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

  • 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.

  • 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
  • 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.

  • 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.

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  • 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.

  • 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. 

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  • 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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