary Wolf Parade needle drop), the hockey drama Heated Rivalry has become a bona fide cultural sensation. What began as a story about rivals on the ice has grown into something much bigger, inspiring feverish Reddit threads, heaps of bootleg merch and some truly inspired community events. Whether you’re a Shane or an Ilya—or still arguing about which one you’re supposed to be—these events offer a rare chance to connect with other Heated Rivalry fans who share your devotion to the game, the drama and, of course, the big feels.  Your guide to Heated Rivalry events blazing through Chicago Heated RivalRave House of Blues, 329 N Dearborn StJan 23 at 5pm and 10:15pm Nineties-themed promoter Club 90s is giving rave culture the Heated Rivalry treatment with Heated RivalRave, a night that cranks the energy all the way up. Expect a bumping, era-appropriate playlist, bold costumes and an atmosphere that leans hard into nostalgia and #Hollanov fiending. Whether you come dressed for the rink, the rave or something gloriously in between, this is a space to dance it out with fellow fans who know their beats as well as their hockey lore. Trivia Tuesday: Heated Rivalry Edition Sidetrack, 3349 N Halsted StJan 27 at 8pm Put your Heated Rivalry knowledge to the test at this special Sidetrack Trivia Tuesday takeover. From deep-cut moments to blink-and-you’ll-miss-it details, the questions will separate the cas

You likely recognize Glinda’s rhinestone-spangled pink gown from the Wicked films or Anita’s sunflower-yellow dress from Steven Spielberg’s adaptation of West Side Story—garments so vivid they feel as though they might still be hanging in a wardrobe somewhere, quietly judging your choice of winter coat. But do you know the man who masterminded the architecture behind these icons? I journeyed south to the Griffin Museum of Science and Industry to find out.  Enter Paul Tazewell, the subject of the MSI’s new exhibition, “Crafting Character: The Costumes of Paul Tazewell.” Open now through September 7, 2026, the show invites visitors behind the seams, tracing the frantic imagination and sheer, finger-pricking labor required to define modern film and Broadway. This is not merely a greatest hits rack of pretty clothes—though the sequins are out in full force—but a deep dive into the alchemy of how fabric becomes a person. The exhibition commences in a darkened room where Janelle Monáe’s MET Gala ensembles hold court like chic, unblinking sentries. From a screen, Tazewell’s polished and friendly visage explains that costumes are more than just fancy upholstery; they are storytelling tools that dictate how a character moves, speaks and is ultimately judged by the balcony seats. “Costume is a character made visible,” he declares, just as a pair of doors fold open to welcome us into his world. Photograph: Shannon Shreibak   Each room is studded with tender personal artifacts: a self-

Since the dawn of time—or at least since someone first glued string to a wooden limb—puppetry has been one of the world’s most polarizing art forms. Some find puppets downright adorable; others are still unpacking childhood trauma involving carved smiles and unblinking eyes. Chicago, however, has clearly chosen a side. The city’s appetite for puppets is downright ravenous, which is why the 8th Chicago International Puppet Theater Festival kicks off its 12-day takeover tomorrow, January 21. Now presented annually, the Chicago International Puppet Theater Festival corrals puppeteers from across the globe, including artists from England, France, Norway, Denmark, India, South Korea and Spain—and, of course, Chicago itself. The largest event of its kind in North America, the festival drew a record-breaking crowd last year, welcoming more than 22,000 attendees. These are people who willingly chose Chicago as a January travel destination, which tells you everything you need to know about the power of marionettes. The 2026 festival spans 12 days and dozens of venues across the city, transforming Chicago into a global pageant of felt, foam, wood and ingenuity. Alongside ticketed performances, there are free shows, exhibits and the always-buzzing Puppet Hub—a cozy headquarters featuring the Spoke & Bird Pop-Up Café (serving coffee, tea, winter soups and baked goods), a Pop-Up Puppet Shop and two free exhibits perfect for lingering. Photograph: Danny Kaan, Courtesy of Chicago Internati

