Lauren Brocato

Last updated October 1, 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 ART on THE MART, Halloween parades, live shows and much more. Plus, don't miss out on all the things to do at the Obama Presidential Center without a ticket 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

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 the Christkindlmarket. As the month draws to a close, bid adieu to 2026 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 2027 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

September might be here, but don't despair—there are still plenty of things to do in Chicago—whether you're still embracing a summertime state of mind or welcoming fall with open arms. From Oktoberfest celebrations to outdoor festivals (including Riot Fest), we've still got plenty of warm weather fun to take advantage of before the leaves start to turn and the temperature drops. Soak up the sun at the best Chicago beaches and rooftop bars, or spend your weekends checking out the end of festival season at events like the Chicago Jazz Fest and the World Music Festival. And if you really can't wait for fall to arrive, might we suggest some early leaf peeping and apple picking? Whatever your mood, you'll find plenty of ways to keep busy with our roundup of the best things to do in Chicago this September.  RECOMMENDED: Events calendar for Chicago in 2027

Once November hits, you've got about two weeks of breathing room after Halloween before holiday events begin in earnest, from twinkling Christmas light 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 with the help of our guide to the best things to do in Chicago this November. RECOMMENDED: Check out our 2026 Chicago events calendar

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

While the real world seems scary enough this year, Halloween still offers a lot of frightening thrills all its own. Plenty of Chicago bars, restaurants, hotels and special pop-ups are getting into the spooky spirit with days of Halloween festivities, from costume contests and creepy cocktails to full-on terrifying transformations. Whether you're looking for sinfully awesome celebrations from Michelin-starred chefs or a blowout bash with DJs and live performers, we have your Halloween plans covered. RECOMMENDED: The best Halloween events and parties in Chicago September 2026: There's no shortage of Halloween pop-ups and events happening throughout the month of October. Enjoy bites from acclaimed chefs at parties hosted by After and The Alston, sip cocktails from some of Mexico’s best bars courtesy of Three Dots and a Dash or dance the night away with dozens of DJs at Recess. However you choose to celebrate, there’s lots of spooky fun to be had.

Last updated September 30, 2026: Fall in Chicago is officially underway, which means it's time to turn your attention to all things spooky and ghoulish for Halloween. Hoping for a fright? Visit one of Chicago's most haunted places, attend one of the city's many Halloween parades and parties or wander through a ghostly haunted house. No matter your age, embrace the thrills and chills of spooky season with our guide to the best Halloween events in Chicago this year.  RECOMMENDED: Our complete guide to Halloween in Chicago Read more: The full list of scary movies coming to AMC FearFest 2026 is out now Hulu’s new Halloween documentary revisits 2016’s Great Clown Scare Watch the trailer for Prime Video’s new TV series ‘Carrie’

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. Updated September 30, 2026: Do you feel that? It's the Halloween spirit creeping into the city, and we're so excited to get spooky. This weekend, Halloween pop-ups, haunted houses, pumpkin patches and themed events are in full swing. Head to Jack's Pumpkin Pop-Up near Goose Island for a quintessential fall evening, or book a boat ride on the First Lady’s Creepy Cruise to learn about Chicago's haunted history. Keep scrolling to discover more of the best things to do in Chicago this weekend. RECOMMENDED: The best things to do in Chicago today

Summer in Chicago is fun, but the city really stands out in the fall when the trees start to change colors, a slight chill permeates the air, and there's an abundance of autumnal activities to enjoy. One of the best ways to celebrate the season? Visiting a corn maze. It’s nearly impossible to find one in the city, but just outside of Chicago, there are an array of farms and orchards that have elaborate—and sometimes seriously daunting—corn mazes to get lost in. With beautiful fall foliage, hay rides, apple picking and spooky mazes after dark, a visit to a corn maze is a great way to get into the Halloween spirit as well. So make the most of the season with a fun-filled day at the best corn mazes near Chicago. RECOMMENDED: Find the best pumpkin patches near Chicago

Each week, our team at Time Out Chicago curates the ultimate weekly event guide, featuring the big events, IYKYK pop-ups and everything in between. Here, you'll find the happenings that are worth your time and money, from family-friendly activities and daytime events to late-night shenanigans and the low-key functions that you won't hear about on TikTok. Updated September 28, 2026: Fall in Chicago is in full swing, and with it comes plenty of autumn activities to celebrate. Jack's Pumpkin Pop-Up is open near Goose Island; Halloween cocktail pop-up Black Lagoon is back at the Albion Manor; and the annual Lincoln Square Ravenswood Apple Fest is back with more than 100 vendors. There are plenty of ways to savor the sweet splendor of fall in Chicago, and we've curated a list of the best ones here. Keep scrolling for more of the best things to do in Chicago this week. RECOMMENDED: Discover the best things to do in Chicago in September 2026

