Shannon Shreibak

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 music 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 Hyde Park Jazz Festival, Printers Row Lit Fest and Taste of Chicago. 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: Check out our 2025 Chicago events calendar

The annual Oktoberfest celebrations mark the arrival of fall, but even if you can't make it to Munich, plenty of Chicago institutions are throwing bustling, German-themed parties to ring in a new season. From special tappings at Chicago breweries to carnival rides outside neighborhood churches, we've gathered some of the best parties and events during Oktoberfest in Chicago, taking place at amazing restaurants, food halls and even zoos. Break out those dirndls and lederhosen and prepare to say "Prost"! What is Oktoberfest?  Oktoberfest is a multi-week beer festival and fair held in Munich, Germany. Originally conceived to celebrate the marriage of Bavarian King Ludwig I and Princess Therese of Saxony-Hildburghausen in 1810, the festival has since evolved into a public event and one of the most important cultural symbols in Bavaria, drawing millions of attendees from across the world each year.  When is Oktoberfest in Chicago? Although Munich's Oktoberfest takes place this year from September 20–October 5, Chicago's celebrations generally take place anywhere from mid-September to mid-October.

There’s no surer sign that fall is coming than seeing pumpkins everywhere—whether used in fancy coffee drinks, recipes or just as decorations, pumpkins are the ubiquitous symbol of autumn. Maybe you don’t love pumpkin spice lattes or pumpkin pies, but it’s hard to deny the appeal of choosing your own perfect-to-you gourd at a pumpkin patch. All of the farms and pumpkin patches on this list are within a two hour drive from the city (one is even in Chicago), and bursting with fall fun. After you’ve picked out a jack-o’-lantern, spend the day exploring creative corn mazes, eating apple cider donuts and checking out fall foliage. RECOMMENDED: Your complete guide to fall in Chicago

Fall in Chicago has arrived, and with it comes a colorful burst of fall foliage throughout the city. According to this interactive guide, which uses an algorithm to predict when the leaves will change, local trees will start showing patchy colors the week of September 30 and hit their peak in late October. Hoping to go leaf peeping this year? Head to some of the more well-known Chicago parks and gardens to see towering oaks and fiery red Japanese maples, or take a contemplative stroll through a cemetery to watch yellow weeping willows drape over a leaf-filled pond. Plus, if you're itching to take a quick day trip from Chicago, you'll find several suburban conservatories and arboretums worthy of an afternoon leaf-peeping expedition. So take a look through our roundup of the best places to see fall foliage in Chicago and get ready for some scenic sights. RECOMMENDED: Find the best places to see fall foliage outside of Chicago

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 take part in. One of the most fun ways to celebrate the season? Visiting a corn maze. It’s nearly impossible to find one in the city, as you need a pretty large field, but we've traveled just outside of Chicago to nearby suburbs to find find a wide array of farms and orchards that have creative and sometimes daunting corn mazes to get lost in (plus apple picking). Open through the end of October, some of them serve as a festive 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

Sometimes a sunny day can only be made more perfect by sipping on a cold drink outside. The best Chicago breweries and taprooms offer plenty of space to try their latest beers fresh from the tap, while outdoor bars and beer gardens offer relaxed places to gather with friends and share some brews. Many beer gardens and outdoor spaces are dog-friendly, too, so don't hesitate to let your pup in on the fun of a beautiful day. Whether you're itching for better weather or want to create your own impromptu beer garden crawl, here are the best beer gardens in Chicago for a cold beverage on a warm Chicago day. RECOMMENDED: Discover even more of the best bars in Chicago

Looking for an outdoorsy experience that's a bit more adventurous than walking through your local Chicago park? Thankfully, you don't need to go too far to escape the urban jungle, because there's no shortage of great spots for hiking near Chicago. Cross state lines to visit the gorgeous Indiana Dunes along Lake Michigan, explore the ruins of a steel mill in Joliet or tackle the sprawling 30-mile Ice Age Trail at Kettle Moraine State Forest in Wisconsin. Plus, some of these paths double as great Chicago bike trails—you can even make a weekend of it and plan a camping adventure. If you're ready for a quick escape from the city, put on your best boots and hit the trails at some of the best places for hiking near Chicago. RECOMMENDED: Hit the road on more day trips from ChicagoDiscover these amazing treehouse Airbnbs near Chicago

As a chill runs through the air and the leaves begin to change, it’s not just fall that’s upon us, but spooky season. Autumn is the perfect time to watch horror movies, tell scary stories and walk through haunted houses. If you’ve ever wanted to have a real paranormal encounter, though, Chicago has plenty of destinations to try and make that happen. Historic buildings aren't the only places that have reported hauntings—music venues, cemeteries and hotels all have ghost stories surrounding them as well. So for those who are looking for more than pumpkin patches and corn mazes this fall, we’ve put together a list of some of the most haunted spots in Chicago that offer a truly chilling experience. RECOMMENDED: Our complete guide to Halloween in Chicago

