Shannon Shreibak is the Things To Do Editor at Time Out Chicago. A proud Midwesterner—a "Region Rat," if you want to get painfully specific—they bring a deep love for hyper-local culture and a decade of experience in Chicago’s events and music scenes.

Before joining Time Out, Shannon worked behind the scenes at cultural landmarks like Metro Chicago, the Adler Planetarium, Empty Bottle, and Thalia Hall. They’ve also written about arts, culture, and music for outlets like Chicago Reader, Bandcamp, and TASTE, with a focus on uncovering the people, places, and moments that shape city life. In addition to editorial work, Shannon is a fiction writer and occasional performer at live storytelling shows around Chicago.

When they’re not attending events or writing about them, Shannon is usually riding their highlighter-yellow bike around town, toiling over a new sewing project, or posting about their cat on Instagram.

Got an event tip or a story idea? Reach out at [email protected].

Shannon Shreibak

Shannon Shreibak

Things to Do Editor, Chicago

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Articles (56)

The best things to do in Chicago this week

The best things to do in Chicago this week

Last updated January 16, 2026: Whether you’re diving into the Chicago Polar Plunge 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
The best things to do in Chicago this weekend

The best things to do in Chicago this weekend

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 14, 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 a massive vintage festival taking over the DuPage County Fairgrounds (which is accessible via both car and Metra), pilates at the iconic Auditorium and the second weekend of Tomorrow Never Knows 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
The best things to do during winter in Chicago

The best things to do during winter in Chicago

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
The best March 2026 events in Chicago

The best March 2026 events in Chicago

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 flower shows at the Chicago Botanic Garden and Garfield Park Conservatory, sip wine after-hours at the Museum of Science and Industry 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
The best February 2026 events in Chicago

The best February 2026 events in Chicago

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
The best free museum days in Chicago

The best free museum days 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
The best December 2026 events in Chicago

The best December 2026 events in Chicago

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 glĂŒhwein 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
The best November 2026 events in Chicago

The best November 2026 events in Chicago

Welcome to November in Chicago! You've got about two weeks of breathing room after Halloween before holiday events begin in earnest, from twinkling Christmas lights displays to the first days of Christkindlmarket in Daley Plaza and Wrigleyville. And of course, don't forget about Thanksgiving in Chicago. Hoping to avoid the holidays altogether? Take a spin on the Maggie Daley Ice Skating Ribbon or huddle away from the wintry weather at one of many Chicago museums as temperatures start to plummet. Say goodbye to fall in Chicago with the help of our list of the best things to do in Chicago this November. RECOMMENDED: Check out our 2026 Chicago events calendar
The best things to do in Chinatown, Chicago

The best things to do in Chinatown, Chicago

Many people head to Chinatown for its wealth of excellent restaurants, but the neighborhood offers much more than incredible food. You can spend half a day exploring the various shops in Chinatown Square or learning about Chinese history and culture at one of the neighborhood's museums. The area is also home to one of the city’s most beautiful parks, which provides skyline views and is accessible by water taxi. And if you're lucky, you might even find a parade or celebration taking place during your visit. So don’t come solely for the dim sum (even though it's pretty amazing as well), here are some of the best things to do in Chinatown. RECOMMENDED: Our complete guide to Chinatown
The best dim sum restaurants in Chicago

The best dim sum restaurants in Chicago

When the weekend rolls around, the best dim sum restaurants in Chicago buzz with energy. Families and friends come together to feast on dumplings and bite-sized Chinese morsels, often tucked inside steamer baskets and served alongside tea. It's an ideal choice for those who want to try a bit of everything—from shrimp dumplings and chicken feet to sesame balls and egg yolk buns. Are you drooling yet? Some of the top Chinatown restaurants specialize in traditional dim sum service, while other Chinese restaurants feature creative spins on the time-honored culinary practice. We've compiled a list of all of the best of Chi dim, and have a diverse set of locations sprinkled about the city. Find a way to get to all of them if you can. RECOMMENDED: Discover the best things to do in Chicago's Chinatown
The best Midwest winter getaways for families

The best Midwest winter getaways for families

Who says you need to escape the Midwest in winter? Any Chicagoan knows the dark months can be tough, but those who thrive don’t begrudgingly tolerate the winter—we embrace it. Within a few hours’ drive of Chicago, you’ll find towns, resorts and state parks with exciting, snow-forward outdoor adventures for the whole family like dog sledding, tubing and snowboarding, plus plenty of cozy indoor spots to lean into our Midwestern version hygge. Whether you and your family love to brave the elements or spend afternoons at bookstores, coffee shops and breweries, put on your layers, grab your snowshoes and get ready for fun. Here are the best winter getaways from Chicago. RECOMMENDED: The best day trips from Chicago
Dennis Scott is the man who makes the Music Box sing

