Shannon Shreibak

New Year's Eve is right around the corner and if you still haven't made plans yet, we’ve got some ideas about how to send 2025 off in style. Whether you prefer to dress up and twirl among thousands of revelers at fancy hotel soirees, watch the fireworks show from a rooftop or keep things casual at a neighborhood bar, there's no shortage of options for a good time. So give a hearty welcome to 2026 with Chicago's best New Year’s Eve events and parties. RECOMMENDED: Our complete guide to New Year's Eve in Chicago

Photograph: Gracie Hammond for Time OutSimone Mitchell-Peterson “At the end of the day, we come into this world with nothing and we leave this world with nothing,” Simone Mitchell-Peterson tells me. She isn’t speaking mournfully—just matter-of-factly, pointing out the parameters we are all given. Within that narrow window between the first nothing and the last, Mitchell-Peterson says, we’re offered a daily invitation: “I’ve learned about the fortitude in choosing joy each day—because I really believe that’s a choice. And if you can’t choose it for yourself, then let somebody help you along the way.” For 21 years, Mitchell-Peterson has been helping older adults choose joy as the CEO of the Chicago chapter of Little Brothers – Friends of the Elderly, a national network of nonprofits that provides companionship and care for the aging community. Through food deliveries, visiting programs and summer getaways at Audrey’s House—the organization’s year-round community center in the western Chicago suburbs in Batavia, IL—Little Brothers supports roughly 1,000 adults aged 70 and over throughout Chicagoland. While Mitchell-Peterson prioritizes celebration year-round—birthday parties, themed events and personalized gifts for older adults—the holiday season holds a special kind of excitement for both her and the community she serves. With the help of volunteers and donors, Little Brothers hosts family-style holiday gatherings complete with music, dancing and, of course, a hearty shared m

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

As we approach the end of the year, it’s only polite to glance back at 2025 and acknowledge everything Chicago—and the world—asked of us. And it asked a lot. This was the year we were reminded that we really do rely on our neighbors, our block and the merciful stranger who lets us merge onto Lake Shore Drive during rush hour. We were called to show up, pitch in and care about the corners of the city that are neglected far too often. But 2025 wasn’t all grit and civic fortitude. It was also delicious, surprising and sometimes downright delightful. New restaurants and bars opened and fresh festivals and exhibitions popped up the way the Red Line does on a good day—right on time and deeply appreciated. Through it all, the Time Out Chicago editors kept eating, strolling, admiring and occasionally marveling—because that is, after all, the job. The picks that follow are the ones that stayed with us—meals we’re still thinking about, experiences we can’t stop recommending and moments that reminded us why living in this city is worth the rent, weather and the bureaucratic headaches. So, without further ado, here are the best things we saw, ate and did in 2025.

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 December 3, 2025: With Chicago officially snow-capped and steeped in festive energy, now is the time to fully embrace the season. Carve out some time to gawk at the many holiday light displays around town, or rent a pair of skates for an afternoon at the best ice skating rinks in Chicago. Ready to knock out some holiday shopping? From Maker’s markets to in-store events, there are plenty of ways to shop small this weekend—we even made you a handy guide to our top five independent shops for unique holiday gifts. Whether you’re looking for the best events in Chicago during the holiday, planning a spontaneous night on the town or just exploring what’s new around the city, there’s no shortage of incredible things to do this holiday weekend. 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

Between the amazing restaurants to try, swankiest bars to visit and best things to do, having a good time in Chicago can be expensive. However, there are still plenty of options for fun on a budget. Chicagoans have access to affordable museums around the city, theater shows that don't break the bank and even a cat cafe. Here are some of the best cheap things to do in Chicago for under $20. And for even more cost-effective options, check out the best free things to do in Chicago. RECOMMENDED: The best cheap eats in Chicago