If you're angling to spend an afternoon soaking in quiet natural settings, classic architecture and plenty of historical lore, look no further than Chicago's cemeteries. These contemplative locales, some of which date back to the 19th century, serve as the final resting spots of countless famous Chicagoans—so many, in fact, that you could spend hours getting lost among the stately tombstones and crypts studding their manicured grounds, which rival even the most scenic Chicago parks. Unsurprisingly, many of these spots also number among the most haunted places in Chicago, so try not get too scared when you visit the most beautiful cemeteries in Chicago. RECOMMENDED: The best haunted houses near Chicago

Not sure how to spend your week? We’ve got you covered! The city’s music scene is buzzing, with North Coast, ARC and Ravinia Festival hosting world-class acts throughout Chicagoland. If sunshine is calling your name, soak it up at Sunset Skyline Yoga or Bike The Drive, when Lake Shore Drive transforms into a colossal bike lane for one blissful morning. Food lovers, rejoice—Wing Out and Taste of Polonia are back, serving up can’t-miss bites all weekend long. If you’re still looking for Labor Day weekend plans, look no further than our Labor Day 2025 guide, highlighting the city’s best events, beaches, rooftop bars and more. RECOMMENDED: Discover the best things to do in Chicago in August 2025

Over the past couple of years, Chicagoans have reconnected with the romantic summer tradition of the drive-in. While you can definitely grab some popcorn and still catch an outdoor movie in a park, a summer blockbuster at the best movie theaters in Chicago or even a cult classic on a Fulton Market rooftop, there's still something to be said for the feeling of pulling up to the big screen, setting up a tailgate-style spread with friends or getting cozy for a unique date at the drive-in. Whether you want to make the trip to McHenry or see a movie in a Pilsen parking lot, the best drive-in theaters near Chicago are worth checking out. Just make sure those windshields are clean. RECOMMENDED: The best dine-in movie theaters in Chicago

Even some of the best ice cream shops in Chicago can't compare to the rush of unwrapping a classic chocolate bar or tearing open a bag of sour gummies. On top of such a sweet sentiment, these desserts are fit for all seasons: silky caramels for autumnal indulgence, cloud-like marshmallows for out-of-this-world s'mores over a midsummer campfire or a bouquet of confections to complement the perfect floral arrangment from a local flower shop. No matter the time of the year, satisfy that sweet tooth at the best candy and chocolate shops in Chicago. RECOMMENDED: The best hot chocolates in Chicago

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.

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.

There's a new kid on Chicago's street festival scene, and this one promises to be unlike anything else. Edgewater will be hosting over 35 musical acts—including indie rock mainstays Cloud Nothings, Chicago hip-hop standout Ric Wilson and local drag punk outfit Bev Rage & The Drinks—and 100 vendors for the inaugural Edgewater Music Fest. The fest is open to all ages, with a Kids' Zone activity area for the little ones.

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.

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.

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, Mary Lattimore and Mary Lattimore, with surprise sets curated by Electrical Audio—the recording studio founded by the late Steve Albini—still to be announced, but sure to be a treat for the ears. Read more about Sound & Gravity's inception here.

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.)

If Wes Anderson designed a cafe-meets-gift shop, it would probably look a lot like The Center for 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.  

Paying homage to Japan’s convenience stores (konbinis), Konbini & Kanpai melds grab-and-go convenience with the warmth of a friend’s living room. The shop offers bevies for any and every occasion, from premium sakes and Japanese wines to local craft beers and tallboys of Guinness. For non-imbibers, Konbini & Kanpai also offers a wide selection of non-alcoholic drinks and Asian snacks.

Get ready to move, Chicago: Salt Shed is debuting a first-of-its-kind wellness festival on Sunday, September 21. Combining mindfulness, fitness and music, Move At The Shed is a choose-your-own-adventure festival, inviting attendees to build an experience that makes them move and connect. Salt Shed has been hosting run clubs and community yoga classes throughout its tenure, and the venue is doubling down on its commitment to fostering community through movement. Stacked with offerings from local fitness studios—like The Sunroom and Common Language—as well as vendor experiences, sponsor activations, and more, Move At The Shed is an adventurous new endeavor for the venue. From 11am to 7pm, Salt Shed’s iconic industrial digs will transform into a sanctuary for Chicago’s movers and shakers. Curated by 16” on Center (the team behind Chicago institutions like Empty Bottle and Thalia Hall), Move At The Shed invites attendees to recharge through yoga, dance, somatic breathwork and more. A Salt Shed event wouldn’t be complete without music, of course— a yoga flow and sound bath featuring a live performance from Jamila Woods and a meditation and movement workshop with Vic Mensa will round out the day. Attendees can purchase individual tickets to sessions or opt for a $15 Community Pass, which unlocks access to vendors, lounge areas, activations and open movement offerings like group runs and strength demos. Ticketholders can also take advantage of discounted add-on sessions throughout t