The Chicago Bears—rightfully dubbed the “Cardiac Bears” this season thanks to their habit of winning in the final seconds—take on the Los Angeles Rams in a can’t-miss matchup. Whether you're watching from home, streaming on your phone or joining a crowd at a packed sports bar, this game promises non-stop action. Steel yourself for a classic NFL showdown. How do I watch the Bears vs. Rams game on TV? In Chicago, the game will be broadcast live on NBC 5 (WMAQ-TV). Kickoff is scheduled for Sunday, January 18 at 5:30pm CT. How do I stream the Bears vs. Rams game? There are several ways to stream the game: Peacock: Streaming live nationwide NBC App / NBCSports.com: Available by logging in with your TV provider credentials NFL+: Subscribers can stream the game live on mobile devices and tablets How do I listen to the Bears vs. Rams game on the radio? If you’re on the move, you can keep up with the game via the following broadcasts:  Local (English): ESPN Chicago (1000 AM and 100.3 FM HD2) featuring Jeff Joniak, Tom Thayer and Jason McKie Local (Spanish): Latino Mix 93.5 FM with Omar Ramos National: Westwood One Sports (Kevin Harlan and Ross Tucker) What are some of the best local watch parties?  Chicago’s Largest Watch Party Ramova Theatre, 3520 S Halsted StJan 18 at 2:30pm  Watch the game at Bridgeport’s historic Ramova Theatre as it hosts “Chicago’s largest watch party” with a 40-foot screen and food and drink specials—all free with RSVP. Just make sure to bring a folding cha

On a quiet city block lined with discreet brick buildings and manicured lawns, Chicago’s famed Candyland House slices through the gray-washed horizon like a blazing sugar rush. It’s the kind of place that makes joggers slow their pace and pretend to check their phones while sneaking a covert photo—a local landmark that inspires unbridled joy and ardent criticism in equal measure. Now, those opinions are going national: HGTV has officially dubbed the pastel-colored Victorian a contender for the Ugliest House in America. The home is featured in-depth during the show’s seventh season, the premiere of which is now available to stream on HBO Max and discovery+. The Candyland House (located at 1525 W Pratt Blvd) has long been a fixture of Rogers Park, and its history is as vibrant as its facade. For decades, it served as the residence of local artists Jackie Seiden and the late Don Seiden; the house became one of Jackie’s primary artistic outlets alongside her teaching career at institutions like the School of the Art Institute of Chicago. Their whimsical transformation of the home was even chronicled in the 2020 documentary So Late So Soon.  RECOMMENDED: HGTV just named the most beautiful garden in Illinois—and you probably won’t guess it View this post on Instagram A post shared by HomosWithHammers (@homoswithhammers) The property changed hands in 2022 when it was purchased by Joe Bergantino and Ricky Gonzalez, who document their restoration journey under

The observation of Martin Luther King Jr. Day on Monday, January 19, offers many a welcome three-day weekend. But while the extra rest is nice, the holiday is best spent honoring Dr. King’s enduring legacy of civil service and economic justice. Whether you’re looking to volunteer or visit one of the city’s cultural institutions, we’ve rounded up the best ways to celebrate Dr. King's life and the ongoing work of the civil rights movement. Many civic leaders encourage treating the holiday as a “day on, not a day off.” To find ways to give back to your local community, you can browse volunteer opportunities through Chicago Cares or the City of Chicago’s volunteer hub. RECOMMENDED: The best January 2026 events in Chicago The best Martin Luther King Jr. Day programming Chicago Sinfonietta: MLK Tribute Concert Auditorium Theatre, 50 E Ida B. Wells DrJan 19 at 4pm  Chicago Sinfonietta presents its annual Dr. Martin Luther King, Jr. tribute concert, this year honoring the legacy of Dr. Daniel Hale Williams. A pioneering Chicago surgeon, Dr. Williams made history in 1893 by performing the first successful open-heart surgery and founding the first Black-owned hospital in America. The program celebrates Dr. Williams’s dual legacy of medical innovation and social progress. King Day: Building Our Future The Art Institute of Chicago, 111 S Michigan AveJan 19 at 11am  Celebrate Dr. Martin Luther King Jr. at the Art Institute of Chicago’s Ryan Learning Center. The museum is hosting an after