Last updated December 1, 2025: 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 handful of winter markets. 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 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) Lincoln Park Zoo – Historic zoo and host to one of the largest displays of holiday lights within city limits (Free) Willis Tower Skydeck and “The Ledge” – Enjoy sky-high views and step onto glass ledges above the city ($36–$45) Last updated December 1, 2025: Chicago has shifted into full winter wonderland mode, offering a wealth of things to see and do this December. Whether you're interested in exploring iconic sights, diving into culture or embracing the holiday energy, the city has you covered. The festive lineup includes marveling at massive ligh

Last updated December 1, 2025: Whether you’re looking for the best events in Chicago during the holiday season, planning a spontaneous night on the town or just exploring what’s new around the city, there’s no shortage of incredible things to do this week. Chicago is fully embracing the festive feels this week with events like the CTA Holiday Train and Bus, Navy Pier's Cheer at the Pier extravaganza and the oh-so-Instagrammable ZooLights at Lincoln Park Zoo. Ready to knock out some holiday shopping? One of a Kind Holiday Show returns this weekend with wares from over 600 makers—better yet, a portion of proceeds from each ticket sold will benefit Ann & Robert H. Lurie Children’s Hospital of Chicago. RECOMMENDED: Discover the best things to do in Chicago in December 2025

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 2025 Chicago events calendar

Last updated November 21, 2025: Christmas shopping can be stressful if you’re searching the web for the best deals or braving the crowds at a big box store, but it’s much more fun if you go somewhere that really embraces the spirit of the season. Christmas in Chicago is a magical time filled with incredible holiday light displays and over-the-top pop-up bars—so it’s no surprise there are plenty of equally charming shopping destinations throughout the city, from festive seasonal markets to stores that go all-out with their decorating. Find something fun for everyone on your list by hitting up the best Christmas stores in Chicago. RECOMMENDED: Your complete guide to Christmas in Chicago

Visiting “The Land of Oz: Beyond the Page” at the Gold Coast’s Driehaus Museum feels a bit like opening a very elegant jewelry box: beautifully crafted, lovingly arranged and also...surprisingly compact. Tucked away into two rooms on the museum’s top floor, the film-inspired exhibit offers a curated peek behind the yellow brick road—costumes, concept art, early editions of L. Frank Baum’s original book and just enough memorabilia to spark a pleasant jolt of nostalgia. The exhibit's highlights include a replica of Dorothy’s slippers—one of only 20 editions worldwide—and a collection of “movie edition” Wizard of Oz books adjusted to better match the silver-screen adaptation. In the end, the Driehaus Museum’s Wizard of Oz exhibit doesn’t attempt to sweep you away in a tornado of spectacle so much as hand you a small, neatly labeled basket of curiosities. Its strength lies in details—like early drafts of the film’s script and a replica of the Cowardly Lion’s courage medal, which was a departure from the book’s bottle of courage the character drank. It’s these little factoids that make the exhibit worth a visit. While the exhibition may leave devoted Oz scholars wanting more, it offers casual visitors a gentle, concentrated dose of nostalgia within the museum’s ornate surroundings. You may not walk out feeling as though you’ve traveled all the way to the Emerald City, but you will have enjoyed a tidy, thoughtfully assembled layover somewhere between fantasy and reality.

Do you like riding your bike? How about delicious Mexican food? Do you want to support local street vendors? If you’ve answered “yes” to all of the above, CyclingxSolidarity’s Street Vendor Bike Tour is the place to be. Organized in partnership with the Street Vendors Association of Chicago, the Bike Tour is designed to build community, one bike and meal at a time. The event will kick off with two stops in Pilsen during which CyclingxSolidarity will highlight its mutual aid efforts and partnerships with local organizations. The bike tour will then move westward toward Little Village, where cyclists will meet street vendors, hear their stories and enjoy delicious food at three different stops. The event is open to cyclists of all skill levels. “I want this tour to act as open arms to welcome people to Little Village and other communities where we have built bridges with local community organizations and introduce them to the people, places and food that make up these beautiful communities,” Rick Rosales, community organizer for CyclingxSolidarity says. “They need our support more than ever and for those of us that love to ride bikes, this seemed like a perfect opportunity.” Rosales hopes that this event will be the first of many Street Vendor Bike Tours. Learn more about CyclingxSolidarity’s mission here.