There's no two ways about it: Chicago has one of the best comedy scenes in the country. Some of the most successful—and hilarious—comedians got their start here at clubs like the Second City and iO Theater. Household names like Tina Fey, Bernie Mac, John Mulaney and Chris Farley helped put Chicago's comedy scene on the map as a launch pad primed to send its top talents off to the big leagues. The next generation of Chicago comics is keeping the legacy alive. Our team of editors and contributors has scoured the stages (and dingy basements, restaurants and back rooms) for the 12 up-and-coming comedians that you should know about right now, and four of them hail from our very own Windy City.  This group is known for their smart writing, magnetic stage presence and undeniable hilarity that's on par with the city's greats. Our advice? Catch them at a show around town before they blow up—you'll thank us later. Special thanks to Teme Ring, who helped curate and craft our lists of Chicago comedians.

What’s the deal with West Town? If you’ve heard about a cool new spot in Chicago recently, there’s a good chance that it’s in West Town. Shaped by German, Polish, Ukrainian and Russian immigrants, and later by Puerto Ricans, Mexicans and African Americans, the flourishing community is home to some of Chicago’s liveliest culinary, art and cultural scenes. This West Side neighborhood comprises several distinct communities, including Ukrainian Village, Noble Square and East Village. Although the official boundaries vary depending on who you ask, it generally spans from the Chicago River to Kedzie Street, and between Division and Hubbard Streets. One thing is certain, though: Chicago Avenue is the beating heart of this vibrant community. If you only do one thing… Take a walk down Division Street. Start at Ashland Avenue and head west for a picturesque stroll through one of West Town’s busiest streets, stopping in any shops, galleries or restaurants that pique your interest along the way.  Photograph: Martha WilliamsBeadniks On a rainy day…  Create your own jewelry at Beadniks. This DIY charm bar also offers workshops, supplies and permanent jewelry installation. Afterward, bop over to Lost Larson down the street for delectable Scandinavian-style baked goods like cardamom buns and lingonberry cakes.  On a sunny day… Start your morning with one of Chicago’s best breakfast sandwiches from Michelin-starred Filipino restaurant Kasama. Place a pick-up order online before heading to

Chicago Seadog offers a spooky ride down the river and lake this season with its Haunted Tours. The 75-minute tours, offered on Fridays, Saturdays and Sundays through October, are moderated by a costumed guide, who shares the eerie history of supernatural occurrences in Chicago. Guests (and their dogs!) are encouraged to come in costume and BYOB if they want to get boo-zy on board.

This serene mecca of relaxation in an unassuming factory-turned-bathhouse offers a modern take on ancient Greek and Roman traditions. Dip in and out of hot and cold thermal baths, a flotarium (a saltwater bath that creates a feeling of weightlessness), a dry sauna and a steam room. Guests can elevate the experience by adding massages, and body and facial treatments to their wellness agenda. This is the perfect place to celebrate a special occasion with a small group, bring a date or visit by yourself just because. When you're in the baths, staff alerts you with peaceful bell sounds at various times so you don't have to watch the clock while you soak. You'll also have to wear water slippers the entire time you're in the baths area, but be careful because the floors can get slippery. After, head to the locker room to take advantage of the amenities like Dyson hair tools, bathing suit dryers, hair and facial products, and showers (though they aren't always in pristine condition, so we'd recommend waiting until you get home to wash up).

The team at Fulton Market restaurant Ever is hosting a 1980s-themed Halloween soiree across three spaces: After, The B-Side and The Canvas by Ever. A ticket to this spirited evening includes food and drinks, plus access to all three spaces throughout the evening. Each venue will transform into a different retro-inspired haunt, featuring horror film references, music and Michelin-level fare.

The Music Box Theater brings back its beloved annual Halloween tradition with five screenings of The Rocky Horror Picture Show. Each screening is paired with a shadowcast as actors perform in front of the screen during the film. It's a wonderfully weird tradition that's known to sell out.

International DJ Diplo pairs miles with music, and his touring run club is making its first stop in Chicago. The 5K run through Humboldt Park culminates with a live performance by the DJ himself. Runners can upgrade to the VIP Experience, which gets you access to a dedicated viewing area, exclusive sponsor activations, VIP entry and easy check-in on race day.