We made it, y’all—Labor Day weekend, summer’s bittersweet swan song, has arrived. And it comes with no shortage of ways to soak up the season’s final long, sunny days. Feeling overwhelmed by the endless possibilities? Fear not—we’ve scoured the city’s packed calendar to bring you the very best festivals, events and activities to make the most of your three-day weekend. 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 at Pritzker Pavilion in Millennium Park and the Chicago Cultural Center during this annual festival. This year's headliners include composer Esperanza Spalding, saxohponist Ari Brown and drummer Greg Fundis. Visit the Chicago Jazz Festival webpage for the full lineup and schedule. Be awed by the final Navy Pier Fireworks show of the year During the summer, one of the best aerial displays you’ll find in Chicago originates from Navy Pier. The Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays and Saturdays) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier’s public spaces. Of course, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.   Photograph: Courtesy Music Box Theatre   Catch a movie at the last-ever Music Box Garden series During the summer, spending more time indoors than absolutely necessary feels almost sacrilegious. The Music Box Theatre gets it—and ful

Chicago’s iconic ART on THE MART projections will light up the Riverwalk once again this fall, debuting a new visual experience on September 11. City Circle Heart—a collaboration with local nonprofit Arts of Life, which is celebrating 25 years of supporting artists with intellectual and developmental disabilities—will adapt the work of Arts of Life artists for the Merchandise Mart’s larger-than-life canvas. Originally created for the 2020 ART on THE MART projections, City Circle Heart weaves together colorful, abstract visuals into a dynamic moving display, complete with its own unique soundscape. Featuring work by Marcelo Añón, Veronica Cuculich, Stefan Harhaj, Hector Jones and Maria Vanik, City Circle Heart invites people of all abilities to appreciate the movement, colors and beauty of the Chicago Riverwalk.  “Arts of Life is thrilled to showcase our artists and celebrate our 25th anniversary with a featured presentation on ART on THE MART,” Arts of Life cofounder and executive director Denny Fisher said in a press release. “This is an ideal opportunity to highlight our commitment to supporting artistic expression, to providing professional development opportunities for artists with intellectual and developmental disabilities, and to introducing our artists’ work to new audiences.” 

 Founded in 2018 in partnership with Chicago’s Department of Cultural Affairs and Special Events, ART on THE MART is one of the world’s largest digital art platforms (after all, it’s hosted on

As Oasis blaze through their long-awaited reunion tour, the Britpop legends have announced official merch pop-ups in select cities—including (praise be) Chicago. After successful runs in the U.K. and Ireland, the pop-up shops will land in select North American cities, with Los Angeles, Toronto, New York and Chicago among the chosen few. Fans can expect not only official tour merch and limited-edition items but also pieces from the hotly anticipated “adidas Originals x Oasis” collection. For the vinyl collectors out there, exclusive tour-edition colored LPs from the Oasis catalogue will also be available, each accompanied by a special Live ’25 print found only at the fan stores. Rounding out the exclusives are graphic tees featuring iconic Oasis album and single artwork, including Definitely Maybe, (What's The Story) Morning Glory?, “Wonderwall” and “Supersonic.”   Photograph: Courtesy of Hustle&Co. The Chicago outpost of the Oasis Live ’25 Fan Store will open its doors on Tuesday, August 26, at 10am—two days before they take the stage at Soldier Field. The shop will be located in the heart of Wicker Park at 1421 North Milwaukee Avenue. Walk-ins will be welcomed, but to avoid an assuredly long wait, hopeful shoppers are encouraged to book their visit in advance here.