The Tripadvisor Travelers’ Choice Awards 2026 are officially here, and Chicago has emerged as a major winner. In a showing that will surprise few locals, the Windy City swept three prestigious categories, landing in the top 10 for Top U.S. Destinations, Top Food Destinations in the U.S. and Top Trending Destinations Worldwide. As Chicagoans already know, our city is a year-round powerhouse. Whether it’s the glow of festive holiday markets, the high-octane energy of genre-spanning summer music festivals or our collection of world-class museums and attractions, there is a wealth of things to do no matter the season.  RECOMMENDED: The 25 best restaurants in Chicago, ranked Chicago secured the No. 6 spot for Top Destination in the U.S., solidifying its reputation as a powerhouse of food, culture and architecture. Proving its global appeal, Chicago also ranked No. 6 for Top Food Destinations in the U.S. and climbed to No. 3 for Top Trending Destinations Worldwide—a nod to travelers’ growing desire to explore the city's diverse neighborhoods and world-class dining. Tripadvisor specifically highlighted “must-do” experiences like the Chicago Architecture Foundation Center River Cruise. Led by expert docents from the Chicago Architecture Center, the cruise offers a blend of history and storytelling as guests view the city’s iconic skyline from an open-air boat. Other top-rated experiences included the Chicago Ultimate Food and Walking Tour and the breathtaking views from 360 Chicago.

At Time Out, we’re always scrutinizing our rankings to ensure they reflect the current pulse of the city. As we brace for yet another cold front in Chicago, we felt it was only appropriate to revisit our guide to Chicago’s best outdoor winter activities, reshuffling the list to highlight the seasonal essentials you shouldn’t miss right now. Along with adding some new activities that are keeping spirits high during the city’s most brutal season, we also reworked the rankings to reflect some new developments and exciting openings. As a result of our latest reporting, standing tall (and toasty) at the very top is our new No. 1: Kiln Floating Sauna. RECOMMENDED: This is the No. 1 winter getaway for Chicagoland families Photograph: Kari D'Acquisto, Courtesy of Kiln Floating Sauna At the tail end of 2025, Navy Pier debuted a unique winter haven: Kiln, a custom-built floating sauna bobbing in the shadow of the iconic Centennial Wheel. Founded by Chicago entrepreneur Zoe Lake, the Scandinavia-inspired vessel offers guided thermic cycles—alternating heat, cold and rest—against an unbeatable skyline backdrop. For the truly daring, the experience includes the ultimate “cool down”: a plunge directly into the frigid winter waters of Lake Michigan. When determining our rankings, we weighed selection and ambience against a more elusive metric: community-centeredness. Kiln perfectly embodies this spirit, acting as a restorative hub that makes the city feel smaller and reminds you exactly w

At Time Out, we’re constantly refreshing our rankings to ensure we’re championing Chicago’s absolute best—not just recycling outdated favorites. This month, we revisited our guide to Midwest family winter getaways and decided it was time for some big changes. In addition to scouting fresh destinations, we’ve reshuffled our rankings to reflect shifting travel trends and recent local developments. Based on our latest reporting, Holland, MI, has officially claimed the No. 1 spot as the ultimate winter escape for Chicagoland families. RECOMMENDED: The best kid-friendly restaurants in Chicago Blending small-town charm with cozy, kid-friendly adventures, Holland is the quintessential winter getaway for families. Spend your days sledding, admiring frozen windmills or bravely enduring the elements before retreating downtown to thaw out. When the summer crowds vanish and Lake Michigan transforms into a living snowglobe, the city’s charm truly shines. Wander through local favorites like the Apothecary Gift Shop to snag whimsical treasures, then take advantage of the quiet streets and affordable seasonal lodging. It’s a peaceful escape that stays warm long after the sun goes down. The perks don’t stop at the city limits, either. The equally enchanting town of Saugatuck is just a 20-minute drive from Holland. There’s no shortage of wintry activities in the captivating locale: Catch some air sledding at Mount Baldhead or Oval Beach, or strap on some snowshoes for a trek through the serene