Dennis Scott is the man who makes the Music Box sing

Photograph: Gracie Hammond for Time Out When most people think of an organ, they picture pews and hymnals, not popcorn and previews. But when Dennis Scott settles in at the console of the near-century-old organ inside the Music Box Theatre, the sound is anything but solemn. Dressed in a dapper suit, a grin sweeping across his face, Scott coaxes joy out of those ancient pipes like he’s convincing the instrument to laugh again. Scott first sat down at the organ housed in the Music Box, a vintage cinema in Chicago’s quaint Southport Corridor, in 1992. A few years later, the demands of his day job forced him to step away—a practical choice that felt, even then, like walking offstage mid-song. He returned in 2009, sliding back into the bench as if no time had passed, and by 2011 he’d launched a monthly silent film residency that made century-old reels feel alive again. These days, he’s not just the Music Box’s house organist but the official accompanist for The International Buster Keaton Society, performing everywhere from the University of Chicago’s Rockefeller Chapel to the Orpheum Theater in his hometown of Tulsa, Oklahoma—still finding new ways to make silence sing. And yet, for all his travels, it’s December that brings him home again. Each year, Scott trades in his silent films for something decidedly louder: the annual Music Box Christmas Sing-A-Long & Double Feature. Now in its 42nd year, the event has become something close to a civic ritual. For nearly three weeks, car

Listings and reviews (35)

Show & Tell for Grown-Ups

Show & Tell for Grown-Ups

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.
Pokémon Fossil Museum

Pokémon Fossil Museum

Whether you’re parenting a pint-sized PokĂ©mon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the PokĂ©mon 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 PokĂ©mon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect PokĂ©mon models, real fossil excavation tools and immersive soundscapes throughout.
Yoonshin Park: Prompt and Prompted

Yoonshin Park: Prompt and Prompted

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.
Crafting Character: The Costumes of Paul Tazewell

Crafting Character: The Costumes of Paul Tazewell

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.
I AM WILD: A Charley Harper Exhibit

I AM WILD: A Charley Harper Exhibit

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.
A Tale of Today Presents Brendan Fernandes: In the Round

A Tale of Today Presents Brendan Fernandes: In the Round

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.
Korean National Treasures: 2,000 Years of Art

Korean National Treasures: 2,000 Years of Art

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.
If Emmett Till Lived: Freedom on American Ground

If Emmett Till Lived: Freedom on American Ground

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.
MoCP at Fifty: Collecting Through the Decades

MoCP at Fifty: Collecting Through the Decades

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.
Dancing the Revolution

Dancing the Revolution

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.
Drag Race: The Experience

Drag Race: The Experience

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
Amadeus at Steppenwolf

Amadeus at Steppenwolf

5 out of 5 stars
In Peter Shaffer’s Amadeus, genius is not just a blessing: It’s a declaration of war. Composer Antonio Salieri sees himself as one of its principal casualties. Once the darling of the 18th-century Viennese court, he watches in mounting horror as “the creature”—his term for the rising musical prodigy Wolfgang Amadeus Mozart—launches an artistic takeover that endangers not just Salieri’s career but his very conception of himself. The scaffolding of his principles collapses beneath his suspicion that God has chosen someone else above him, and his devotion rots into destruction. Amadeus | Photograph: Courtesy Michael Brosilow Salieri never leaves the stage. Recounting his venomous rivalry from the safety of his deathbed, he is both Amadeus’s antagonist and its narrator, and his voice is the lens that refracts the entire story. Once he had offered his life in monastic devotion to music and to God; now he confesses how swiftly he turned away from both when Mozart revealed what true genius sounds like. In a lesser actor’s hands the role might wear thin, but Ian Barford, seasoned in Steppenwolf cynics since 2017’s Linda Vista, is magnetic. Salieri insists on being the omniscient puppeteer behind Mozart’s downfall, yet the audience can’t quite believe him. His envy is so vast it becomes its own orbiting body, circling a sun named Mozart. That sun is played by David Darrow, whose Mozart radiates an irresistible, maddening charm. Darrow leans into the character’s impish, sophomoric hum

News (96)

How to watch the Bears vs. Rams this Sunday: TV schedule, streaming and Chicago watch parties

How to watch the Bears vs. Rams this Sunday: TV schedule, streaming and Chicago watch parties

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
Is this Chicago Victorian home really one of the “ugliest in America”? HGTV thinks so.

Is this Chicago Victorian home really one of the “ugliest in America”? HGTV thinks so.

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 five best things to do in Chicago on Martin Luther King Jr. Day

The five best things to do in Chicago on Martin Luther King Jr. Day

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
Chicago sweeps the Tripadvisor Awards, clinching top U.S. destination and two other prestigious titles

Chicago sweeps the Tripadvisor Awards, clinching top U.S. destination and two other prestigious titles

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.
This is the No. 1 thing to do during winter in Chicago, according to Time Out

This is the No. 1 thing to do during winter in Chicago, according to Time Out

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
This is the No. 1 winter getaway for Chicagoland families, according to Time Out

This is the No. 1 winter getaway for Chicagoland families, according to Time Out

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
Chicago’s best winter fest is finally here. Here’s the scoop on Tomorrow Never Knows.

