Shannon Shreibak

August 2025: We’re in the midst of our last full month of “summertime Chi,” but the fun is far from over. August brings with it some of Chicago’s best seasonal events, from the annual Chicago Air and Water Show and Northalsted Market Days to summer festivals like Lollapalooza, North Coast Music Festival and Riot Fest. If that’s not your speed, you can also check out the dazzling floral displays at the Chicago Botanic Garden, hop on the First Lady’s Canine Cruise or, always a summertime favorite, take a Rainbow Cone to the dome. Options abound this month, so soak up summer fun before we’re all dusting off our puffer coats for winter. 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. You can also find out more about how Time Out selects the very best things to do all over the world, or take a look at our list of the best things to do in the world right n

We may be savoring our last full month of summer in Chicago, but the fun is far from over. August brings with it some of Chicago’s best seasonal events, from Taste of Chicago and Bike the Drive to summer festivals like Lollapalooza, North Coast Music Festival and Riot Fest. Don't forget to plan a couple of languid afternoons at the best Chicago beaches—Lake Michigan's often frigid water is at its warmest this month. Looking for even more ways to make the most of the remaining summer days? Scroll through our list of the best things to do in Chicago this August. RECOMMENDED: Events calendar for Chicago 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. Every week, we curate a Chicago weekend itinerary packed with the city’s best concerts, culture and cuisine. This weekend, trek up to the Chicago Botanic Garden to feast your eyes on their new exhibit “Patterned by Nature,” a celebration of the patterns and prints that adorn the natural world. For those yearning for drama, check out the Neo-Futurists’ signature show The Infinite Wrench. If you find yourself battling a Sunday slump, macrodose some coffee and cumbia at Drip Collective’s Hot Drip Sessions or catch The Paper Machete at The Green Mill. RECOMMENDED: Discover the 50 best things to do in Chicago right now

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.

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.

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.    

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.)

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.

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.

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.  

Since staking their claim on Ravenswood’s flourishing “Malt Row,” Is/Was Brewing has emerged as an authority on saison-style beers. Their success has echoed far beyond Chicago, too—recently being crowned one of the top saison producers in the world by Craft Beer & Brewing. To celebrate six years in business, Is/Was will be releasing their first-ever canned offering: a 16-ounce version of their flashship saison, Will Be, which was previously only available in kegs and 500-milliliter bottles. On the day of their anniversary celebration, Is/Was will be offering the cans for a cool $6 along with glizzies and chips from Cash's Kitchen plus live portraits by Joe Kraft, the artist behind the brewery's whimsical branding.

A spot on the pine bleachers at Drip Collective has become one of the most coveted seats in the city, thanks to the cafe's adventurous beverage menu (hello, mango sticky rice matcha latte!) and hyper-local event programming. Aside from piping hot coffee, Drip has been bringing a different kind of heat this summer with Hot Drip Sessions, a weekends-only DJ pop-up. August marks Hot Drip Sessions' last installment of the summer, featuring house, cumbia and afrobeat sets from locals like Aced Spade, ADONIA and more. Can't make it to West Loop? Drip Collective has been uploading past Hot Drip Sessions onto their YouTube channel. Dive into the archive here.   

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