Six bars from Mexico City are popping up in River North this Halloween for Three Dots and a Dash's Terror in the Tropics: Midnight in Mexico celebration. The bars will each be pouring signature cocktails all night at Salon 61, where guests (who are encouraged to come in their best costumes) can enjoy DJ sets and the five drinks included with a GA ticket.

The Second City is reviving its annual Halloween series for a third time with Travel Can Be Murder, a 90-minute, unscripted whodunit inspired by Murder on the Orient Express and Death on the Nile. Based on a single audience suggestion, performers build a live, on-stage mystery that the audience must solve before the final line. 

Queen cover group Queen Symphony Sensation is performing in the U.S. for the first time, and the 28-person group is stopping in Chicago for a night packed with the band's greatest hits. A live rock band, symphony orchestra, choir, soprano and two lead vocalists will perform powerful renditions of songs like "Bohemian Rhapsody," "We Will Rock You," "Somebody to Love" and many more.

Apple cider, fresh doughnuts and more than 30 varieties of apples abound at Jonamac Orchard located about an hour and a half outside of the city. After filling up your bag with the season's freshest apples, pick out pumpkins and fresh flowers before enjoying food and drinks from the on-site bars and food trucks. With a variety of activities like hayrides, apple cannons and a haunted corn maze, there's something for the whole family to enjoy.

Celebrate wellness, art and health at the free one-day festival, Healing Arts Chicago Summit. Chicagoans are invited to participate in programming like artist-led workshops, sit in on panels focused on workforce development, and join yoga, dance, movement and journaling sessions. 

You don't need alcohol to get in on the Oktoberfest fun. Head to Mocktoberfest at Palmhouse in suburban Evanston for a zero-proof celebration, with non-alcoholic drinks, German-themed food, live music and an artisan marketplace. Tickets include unlimited beverage samples, plus free chair massages and tarot readings, table games, a stein-holding contest and more.

Explore limited-edition comics, artist books, zines and art by more than 100 artists and independent publishers at Pretty Good Fest. The free fair features exhibitors, readings and other events, plus programming with special guests and acclaimed cartoonists Chris Ware, Michael DeForge and Tara Booth.

If an Hermès jacket and a Shein jacket weigh the same, then they cost the same. At least that’s the way it works at Happy Belated Clothing. At the Wicker Park thrift shop tucked underneath the Blue Line tracks at 2025 W North Avenue, nothing is tagged or tracked, which means customers pay by the pound at $10 per pound. Since opening in late 2024, Daley has sourced thousands of pounds of stock from a recycling plant in Japan to fill the sizeable—albeit dimly lit—store. Happy Belated is one of the few places in Chicago where you can buy clothing by the pound, and because everything comes from Japan, there’s more variety than a typical thrift store. Vibrant colors, charming plushies and trinkets along the walls, and a disco ball set the scene for the kind of experience you’ll have here sifting through the extensive selection of mens and womens garnments. Photograph: Lauren Brocato for Time OutHappy Belated Clothing   RECOMMENDED: The best thrift stores in Chicago These are discount recycled pieces, so don’t expect to score designer every time. You’ll usually come across foreign and bygone brands, but every once in a while, you’ll find a needle in the haystack. One of the best recent scores was a Christian Dior blouse, likely valued at over $500, that sold for $2.98. Customers have also found high-value items from brands like Coach and Kate Spade, and as an employee told me, the lowest amount someone has paid for their items recently was 89 cents.  View this p

The Center of Order and Experimentation is definitely not a cult. And their website and signage out front will consistently remind you that they’re not. The West Town shop, located at 1727 West Grand Avenue, is a fantastically peculiar boutique that stocks “unexpected goods for unexpected times,” as their website states.  Jean Cate and Julie Purpura opened COE, which looks like it’s been plucked from the mind of Wes Anderson, four years ago. Since then, it’s become a beloved destination for curious knickknacks and a go-to for excellent coffee (courtesy of the on-site Monday Coffee Co. outpost), and is a focal point of the community’s vibrant creative scene. Photograph: Lauren Brocato for Time OutOutside The Center of Order and Experimentation Cheeky anti-cult branding gets people in the door, literally: a sign out front reads “NOT A CULT!” But warm greetings from staff and COE’s Head of Customer Satisfaction, a 15-year-old Cavalier King Charles spaniel named Martha who sits floppily in a basket at the checkout counter, pull you into the shop’s whimsical world that “transcends geographical boundaries and exists in a realm where order and experimentation harmoniously coexist,” as their website notes. RECOMMENDED: West Town, Chicago: The ultimate neighborhood guide Stock rotates regularly, but the curation is based around helpful utility. On any given day, you might find designer pocketknives, scissors and flashlights presented alongside high-end Japanese stationery and an orn