If Wes Anderson designed a cafe-meets-gift shop, it would probably look a lot like The Center of Order and Experimentation. Step inside and you're greeted by a velvet-upholstered counter, sticker-covered clipboards and sleek, futuristic-font signs declaring that the space is "not a cult." Cake-shaped candles, fluorescent tea boxes and handmade ceramics are artfully arranged on shelves and tables, every detail carefully curated. The space is often buzzing, especially during weekend micro-bakery pop-ups, watercolor workshops and other whimsical events.  

Inspired by the cultural resurgence of Mort Garson’s synth-powered album Mother Earth’s Plantasia, Empty Bottle Presents and Sacred Bones Records have been hosting an annual music festival celebrating plants and people who love them for nearly half a decade. Spread across two days, attendees can enjoy experimental music and on-site activations in the Garfield Park Conservatory's lush confines. This year's Plantasia lineup includes electronic music legend Suzanne Ciani, ambient juggernaut Tim Hecker, Pakistani composer Arooj Aftab and more.

The latest addition to the Salt Shed's sprawling grounds is a pinball palace owned by none other than Jim Zespy of Logan Arcade. Housing over 100 games, 8-bit purists, pinball wizards and casual gamers alike will all find fun ways to collect virtual prize tickets, which can be redeemed at a fully-stocked prize shop. Billed as an all-ages space by day and adult-centric playground—complete with jello shots—by night, there's something for everyone at Elston Electric.

What happens when a grift lands you smack dab in the center-court spotlight during the Chicago Bulls’ legendary 1996 reign? BULL, a two-act comedy following unathletic schemers Scott and Bryce, sets out to answer exactly that. As the duo navigates a grand con and the chaos of unexpected fame, they struggle to hold their friendship together—all against the backdrop of one of the most iconic eras in Chicago sports history.

When Pitchfork Music Festival announced its sudden sunset at the start of 2025, Chicago’s music scene collectively wondered how festival co-founder Mike Reed would fill the sonic void. Turns out, Reed had an ace up his sleeve: Sound & Gravity, a five-day music marathon featuring 48 performances across six venues in Bricktown and Avondale. Lineup highlights include Bill Callahan, Mdou Moctar and Mary Lattimore, with some special sets curated by Electrical Audio—the recording studio founded by the late Steve Albini. Read more about Sound & Gravity's inception here.

Wander into Carol's Pub on the second or fourth Tuesday of the month, and you might not recognize the iconic country dive. No cowboys downing High Life, no two-stepping in sight. Instead, you’ll find a rowdy crowd waving jello shots (proceeds benefit a rotating charity) and gleefully dabbing bingo cards with multicolored markers. Welcome to Cougar Bingo, hosted by comedian Brittny Congleton, who performs as the fabulous Aunt Nance. Throughout the night, Nance calls out bingo numbers with the flair of a tipsy Midwest aunt, mixing in musical interludes, sharp one-liners and the occasional George Michael reference.

Stationed on the first floor of the Chicago Cultural Center, Buddy is a one-stop shop for any locavore on the hunt for the perfect gift—whether for a friend or just yourself. The boutique features work from over 400 Chicagoland artists, with options ranging from ceramics and clothing to zines and more. Don't miss their rotating lineup of events, including the “Art 4 Sale” exhibition series, seasonal window installations on Randolph Street and monthly in-store happenings.    

The Midwest’s largest free outdoor literary festival returns this September for its 40th year. Book lovers can browse offerings from more than 150 booksellers and exhibitors, while six stages and over 200 presenters deliver programming for all ages. While the full lineup is still under wraps, this year's festival will be headlined by Sandra Cisneros—author of The House on Mango Street and recipient of the 2025 Harold Washington Literary Award.