Chicago’s best winter fest is finally here. Here’s the scoop on Tomorrow Never Knows.

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
Chicago has a new No. 1 bookstore, according to Time Out

Chicago has a new No. 1 bookstore, according to Time Out

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
Chicago Christmas tree recycling 2026: Dates, locations and map

Chicago Christmas tree recycling 2026: Dates, locations and map

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
10 art exhibitions in Chicago to look forward to in 2026

10 art exhibitions in Chicago to look forward to in 2026

Chicago’s art scene has never been accused of subtlety. One minute you’re contemplating Matisse’s cut-paper reveries, the next you’re comparing PokĂ©mon fossils. It’s a city that believes more is more—and 2026 is shaping up to be no exception, with a slate of major exhibitions that span centuries, continents and emotional registers. Whether you’re a devoted art hound or someone who only remembers that museums exist when the weather turns particularly cruel, there’s something for nearly every aesthetic inclination in the year ahead. These are the 10 Chicago art exhibitions we’re already making plans to visit in 2026. RECOMMENDED: 11 things to look forward to in Chicago in 2026 Henri Matisse, Printed by Edmond Vairel, Published by TĂ©riade for Éditions Verve. Horse, Rider, and Clown from Jazz, 1947. Simeon B. Williams Fund. © 2025 Succession H. Matisse / Artists Rights Society (ARS), New York. Matisse’s Jazz: Rhythms in ColorThe Art Institute of Chicago, Mar 7–Jun 1, 2026 Bedridden and unable to paint in the 1940s, famed French artist Henri Matisse turned to a new, more accessible medium: cut paper. Drawing from memories of circuses, world travel, folktales and Parisian music halls, he created a series of 20 maquettes that will be on view. In 1947, these vibrant compositions were reproduced using pochoir (stencil) techniques and paired with Matisse’s own writing to create the unbound book Jazz. This exhibition marks the first time Matisse’s Jazz will be shown in its entirety si
11 things to look forward to in Chicago in 2026

11 things to look forward to in Chicago in 2026

As 2025 winds down, it’s only natural to start peering into the future, preferably with a calendar in one hand and a mild sense of optimism in the other. Chicago, never a city to sit idle, has a full slate of big ideas queued up for the year ahead—from monumental civic projects to long-teased cultural openings that promise to give us something new to argue about, line up for or Instagram excessively. So don’t let the winter blues—or your group chat—convince you that nothing ever happens here. While delays can (and invariably do) happen, the next 12 months are shaping up to deliver plenty of bucket list–worthy moments. Without further ado, here are the things we’re most looking forward to in Chicago in 2026. RECOMMENDED: The best New Year’s Eve events and parties in Chicago to ring in 2026 Photograph: The Obama FoundationA rendering of the Obama Presidential Center. Celebrating the opening of the Obama Presidential Center Opening in June 2026, the Obama Presidential Center will redefine the concept of a presidential library. Rooted in President Obama’s history as a community organizer in Chicago, the Hyde Park campus is designed as a civic-minded hub focused on public engagement and future leadership. The sprawling complex will include a new Chicago Public Library branch, a community garden, a basketball court, a recording studio, classrooms and more. Reviving ancient PokĂ©mon at the Field Museum Whether you’re parenting a pint-sized PokĂ©mon devotee or a nostalgic millennial
This national park is just a one-hour train ride from Chicago—and it’s perfect for a winter day trip

This national park is just a one-hour train ride from Chicago—and it’s perfect for a winter day trip

Growing up in the northwest corner of Indiana—colloquially known as “The Region”—I learned early how to make the best of the Midwest’s frigid temperatures and blanketings of snow. One of the perks of a childhood spent in this sleepy pocket of the state was regular trips to Indiana Dunes National Park, which stretches across 15 miles of Lake Michigan shoreline. Known for its rolling sand knolls, expansive beaches and diverse flora, the park slips easily into winter wonderland mode by year’s end. Lucky for Chicagoans, the Indiana Dunes are remarkably easy to reach by car or train. It’s just a one-hour ride on the South Shore Line or a quick drive along I-90/94. With winter still firmly in residence, there’s no better time to climb snow-dusted dunes and snap photos of Chicago’s icy skyline from across a frozen Lake Michigan. RECOMMENDED: The 22 most epic Metra day trips from Chicago Photograph: Shannon Shreibak If you’re taking the South Shore Line, there are two prime ways to access the Indiana Dunes—one of which is the Miller Beach stop, stationed in a historic lakefront neighborhood in Gary, Indiana. The area offers plenty to explore, from the Japanese bridge at Patterson Island to the black oak-packed savannah of Miller Woods and a smattering of midcentury architecture. Literature lovers can hike the Nelson Algren & Simone de Beauvoir Trail, which begins just steps from the house where the two writers carried on their affair—and where Algren penned The Man with the Golden