Two people play a game of carnival-style Bulls-themed basketball
Photograph: Jesus J. Montero
Photograph: Jesus J. Montero

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Shannon Shreibak
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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, the Chicago Triathlon—predicted to be the largest in the city's history—blazes across Chicago. For the basketball fans out there, Bulls Fest returns to the United Center grounds with a 3v3 basketball tournament, food trucks, dunk contests and more. For a more low-key weekend, swing by Taste of Greektown or find your groove at the annual Chicago House Music Festival and Conference.

RECOMMENDED: Discover the 50 best things to do in Chicago right now

Time Out Market Chicago

Best events in Chicago this weekend

  • Things to do
  • Festivals
  • Greektown

Enjoy feta, tzatziki, roasted chicken and more signature Mediterranean flavors at this three-day festival in Greektown, where you'll find lots of tasty dishes cooked by some of the neighborhood's most beloved restaurants. Stick around for performances from Greek and American bands. Opa!

  • Things to do
  • Markets and fairs
  • West Loop

Time Out Market Chicago's Market Shop returns with a brand-new theme! This season’s “Summer Reset Edition” combines a wellness-inspired market with a special movement class. Enjoy a curated mix of wares from local businesses and wellness brands focused on beautiful design and intentional living. Follow up your shopping spree with a Fusion Movement class and sound bath (tickets required).

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  • Music
  • Music festivals
  • Loop
  • Recommended

This annual fest and conference celebrating the iconic dance music genre born in Chicago brings a full day of DJ sets to Millennium Park. Acts this year include Ralphi Rosario, Specter, Psycho B, Shaun J. Wright and more. The live music will be preceded by an open house and panel discussions, and the festival will wrap up with a chill-down session along the Riverwalk. 

  • Things to do
  • North Side

This year's Chicago Triathlon is set to be the largest in city's history, so you best be competing or watching. Swim, bike and run along the lakefront during the Chicago Triathlon, which starts at Montrose Harbor before zooming down Lake Shore Drive and finishing in Grant Park. There are different courses for athletes of all levels, spanning 32, 18.5 and 8 miles, as well as races for kids ages 14 and under.

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  • Art
  • Film and video
  • Recommended

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 8:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Things to do
  • Festivals
  • United Center

The Chicago Bulls' beloved Bulls Fest returns for another year, bringing a 3v3 basketball tournament, food trucks, dunk contests, live music, an art show and more basketball-themed programming to the United Center campus. You'll be able to attend skills clinics and check out games from the 3v3 tournament—which will host teams of all skill levels ages eight and abovethroughout the day. Plus, visit the United Center South Atrium to tour "The Art of the Game," an immersive art exhibition featuring artwork inspired by the Bulls. 

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  • Things to do
  • River West/West Town

Infatuation is bringing back EEEEEATSCON, the two-day food festival corralling some of the city’s best restaurants under The Salt Shed's roof for Chase Sapphire Reserve and Preferred cardholders. The weekend's programming is rounded out with special guest appearances from Joe Freshgoods, Lyrical Lemonade, Celebrity Memoir Book Club (in conversation with special guest Shea Couleé) and more. Participating eateries include Kanin, Dayglow, Motorshucker, Taqueria Chingón and more.

  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • Recommended

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 N Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levelsyou just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

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  • Things to do
  • Markets and fairs
  • Logan Square

In collaboration with local photographer Clayton Hauck and photo book pop-up shop Realm, Parson's has wrapped two unique photography experiences into one whirlwind day. Hauck will be offering free photobooth portraits in the style of his distinctive "Keep it 100" series, which utilizes rotating backdrops and lighting schemes to yield a wealth of one-in-a-million results. For the collectors out there, Realm—which was co-founded by Hauck and fellow photographer Jack Garland—will be slinging books and zines from photographers around the world.

  • Things to do
  • West Loop

Enjoy an afternoon of glitz, glam and drag at Time Out Market Chicago! Local queens Aurora Gozmic, Vanda LaRose and Ari C. Blakk Diamond are ready to bring you an unforgettable afternoon filled with jaw-dropping performances and dazzling costumes. The show is free to attend and a full bar—including bottomless mimosas and every type of cuisine—will be available for purchase.

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  • Things to do
  • West Loop

As if you needed an excuse to spend golden hour at Time Out Market Chicago's rooftop bar—we're hosting a very special happy hour until the cold snap arrives. Sip on vibrant spritz drink specials crafted for summer lounging, complete with a live DJ spinning feel-good vibes all evening long. Whether you're here to dance, chill or just toast to the moment, this is your chance to savor the season.

  • Ukrainian Village

Sportsman's Club's backyard BBQ series is back for another glorious year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. This weekend, Joe Flamm & Day Off Group are behind the grill.

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  • Comedy
  • Uptown
  • Recommended

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

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  • Things to do
  • Quirky events
  • Irving Park

Making Chicago summers even cooler: The Sugar Hole, an ice cream hut on the grounds of the multidisciplinary arts venue Color Club—staffed entirely by...puppets? When The Sugar Hole opens up shop, a rotating cast of puppets pops through a black porthole to take customers' orders and cause general mayhem. Along with soft serve and Pretty Cool Ice Cream offerings, The Sugar Hole serves up soda, coffee and beer.

  • Things to do
  • Classes and workshops
  • River West/West Town

Mix, stir and shake your way toward speakeasy-worthy cocktails with hands-on guidance from the founders of Aged & Infused, a Chicago-based alcohol infusion kit company. During each workshop, you’ll build two cocktails from scratch using stunning barware plucked from the shop floor. Spirit tastings will be offered throughout the night, leaving time to sip and savor between recipes. If you’re not in the mood for a boozy night out, non-alcoholic substitutes are offered for each cocktail.

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  • Experimental
  • Uptown

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

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  • Things to do
  • Exhibitions
  • Suburbs

With its latest exhibition, the Chicago Botanic Garden showcases the patterns and prints that adorn the natural world. Through meticulously planted gardens and nature-inspired art installations, Patterned by Nature highlights the intersection between graphic design and horticulture. Exhibition highlights include colossal embroidered flowers by Raquel Rodrigo, a collection of upcycled fashion sourced from garden materials by Columbia College Chicago’s School of Fashion and a paisley patterned succulent garden. 

  • Things to do
  • West Loop

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 acrobat sets of 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

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