January is a notoriously difficult time for Midwest concertgoers—shows are scarce and the conditions are even worse for touring artists. Musicians must brave grueling roads and coax fans out of warm homes despite subzero temperatures and post-holiday money hangovers. To bridge this gap, Tomorrow Never Knows was founded 20 years ago, masterminded by then-Schubas Tavern talent buyer Matt Rucins. Across four weekends in January, this wintertime music and comedy festival champions rising stars in the indie scene, placing them in intimate spaces like the cozy Hideout, the legendary Metro and the new Ramova Theatre in Bridgeport. Setting the event further apart is a multidisciplinary lineup that includes comedians like Ramy Youssef and drag artist Derry Queen. Rather than sticking to a single genre, the festival strives to capture the full breadth of the independent arts scene in Chicago and beyond. Past lineups have been remarkably prophetic, featuring early performances from Bon Iver, Caroline Polachek and Cameron Winter (of Geese). Given that track record, Tomorrow Never Knows attendees are likely to catch the next global sensation in some of the city's most storied rooms. When is Tomorrow Never Knows 2026? Tomorrow Never Knows takes place every weekend in January: January 8–10, 15–17, 22–24 and 29–31. Where is Tomorrow Never Knows 2026? The festival takes over eight venues throughout Chicago: Lincoln Hall, Schubas, Metro, GMan Tavern, Sleeping Village, Hideout, Color Club and R

At Time Out, we constantly refresh our rankings to ensure we’re championing the very best that Chicago has to offer—not just clinging to outdated favorites. This month, we revisited our guide to the city’s top 30 bookstores and felt compelled to shake things up. Along with adding some new bookstores that are keeping the literary scene alive and well, we also reshuffled the rankings to reflect some recent developments and the simple fact that cities, like reading habits, are constantly changing. As a result of our latest reporting, Pilsen Community Books has officially claimed the number one spot as the best bookstore in Chicago. RECOMMENDED: The best literary and poetry readings in Chicago Photograph: Jaclyn RivasPilsen Community Books As Chicago’s first employee-owned bookstore, Pilsen Community Books welcomes visitors with floor-to-ceiling shelves spanning every genre imaginable. True to its name, the shop prioritizes community through its dual subscription programs, regular events and “Pilsen Reads”—a local youth literacy initiative. And while the store is an ideal sanctuary for in-person browsing, its expertly curated website brings that same sense of discovery into your home. In determining our rankings, we weighed selection and ambiance against a more elusive metric: “community impact.” To put it simply, this is a place that stays with you long after you leave. Pilsen Community Books embodies the true Chicago spirit—earnest without being precious, opinionated without

As the ornaments come down and pine needles make their annual bid for independence, Chicagoans face the ultimate post-holiday question: What should I do with this tree? Whether you’re a pro-recycler or a first-timer, the city has a plan. While you could leave your tree in the alley for the garbage crew to find eventually, there’s a much more environmentally friendly way to bid farewell to the holiday season. The city has announced details of its 2026 Christmas tree recycling program, which collects trees for composting from January 3–17, 2026, in parks across the city. Before you lug your tree to a recycling site, you'll need to ensure that it's stripped of any ornaments, tinsel, lights or other decorations—only bare trees are accepted for recycling. You'll be able to drop off your tree whenever participating parks are open to the public (check the Chicago Park District website for hours). RECOMMENDED: The most festive holiday restaurants in America Once collected, the trees are converted into mulch, which Chicagoans can pick up for free on a first come, first served basis. Residents can snag a bag at six specific locations: North Park Village, Warren Park, Margate Park, Lincoln Park, Mt. Greenwood Park and the Forestry Site. Below is the full list of parks where you can drop off your Christmas tree. Last year, Chicagoans recycled more than 22,000 trees—here’s to breaking that record this season! City of Chicago holiday tree recycling locations (alphabetical order):  Bess