This one’s for the birders out there! Stop by the Newberry Library this August and September for a free guided tour of "Winging It: A Brief History of Humanity's Relationship with Birds,” an exhibit exploring the cultural and environmental resilience of birds across eras and civilizations. The tour ends in one of the library’s cozy reading rooms, where you can chat about what you’ve learned or dive into everything else the Newberry has to offer. (Spoiler alert: it’s a lot.)

During the summer, spending more time indoors than absolutely necessary feels almost sacrilegious. The Music Box Theatre gets it—and fully embraces the season by inviting movie lovers into its charming outdoor garden. Grab a specialty cocktail (each one cleverly named after an iconic film) and settle in for a night of cinema under the stars. Highlights of this year’s lineup include The Texas Chainsaw Massacre (the 2003 remake, for the horror purists out there), Dirty Dancing and The Goonies.

Wrigleyville will play host to a very sweet debut next week: Chicago’s first-ever cookie market. The event is brought to life by Cookies for Kids’ Cancer, a nonprofit that raises funds for pediatric cancer research, and promises a fusion of holiday cheer and philanthropy. It’s the kind of sweet combination that feels festive, heartwarming and only slightly threatening to your waistband. On Sunday, December 14, Cookies for Kids’ Cancer will host the Chicago Cookie Market at the Christmas Club (3460 N Clark St). The event gathers 40 of the city’s top pastry chefs for a festive day of giving, featuring talent from national icons like Gale Gand and Mindy’s Bakery to local darlings Cafe Yaya and Loba Pastry. Guests will be able to taste-test confections and select two dozen hand-picked cookies to take home. “After participating in fundraisers supporting Cookies for Kids Cancer in NYC, I knew I needed to help expand their reach to my hometown Chicago,” Jenny McCoy, pastry chair of the event said. “It's not only a wonderful charity doing such great work, but one that pulls together my favorite community: professional and home bakers.” Proceeds from the event will benefit Cookies for Kids’ Cancer, a national nonprofit that supports over 40 leading pediatric oncology programs. Locally, this support includes the Ann & Robert H. Lurie Children’s Hospital of Chicago and the University of Chicago Comprehensive Cancer Center. Specifically, the funds raised will help cover the enrollment co

When praising Chicago, “waterfront destination” may not be the first phrase to roll off the tongue. Most of us reserve that for places where the water doesn’t freeze into an ominous sheet of ice by mid-December. Yet, against all odds, Chicago has landed itself among the nation’s top Christmas boating destinations. According to Boat Booker, an online platform for coordinating aquatic tours and trips, Chicago ranks among the nation's 10 best locales for a holiday excursion, making it the only Midwest city to seize the crown. Miami, unsurprisingly, received glowing praise thanks to its tropical spin on festive decor—think light-studded palm trees and massive metallic ornaments artfully arranged in fountains. Rounding out the ranking is New York City, Seattle, Santa Barbara and New Orleans. RECOMMENDED: These are the best spots to see dazzling holiday Christmas lights in Chicago right now “Winter turns Chicago into a sparkling holiday destination,” reads the Chicago section of Boat Booker’s ranking. “As the city embraces the season, its waterways provide the perfect backdrop for festive adventures, blending urban charm with holiday magic.” Among the myriad qualities that helped Chicago clinch its high ranking are the Riverwalk’s dazzling holiday lights, the skyscrapers shimmering off the water like they’re trying to out-glitter the season itself and, of course, Lake Michigan, loyally framing the whole dreamy scene. Feeling inspired to chart your own cold-weather, sea-adjacent adv

