Shannon Shreibak

Last updated February 9, 2026: Whether you’re booed up this Valentine's Day weekend or hitting the town solo, there’s plenty to look forward to. The week's lineup features everything from the kickoff of Garfield Park Conservatory's annual spring flower show and the start of Chicago Theatre Week to a Valentine's Day party specifically for puppies. Even on a budget, you can take advantage of free admission days at several Chicago institutions or catch a free show at Empty Bottle. 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 February 2026

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

Chicago is undoubtedly a city of romance. Across the Windy City, our charming tree-lined parks, sultry speakeasies and staycation-worthy historic hotels seem to exist solely for lovers in search of things to do together. Whether your ideal date night involves wining and dining at one of Chicago’s most romantic restaurants or cruising down the river in a floating hot tub boat, these romantic activities for couples will help keep the sparks flying. RECOMMENDED: Find the best unique date ideas in Chicago

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 February 4, 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 Auto Show, the final days of Chicago Restaurant Week and the kickoff of Chicago Theatre Week. 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

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.

Last updated February 3, 2026: As it turns out, some of the best things in life—or at least, some of the best things to do in Chicago—are free. There are plenty of free ways to spend your time over the next few weeks, including ice skating and a visiting some of the city's world-class museums. Plus, don't miss out on gallery shows, concerts and other recurring events that won't cost you a dime. Ready to save some money without sacrificing any fun? Check out more of the best free things to do in Chicago this month. RECOMMENDED: The best free museum days in Chicago RECOMMENDED: The best cheap eats in Chicago

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 February 3, 2026: 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

Get excited, Chicagoans, because spring in Chicago is officially here. (Later, snow!) The warmer temps are perfect for hiking near Chicago or taking a day trip to enjoy a quick getaway but there’ll be plenty of fun in the city, too. For movie lovers, there's the return of Doc10 Fest. Art buffs can get their fill at the annual EXPO Chicago or The Art Institute of Chicago's one-of-a-kind Matisse exhibition. There's also plenty to do outside, including the city's much-anticipated cherry blossom viewing. So celebrate the spring season—and all the new beginnings that go along with it—with our list of the best things to do in Chicago this April. RECOMMENDED: Events calendar for Chicago in 2026

We’ll be honest: January is not exactly Chicago’s finest month. But before you start to dwell on the prospect of snow, cold and seemingly endless winter, allow us to point out some of the best ways to kick off the first few weeks of 2026. Start by catching the final days of Christmas lights in Chicago (they offer a nice excuse to take a walk outside, even when the holidays have passed) and get some fresh winter air when you take a spin around the best ice skating rinks the city has to offer. Prefer to stay inside? Tour new exhibits at Chicago museums—many of which offer free days over the next few months—or check out some of the best things to do indoors, including rock climbing, bowling and soul-warming spa days. Make a resolution to start the year on the right foot with the help of our guide to the best things to do in Chicago this January. RECOMMENDED: Events calendar for Chicago in 2026

The arrival of December sends the holiday season into full swing—prepare yourself for a jam-packed roster of glittering Christmas lights, festive holiday pop-ups and plenty of glühwein to be sipped at Christkindlmarket locations in both Daley Plaza and Aurora. As the month draws to a close, bid adieu to 2024 at New Year's Eve events and parties happening at Chicago hotels, clubs and other hotspots, where you'll find Champagne towers and other special ways to welcome 2025 in style. So make the most of the final month of the year with our guide to the best events in Chicago this December. RECOMMENDED: Check out our 2026 Chicago events calendar

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

The Savannah Bananas, a theatrical exhibition baseball team taking the world by storm, are swinging through Chicago next year alongside their Banana Ball Championship League brethren. After selling out two back-to-back games at Comiskey last year—or, if we must, Rate Field—the purveyors of “Banana Ball” are returning in 2026 for a three-night residency at Wrigley Field.