Chicago’s skies are about to see a lot of action this weekend—the Air and Water Show returns! The annual spectacle will take place August 16 and 17, with a rehearsal day on August 15. Whether you’re a jet-loving local or a first-timer looking to soak up one of the city’s most iconic experiences, the Air and Water Show delivers patriotic flair, family-friendly thrills and more than a few moments that’ll leave you looking up in awe. Folks will be able to see dazzling aerial demonstrations from an array of acts, including the return of the U.S. Air Force Thunderbirds and the U.S. Army Parachute Team Golden Knights. The show will run from 10:30am to 3pm on both days and, as always, admission is free. North Avenue Beach is the central location for the festivities, but you’ll be able to view the action from various spots along the shore. The city installs white and green pole markers in Grant Park for easy reference points and emergency info, so take note of your nearest one. As always, the show will be moderated by Chicago legend and retired Air Force pilot Herb Hunter, known as the “voice” of the Chicago Air and Water Show—Herb has been the show’s announcer since 1988. RECOMMENDED: Where to watch the Chicago Air and Water Show Who are the military performers in the Chicago Air and Water Show 2025? – U.S. Air Force Thunderbirds– U.S. Army Parachute Team Golden Knights– U.S Air Force C-17 Demo– Illinois Air National Guard KC-135– Maryland Air National Guard A-10’s– U.S Coast Guard

To the surprise of no one, Chicago has been named one of the world’s best cities for Generation Z. In Time Out’s global ranking by Gen Z and for Gen Z, Chicago comes in at number 17. But if we narrow the list to “USA’s Best Cities for Gen Z,” Chicago lands and number two, beat out only by New York. You may be (rightfully) wondering, how do we know Chicago is so great for Zoomers? Based on the same data as our Best Cities survey—but filtered to responses from those under 30—this ranking highlights the cities where the next generation truly thrives, specifically on metrics like happiness, food scene and overall vibe. Locals are well aware that our incredible city has no shortage of amazing things to do—from pop-up markets and music festivals to world-class museums and attractions—no matter the season. And, of course, we can’t forget about Chicago’s widely celebrated food scene. While everyone knows about the city’s most iconic eats, like deep dish pizza, Chicago-style hot dogs and Italian beef sandos, the depth of Chicago’s culinary offerings cannot be understated. Want to try some of those delicious stand-out bites in person? We've got it all—and more—at Time Out Market Chicago, where you can experience everything from trending pop-ups to the city's most famed dishes. RECOMMENDED: Experience the best of the city at Time Out Market Chicago Topping the 2025 global ranking is Bangkok, trailed by Melbourne, Cape Town and Copenhagen. In the worldwide ranking, Chicago is joined by

Prost, Wrigleyville party people! Oktoberfest is coming to the North Side this year thanks to the Chicago Cubs. This September, the North Side will host the first-ever “Oktoberfest with the Cubs,” a festival celebrating beer, brats and more. The three-day, all-ages event will take place Friday, September 19, through Sunday, September 21, in the Toyota Camry Lot, situated just outside Wrigley Field on Grace Street. Keep in mind there will be no access to the inside of the Friendly Confines during the weekend’s festivities. “We’re thrilled to bring this new event concept to the Wrigley Field campus later this year in celebration of Oktoberfest,” Cubs senior director of event operations Morgan Bucciferro shared in a press release. “This event is not just for Cubs fans. It’s for the community, neighbors and those looking to have a good time on a weekend in September. Gather your friends and join us outside the ballpark for the first-ever Oktoberfest with the Cubs—this is not an event you want to miss!” RECOMMENDED: Chicago’s 2025 festival season dates: Everything you need to know “Oktoberfest with the Cubs” promises beer tents with a wealth of boozy brews, authentic food offerings, carnival attractions (ride tickets required), a stein-holding competition and much more. Pint-sized attendees can enjoy a Kinderfest, complete with kid-friendly crafts, balloon artists and family-friendly competitions. Tickets are required to attend, with single-day general admission tickets costing $1

Have you ever found yourself wandering around Millennium Park, gazing into the reflective splendor of “The Bean” and wondered, “Is there a man hopelessly trapped in there?” Probably not—unless you’re a card-carrying member of the “Man In Bean Coalition,” a viral (and possibly performance art) stunt that’s been making waves online and beyond. While thousands descended on Grant Park for Lollapalooza last week, a small group of “protesters” spent the weekend picketing at the foot of Cloud Gate (that’s “The Bean’s” government name). Dressed in all-black and waving signs scrawled with slogans like “UNLOCK CLOUDGATE” and “YOU WOULDN’T PUT A BABY INSIDE A BEAN,” they quickly caught the attention of Millennium Park security—and Chicago at large. The group also handed out flyers urging bystanders to contact Alderman Brendan Reilly’s office, whose ward includes Millennium Park. RECOMMENDED: The most hilarious events happening at the Bean, according to Facebook Alderman Reilly’s office was inundated with so many calls that he was compelled to share a public statement, calling the Man In Bean Coalition an “online hoax.”  “I am happy to confirm that a man has not been trapped inside Cloud Gate (a.k.a ‘the Bean’) for the past 21 years. In fact, the man was freed years ago,” the statement reads. “Further, we can neither confirm nor deny that Soldier Field is actually a flying saucer secretly relocated from Area 51 back in 2003.” The Man In Bean Coalition’s sole social media account, an Ins