Chicago has been raking in the accolades this year, from being voted the best big city in the U.S. for the ninth consecutive year to being home to one of the coolest neighborhoods in the world, but we’re not done yet: our town was just named the 35th best city in the world by Resonance Consultancy’s 2026 World’s Best Cities ranking. This isn’t just a flattering opinion, though: Resonance Consultancy and Ipsos, a multinational market research and consulting firm, crunched a whole slew of numbers to inform this global ranking. To come up with the report, the agencies surveyed over 21,000 folks across 30 different countries to determine each city's Place Power™ Score, which takes note of three different categories: livability (i.e., walkability, access to green space, air quality, etc.), loveability (i.e., culture, dining, attractions, etc.) and prosperity (i.e., economic indicators of success). London tops the global list for the 11th year in a row and New York lands at number two, the best city in the U.S. In addition to New York and Chicago, three other U.S. cities broke the ranking’s top 50: Los Angeles (number 12), Miami (number 26) and San Francisco (number 28). "Few cities on the planet are firing on all cylinders like America’s great Midwest metropolis," reads the Chicago section of the report. "The city is leaner and more efficient than ever, boasting the second-highest number of Fortune 500 headquarters in the country, behind only New York." Among the standout qualitie

Long before NFL players boasted carefully curated media brands or overly choreographed end-zone dances, the 1985 Chicago Bears threw down the gauntlet: they recorded a full-blown rap song and music video they dubbed “The Super Bowl Shuffle.” Meant as a lighthearted charity project—and recorded seven weeks before clinching Super Bowl XX—the song became a subject of both scorn and celebration. With linemen rapping, receivers shimmying and a beat that has survived four decades of good-natured ribbing, the song became a cultural artifact as memorable as the Bears’ dominant Super Bowl run itself. When the 1985 Chicago Bears dropped “The Super Bowl Shuffle,” the timing was equal parts audacious and premature—the NFL playoffs had not even begun, and the team had just suffered a bitter loss to the Miami Dolphins the night before the song’s recording. Yet the mix of bravado, charity ambition and pure Chicago grit transformed the song and accompanying music video—recorded at none other than Lincoln Park nightclub Park West—into something that transcended football. That story is now retold in the new documentary The Shuffle, which premiered last week on HBO Max. RECOMMENDED: This study proves why Chicagoans should be grateful the Bears are leaving Soldier Field Photograph: Courtesy of HBO The Shuffle was directed by longtime football documentarian Jeff Cameron, whose previous works include Hard Knocks: Training Camp, a deep dive into the NFL’s grueling training camps, and Bye Bye Bar

Ask any so-called expert what children need these days and you’ll get the usual answers: less screen time, more structure, consistent bedtime—and, inevitably, therapy. But according to Enrico Hufana, there’s something else kids need: the feeling of dropping into a quarter-pipe with nothing but a wooden board and the wings of their own confidence beneath them. Hufana is the founder of Little Ripper Skateboarding, a fast-growing skate school that began as a few lessons in a city park and has since evolved into a community hub—offering group and private classes, year-round programming and serving as an official Chicago Public Schools after-school provider. It’s not just a place to learn how to shred; it’s a space where kids build confidence, make friends and discover what they’re capable of. This year, they further expanded their reach, deepening their engagement with the community through grassroots activism and new after-school programming initiatives. It’s a vision that mirrors the organization’s mission: to bring skateboarding to kids of all ages, genders, racial and socioeconomic backgrounds—uplifting them through camaraderie, sportsmanship and community. In a city where access often depends on zip code or income, Little Ripper offers a space where everyone starts from the same place: one foot on the board, one push forward and a community ready to help them cruising. Photograph: Ricardo Adame From skater, to skate dad, to teacher Hufana’s love for skating began the way m

Mark your calendars—and prepare to warm up with some expertly crafted bourbon cocktails. On Sunday, December 4, Time Out Market Chicago will host Battle of the Bartenders, an epic cocktail showdown powered by Bulleit Bourbon. Some of Chicago’s top bars—including The Press Room, Friends of Friends and Kashmir—will go head-to-head for the chance to have their signature bourbon creation crowned number one. RECOMMENDED: The 24 best Chicago bars—the essential spots, ranked The best part? You decide the winner. Attendees can sample each bar’s cocktail, then cast their vote by dropping a gold coin (received at check-in along with drink tickets) into a ballot box of their favorite. The bartender and restaurant with the most votes will take home the coveted title of Top Bartender, plus a trophy, cash prize, a Time Out feature and, of course, bragging rights. Grab your friends and settle in for an afternoon of standout drinks, good vibes and maybe even the discovery of your next favorite cocktail. Battle of the Bartenders is a 21+ event. Tickets are $25 and can be purchased here.