Get ready to rock out because Riot Fest is back for three days this weekend. More than 100 punk, alternative and metal acts are in Douglass Park for the 21st edition of this annual music festival. This year's lineup is stacked with heavy hitters like Twenty One Pilots, Iggy Pop, Nas, Tool, Pierce the Veil, Alanis Morissette and many more. There's also a roster of late-night aftershows across the city at venues like Metro, Empty Bottle and Concord Music Hall. For the first time, festivalgoers can park at the official Riot Fest parking lot. Parking passes start at $50 per day, and the lot is about a 10-minute walk from the fest, so public transit may still be your best option. The CTA Pink Line's California stop is just a few blocks away. No matter how you get there, you'll want to have an on-the-ground plan. Grab your crew and your favorite band tee and plan your festival weekend with the complete Riot Fest lineup and schedule below. What are the Riot Fest set times and schedule? All three daily schedules are listed below, both in image and text format. There are more than 110 acts, but the biggest ones to watch for are Twenty One Pilots at 8:40pm and Iggy Pop at 8:45pm on Friday; Tool at 8:40pm and Nas at 9pm on Saturday; and Pierce the Veil at 8:25pm and Insane Clown Posse at 8:55pm on Sunday.  Photograph: Courtesy Riot FestFriday schedule Friday, September 18 Riot Stage Cardinals: 12–12:30pmJMSN: 1:10–1:40pmViolet Grohl: 2:20–2:50pmThe Paradox: 3:30–4pmJoey Valence & Bra

There’s no denying that West Town is having a moment—that’s why our team at Time Out has named it the coolest neighborhood in Chicago and the No. 18 coolest neighborhood in the world. Time Out editors from across the globe ranked the top 40 coolest neighborhoods in the world, from an artsy enclave in Tokyo and a waterfront sanctuary in Brisbane, to Stockholm’s meatpacking district and an under-the-radar town in Montreal.  West Town is home to some of the city’s best restaurant and bar debuts in recent years (Pizz’amici, Bar Bambi and Guillotine Bakery, to name a few) and new cultural destinations like Elise Seigenthaler Gallery and Bridgeport Records’ newest shop, Onion City Records. West Town has, of course, been cool for many years, thanks to its many iconic restaurants, museums, bookstores, green spaces and shops. RECOMMENDED: The ultimate West Town, Chicago neighborhood guide Shaped by German, Polish, Ukrainian and Russian immigrants, and later by Puerto Ricans, Mexicans and African Americans, the flourishing community is home to some of Chicago’s most exciting culinary, art and cultural scenes. The West Side neighborhood comprises several distinct communities, including Ukrainian Village, Noble Square and East Village. Although the official boundaries vary depending on who you ask, it generally spans from the Chicago River to Kedzie Street, and between Division and Hubbard Streets. One thing is certain, though: Chicago Avenue is the beating heart of this vibrant communi

When romance bookstore Last Chapter opened in Roscoe Village in mid-2023, a line of excited readers stretched down the quaint block on Roscoe Street. This turnout wasn’t a surprise, though: Chicago’s been home to popular specialty bookstores for decades, and more have continued to pop up in recent years. From horror-themed shops to manga meccas, there are a handful of top-notch niche bookstores that have become vibrant community hubs for their respective fanbases. Some carry rare titles and limited-edition collectibles, while others also sling themed merch, memorabilia and other physical media.  Want to discuss the ending of your last great read or swap recommendations with other readers? Check out these bookstores’ events, which range from author talks and book clubs to art workshops and album release listening parties. Whether you’re looking for a like-minded literary community or are curious about where to start with a new genre, here are our favorite specialty bookstores in Chicago. RECOMMENDED: The best bookstores in Chicago for new and used books Goblin Market View this post on Instagram A post shared by Goblin Market Manga, Comics & Curiosities (@goblin.mkt) When it opened in 2023, Goblin Market was one of Chicago’s first manga shops. The Lakeview storefront is packed with manga and graphic novels of all varieties, plus comics, games, puzzles and merch. Check out Goblin Market’s calendar for events like queer nerd meetups, silent book clubs, b