What do we talk about when we talk about the weather? We talk about the planet’s slow boil: the seasons that change without our consent, the arrow of time that pierces our lives regardless of our armors. Medical researcher John and his adult daughter Caitlyn talk about the weather constantly in In Birds of North America; nearly every scene of Anna Ouyang Moench’s one-act play touches on the subject. Set in suburban Maryland and unfolding over a decade, the play tracks their relationship like an ornithologist watching the sky: full of hope, yet braced for disappointment. Species of bird appear late, vanish early or never arrive at all. Their altered patterns mirror a filial relationship that keeps missing its own landing, circling ground without touching down. Birds of North America | Photograph: Evan Hanover, Courtesy A Red Orchid Theatre The play opens at the dawn of the Iraq War—a moral backdrop that weighs heavily on John, a lifelong liberal, eco-warrior and former doctor who sacrificed professional success to pursue a cure for Dengue fever. He catalogs the world with scientific precision, logging birds in his red palm-sized notebook while flattening human emotion with the same rigor. (He speaks of Caitlyn’s miscarriage as casually as he might note a species count in decline.) Caitlyn, meanwhile, works as a copy editor for a right-wing news site, a compromise she frames as a temporary shelter from the torment of capitalism rather than a personal conviction. She dreams of

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.

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.

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.

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.

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.

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.

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.

Sure, a picture says a thousand words, but a photo booth strip says something closer to, “We were here, and we were briefly this version of ourselves.” It’s a fleeting moment, a tiny diary entry, something that can only happen behind the curtain of a booth. The Strip Club trades in this kind of sentimental magic. Located at 1702 North Damen Avenue in the heart of Wicker Park, the new spot houses 10 analog and digital photo booths (with one more on the way), each offering a slightly different personality. One prints a single image framed by a heart-shaped doily. Another delivers three strips of dreamy black-and-white photos, ready to be divided among friends like rations after a long night out. The Strip Club is also home to the oldest operating photo booth available to the public: a pill-shaped behemoth that goes by the name “Lady.” Each strip costs $7, and yes, the machines accept credit cards—nostalgia, modernized. Praise be, The Strip Club isn’t the product of some venture capital-backed brainstorm session. It’s the latest project from husband-and-wife team Anthony and Andrea Vizzari, whose company A&A Studios supplies photo booths to many of Chicago’s favorite bars and music venues (Empty Bottle, Cafe Mustache, Schubas Tavern and then some), as well as spots across the country.   Photograph: Shannon Shreibak   The Vizzaris’ photo booth origin story dates back to 2007, when Anthony began tinkering with used machines in the garage of their Logan Square home. For him, it w

At Time Out, we refresh our rankings often, because loving Chicago doesn’t mean staying loyal to the same old favorites out of habit. This month, we revisited our guide to the city’s top 24 florists and decided it was time for a gentle but decisive shake-up. Along with adding a few new flower shops that are keeping Chicago colorful, fragrant and on its aesthetic A-game, we reshuffled the rankings to reflect recent developments and the simple truth that cities—like tastes, hairstyles and what we’re willing to pay for a bouquet—are always changing. As a result of our latest reporting, Humboldt Park's Nerine has officially claimed the number one spot as the best florist in Chicago. RECOMMENDED: How to celebrate Valentine’s Day in Chicago Photograph: Steven Piper, Courtesy of Nerine Co-founders Liz Topp and Sinéad Cleary launched Nerine to celebrate the meeting point of fresh blooms and sculptural artistry. Every bouquet captures a fleeting seasonal mood and an unmistakable creative point of view—the floral equivalent of walking into a room and immediately trusting the host’s taste in music. Since opening their physical shop on Division Street in early 2025, they’ve welcomed flower lovers into their world with curated arrangements and hands-on workshops that make you briefly consider a career change. In determining our rankings, we weighed floral adventurousness and shop ambiance against a more elusive metric: the thrill of discovering you’ve walked into a place that also sells

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