Our 2025 reading list just got significantly longer, courtesy of Chicago’s literary experts. Every year since 1999, the librarians at the Chicago Public Library (CPL) have sifted through a heap of the year’s most exciting new releases to curate their definitive Best Books of the Year ranking. The result is a highly selective and essential cultural syllabus that immediately places you on the city’s literary cutting edge. The lists span three main categories—kids, teens and adults—that cover a swath of genres ranging from memoir and manga to sci-fi and books in Spanish. All titles are available through the library’s catalog, with many offered as e-books, audiobooks and accessible editions. These titles are already flying off the shelves, so place those holds now or pick up a copy of your own from one of Chicago's many bookstores. RECOMMENDED: The best bookstores in Chicago for new and used books Here are some of the best books of 2025 according to the Chicago Public Library: 10 best books for adults Black in Blues: How a Color Tells the Story of My People by Imani PerryThe Buffalo Hunter Hunter by Stephen Graham JonesFlashlight by Susan ChoiFlesh by David SzalayA Flower Traveled in My Blood by Haley Cohen GillilandIs a River Alive? by Robert MacfarlaneA Marriage at Sea by Sophie ElmhirstMother Mary Comes to Me by Arundhati RoyWild Dark Shore by Charlotte McConaghyWoodworking by Emily St. James 10 best fiction books for teens All the Noise at Once by Davis, DeAndraAnd the River

This Thursday, runners will embark on Turkey Trot races and families across the country will gather ’round a table for Thanksgiving dinner. But before those festivities unfold, the Chicago Thanksgiving Parade will step off in downtown Chicago. The 91st edition of the annual tradition will see the return of giant festive floats and helium balloons, including characters like Garfield, Rudolph and the Grinch, as well as marching bands from local high schools, cultural performance troupes, equestrian units and more. This year’s parade will feature special hosts and performers, including 2025 Miss Illinois Nitsaniyah Fitch, Miss Illinois’ Teen Lillie Brown, Marist High School Chicago Marching Band and some special guests from Mexico: Titanes Banda de Marcha and Venados Banda de Marcha. The broadcast will be hosted by Rock 95.5 personalities Maria Palmer and Maris. Here’s everything you need to know. RECOMMENDED: Discover the best things to do on Thanksgiving in Chicago What time is the Chicago Thanksgiving Parade? The parade is scheduled to kick off at 8am and run until 11am. What is the parade route? The procession will start at Ida B. Wells Drive and makes its way north on State Street, ending at Randolph Street. Is the Chicago Thanksgiving Parade free? Yes, the parade is free to attend and watch. Where is the best place to watch the Thanksgiving Parade in Chicago? The best spots to catch the action will be along the east and west ends of State Street. You can also purchase a VI

Chicagoans, we’re almost there! Thanksgiving is a mere few days away, which means it’s time to start hammering out those dreaded travel plans. Whether you’re flying out of town to visit friends and family or opting to drive to your holiday destination, Tuesday and Wednesday are expected to be some of the busiest travel days of the year, so you’ll want to plan accordingly. Compounding the holiday travel stress, AAA (the American Automobile Association) estimates that 81.8 million people will be traveling between Tuesday, November 25, and Monday, December 1—a 1.6 million leap from last year’s estimate. With that in mind, we did some research to figure out what the best time to embark on your journey is. What is the weather forecast for this Thanksgiving weekend in Chicago? It’s time to bust out the winter weather gear: After a week of above-average temperatures, Chicago is bracing for a sweeping cold front this Thanksgiving. NBC 5 estimates that temperatures on Thanksgiving and Black Friday will hover around the low-30s.  Chicago could experience polar vortex-esque conditions on or around Thanksgiving day. According to the National Weather Service’s Climate Prediction Center, “the combined effects from the current La Nina, the Madden-Julian Oscillation, and potential for a rare November Sudden Stratospheric Warming event may usher in a significant pattern change later in the month and into early December.”  To top it off, there’s a chance Chicago could be blanketed by snow by