Whether you’re ready or not, summer is coming to a close. It’s been a busy one, filled with monumental moments like the Obama Presidential Center opening, America’s 250th anniversary, WNBA All-Star Weekend, and so much more. But Labor Day weekend is here, and it’s finally time to say goodbye to summertime Chi. With a sunny (for now) forecast predicted over the next few days, it’s only right to get out and make the most of the coveted three-day weekend and celebrate what the national holiday is all about: celebrating the contributions of the American worker. Ready to send summer off with a bang? Here are our picks of the best events and things to do over the long weekend. For our full guide to more than 40 things to do this weekend, click here. RECOMMENDED: The 16 best bars for day drinking in Chicago 1. Chicago Labor Day Parade & Eddie Fest The Chicago Labor Day Parade returns to historic Pullman on Saturday. Organized by the Chicago Federation of Labor, the event celebrates union pride, solidarity and community togetherness. The parade will step off at East 112th Street and South Avenue F on the Southeast Side, before continuing north up South Ewing Avenue to East 106th Street. Afterwards, stick around for Eddie Fest, featuring live music, food and family-friendly activities, at Steelworkers Park.  2. Chicago Jazz Festival As is Labor Day weekend tradition in Chicago, some of the biggest names in jazz will gather for a series of shows through Sunday at Pritzker Pavilion in M

Did you know you can stream blockbuster movies, TV shows and music for free with a Chicago Public Library card? What about the fact that you can get a free language learning app subscription? A CPL card is more powerful than you think.  The perks of being a CPL cardholder go far beyond being able to check out books. In addition to thousands of events across the 82 branches, many of which are also open to non-cardholders, there are many free things you can do just by having a library card. Any Chicago resident can register for a free library card. All you have to do is bring a valid ID with your name, photo and address to any CPL branch and fill out a simple application. Children under 14 are eligible for a youth card, and students have access to additional card options.   RECOMMENDED: 11 things you can do at the Obama Presidential Center without a ticket Whether you’re headed to the new branch at the Obama Presidential Center or one of the many other beautiful libraries, there are dozens of free services and experiences that cardholders have access to—you just need to know where to look. Here are the best free things you probably didn’t know you can do with a library card. 1. Get into Chicago museums With a CPL card, you can get into most Chicago museums for free by reserving a pass online. Just show up at the museum at your reserved time with your digital pass and ID, and enjoy a day of discovery.  2. Stream movies, TV shows and music Free access to entertainment streaming s

The Great Lakes are the "last uncruised region of the world," according to Stephen Burnett, the former executive director of the Great Lakes Cruising Coalition, in 2019, but several companies have been working to change that. This year, voyages throughout the region increased nearly 5% since last year, marking continued growth in popularity since the pandemic completely halted all cruise tourism between Canada and America.  You might think that Chicago, the largest U.S. city in the Great Lakes region, would be the busiest and most important hub on these routes. But that’s not the case, as nearby cities like Milwaukee, Cleveland and Toronto see significantly more cruise traffic.  Just two of the seven cruise lines voyaging through the Great Lakes this year stopped in Chicago: Viking Cruises and Victory Cruise Lines, and only the latter actually docked at Navy Pier.  RECOMMENDED: Don’t want to pay for a pricey Chicago River cruise? Book this $10 ride instead. Many Great Lakes cruises include Chicago on their itineraries, though passengers are often shuttled to and from other port cities for the day. So why do most cruise lines skip over docking in Chicago on their journeys? The answer is pretty simple: Navy Pier isn’t big enough.  Most vessels exceed Navy Pier Marina’s capacity to accommodate ships shorter than 183 feet long. Viking’s much larger ships, like the one many confused Chicagoans spotted out on the lake earlier this summer, got around the size restrictions by anchori

If you’re walking down the lakeshore this weekend and see hundreds of shiny heads gathering, don’t be alarmed; it’s just the Chicago Bald-Off. The viral Chicago Bald-Off is back for a second year, and it’s going to be bigger and balder than ever before. The *very* serious competition (I’ll let you decipher what that means) will take place at 5pm on Sunday, August 30 in Lincoln Park. Just like last year, Chicagoans will crown the city’s “Baldest Baddie” and “Baddest Baldie.”  In true brainrot fashion, the official announcement (some paper signs taped up around Chicago) gives only the location’s coordinates, 41.93908, -87.63416. For those who don’t know off the top of their (bald) head where that is, it’s the Self-Portrait sculpture at the AIDS Garden.  RECOMMENDED: A controversial statue could make a return as part of a new museum opening this fall Chicago Bald-Off organizers have asked competitors to “come correct” (AKA bald or donning a bald cap), though people of all hair levels are welcome to attend. The poster also reads, “This is NOT a drill. This is a COMPETITION.” All Pitbull, Cynthia Erivo and Poot Lovato doppelgangers are encouraged to compete.  @chicago.bald.off 2026 CHICAGO BALD OFF IN LAKEVIEW ON 8/30. you know the drill but this is NOT a drill !!! #chicago #lakeview #contest #whimsy #bald original sound - The Washed Athlete After last year’s Bald-Off, which garnered national attention, and the headline-making Jeremy Allen White look-alike contest of