Holiday shopping is supposed to be joyful in the same way that assembling Ikea furniture is supposed to be quick and easy: theoretically true, but rarely confirmed in practice. The pressure to find the perfect gift can drive even the most thoughtful person to doomscrolling gift roundups at 1am, convinced that nothing less than a hand-carved, ethically sourced heirloom will properly convey affection. Add in cryptic shipping deadlines and a litany of discount windows and suddenly buying presents feels less like an act of endearment and more like an endurance sport. This guide aims to simplify your holiday shopping while supporting stores within Chicagoans’ reach (and most of them offer online options, too). Because shopping local shouldn’t feel like homework; it should feel like finding a treasure you didn’t know you needed, offered by someone who is genuinely glad you walked through their door. RECOMMENDED: The 13 best Christmas stores in Chicago Photograph: Courtesy of The Center of Order and Experimentation The Center of Order and Experimentation 1727 W Grand Ave If Wes Anderson designed a cafe-meets-gift shop, it would probably look a lot like the Center of Order and Experimentation. Step inside and you’re greeted by a velvet-upholstered counter, sticker-covered clipboards and sleek, futuristic-font signs declaring the space is “not a cult.” Along with niche items—like cake-shaped candles, fluorescent tea boxes and handmade ceramics from local makers—COE is hosting a slew

Spin around, pick a direction and walk a few blocks down nearly any residential street in Chicago—you’ll probably stumble into a neighborhood tavern. They’re as much a part of the city’s landscape as the two-flats and bungalows, tucked beneath apartments or wedged between laundromats and taquerias. Step inside one of these neighborhood watering holes, and you’ll find the city distilled: old men arguing in vain about the Bears’ capacity to win any title worth a damn, a jukebox lodged in the liminal sonic space between Sinatra and Styx, and a bartender who’s been pouring drinks and stoking neighborhood gossip longer than most alderpersons have held office. These neighborhood bars are more than places to drink; they’re the city’s unofficial community centers, meeting houses and confessional booths—sometimes all before noon. But what once felt like an infinite supply of corner taps is quietly thinning out. Chicago’s taverns have been on the endangered-species list since the ’90s, victims of the Daleys’ “vote-dry” crusades, liquor-license moratoriums and a nagging capitalist impulse to make nightlife a little more like a River North craft cocktail circus and a little less like your cool aunt’s basement. Still, some of these places endure—dim rooms sprawled across street corners, where the bartender knows your name, your order and your love-to-loss ratio. They’re the places that make Chicago Chicago: where the city’s lines blur for a while and you remember how easy it is to become

The holliest, jolliest time of year is right around the corner, bringing with it a beloved Chicago commuter tradition: hopping aboard a train or bus festooned with twinkling lights, commandeered by Santa and his elves and blaring holiday tunes at top volume. That’s right: the Chicago Transit Authority (CTA) has finally announced the schedules for its Holiday Train and Holiday Bus, revealing when you can expect to see Santa making pre-Christmas Eve journeys through the city. The CTA Holiday Train will begin running on Friday, November 28, with trips scheduled on every CTA line throughout November and December as part of regular service. As usual, the six-car train will be headlined by an open-air platform hosting Santa and his crew of reindeer, as well as LED signs, colorful interior decorations and more lights than ever before. Photos with Santa have also returned, with designated photo op dates for both the Holiday Train and Bus. Photos will be taken by a CTA employee using your device, so free up some extra storage space for the occasion.  RECOMMENDED: These are the best spots to see dazzling holiday Christmas lights in Chicago right now Photograph: Courtesy Chicago Transit Authority If you prefer to experience holiday cheer at street level, you’ll be happy to learn that the CTA Holiday Bus will make an appearance on a whopping 19 routes throughout the city this year. This year’s bus will be adorned by a jovial wrap featuring Chicago landmarks, nods to Christkindlmarket