Yes, you read that right. NASCAR just announced that the downtown Chicago street race will not return in 2027. The decision came after the city and NASCAR ran out of time to agree on a 2027 date.   Instead, the Cup Series race weekend will be held at Chicagoland Speedway in suburban Joliet, about an hour outside of the city, from June 25 to June 27, 2027. This marks the second year in a row that the race takes place in Joliet, after NASCAR traded the streets for the Speedway earlier this year. NASCAR first took over the streets of Chicago in 2023 over Fourth of July weekend, notoriously bumping Taste of Chicago out of its signature Independence Day time slot. The debut race weekend was defined by abysmal weather, a truncated race, multiple delays and the cancellation of all three scheduled concerts by The Chainsmokers, Miranda Lambert and Charley Crockett.  RECOMMENDED: Chicago's most iconic street party was cancelled—here's why The following two years brought wet weather and extreme heat, but were far less chaotic than 2023. Despite more favorable conditions and cheaper tickets, Chicagoans weren’t totally sold on the street race. Many residents still complained about things like extensive street closures and parking restrictions, and still-high ticket prices (a single-day ticket went for $99 in 2025). Even the drivers weren’t all in, as they expressed concerns about the possibility for crashes on the track. View this post on Instagram A post shared by NASCAR

Get ready to bust a move because Chicago SummerDance is back with free dance classes in Grant Park for just nine nights this month. The lineup for the series’ final installment, Chicago SummerDance in the Spirit of Music Garden, is packed with beginner-friendly classes across dance styles, all informed by the city’s rich cultural landscape. From ballroom and Bollywood to Brazilian samba and Chicago steppin’, there’s something for everyone—even those who claim to have two left feet. SummerDance classes are completely free and open to dancers of all ages and experience levels. Instructor-led dance lessons kick off at 6pm and are followed by live music performances—with plenty of room to show off your new moves—at 7:15pm.  RECOMMENDED: Chicago's most iconic street party was cancelled—here's why A special edition of SummerDance, hosted by Chicago musician and media personality Dana Divine, will be held during the annual Chicago House Music Festival weekend. BraveSoul Movement will lead a house dance workshop at 6pm before DJs Ron Troupe (6:30pm) and Mark “Flava” Fuller (7:45) take the stage.  “Chicago SummerDance is one of many ways that the Department of Cultural Affairs and Special Events activates and transforms public spaces into vibrant areas for people to connect through culture,” says DCASE commissioner Kenya K. Merritt. “These live performances and free dance lessons celebrate the traditions and communities that define Chicago while making arts and culture accessible in n

Those deafening roars from above are nothing to be afraid of—it’s just the annual Chicago Air and Water Show.  This weekend, the roaring spectacle returns to the skies of Chicago for two days (well, three if you count Friday’s rehearsal) of high-flying stunts, daring tricks and spectacular maneuvers for a crowd of nearly 2 million people. The festivities kick off with a practice on Friday, August 14, followed by the official show on Saturday, August 15 and Sunday, August 16, from 10:30am to 3pm. As always, the show is free to watch—all you have to do is look up.  North Avenue Beach is the central hub, but you’ll still be able to see the show from plenty of other spots along the lakeshore.  View this post on Instagram A post shared by Air Force Thunderbirds (@afthunderbirds) This year’s air show will look a little different as the U.S. Air Force Thunderbirds return for a second year in a row, rather than the typically alternating U.S. Navy Blue Angels due to a scheduling conflict. We’re still in for a remarkable show featuring a lineup of military and civilian performers, including the U.S. Army Parachute Team Golden Knights. Legendary moderator and retired Air Force pilot Herb Hunter will once again voice the show, which you can hear from Oak Street Beach to Fullerton Beach.  Read on for all of the essential information about this year’s Chicago Air and Water Show. Who are the military performers in the Chicago Air and Water Show 2026? U.S. Air Fo