taste of chicago, rainbow cone
Photograph: Walter S. Mitchell III, Courtesy of City of Chicago
Photograph: Walter S. Mitchell III, Courtesy of City of Chicago

The best things to do in Chicago this week

Find the very best things to do in Chicago this week, including cultural events, festivals and shows.

Shannon Shreibak
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Crashing out after a blissful holiday weekend? We can relate, but that doesn’t mean this week is a wash! September is starting off strong with festivals galore: Evanston Folk Festival, Taste of Chicago, Printers Row Lit Fest, Renegade Craft Fair and many more are taking over the weekend. For some weekday fun, catch a movie in one of Chicago’s parks, learn the art of mixology at The Happy Hour Shop or savor the views at Time Out’s favorite rooftop bar.

RECOMMENDED: Discover the best things to do in Chicago in September 2025

Time Out Market Chicago

Best events in Chicago this week

  • 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.

  • Music

What’s better than a show at the Empty Bottle? A free show at the Empty Bottle. Every Monday, Chicago’s premier indie rock club hosts a free concert. This week's bill features garage rock quartet the Ar-Kaics (think early White Stripes fuzz with deep psychedelic grooves), local surf-rock outfit Miniskirt and HoZac Sadistic Sound System.

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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.

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  • Comedy
  • Lake View

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.

  • 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 North 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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  • 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
  • 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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  • Museums
  • Grant Park

Experience the Art Institute like never before by tagging along with Marielle Epstein, assistant director of Interpretation at the Art Institute of Chicago. “Mindful Looking” is a monthly program that teaches attendees how to use mindfulness practices to enhance their museum-going experience, encouraging reflection and contemplation. A close look at an artwork is followed by a discussion and a guided meditation around a theme presented in the session. No prior experience with meditation is required.

  • 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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  • 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. Joe Flamm & Day Off Group will be manning the grill this week, and food is priced a la carte.

  • Contemporary American
  • Loop
  • price 3 of 4
  • Recommended

The rooftop restaurant and bar at the Chicago Athletic Association Hotel offers some of the best views of the city, with an expansive look at Millennium Park and the Lake. The drinks are mostly balanced, and very pretty, while the American food is also mostly well-executed and comes in massive portions and is designed for sharing.

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  • Things to do
  • Evanston

This new festival along the Evanston lakefront is a two-day celebration of folk music. The lineup features acts like Iron & Wine, Margo Price, Tune-Yards, John Moreland and The Milk Carton Kids across three stages, alongside talks with Rosanne Cash, Sam Beam (of Iron & Wine), Ann Powers and more.

  • Things to do
  • Hyde Park

Get ready to unleash your inner Nancy Drew: Escape the Museum is returning to the Griffin Museum of Science and Industry. Participants will journey through a world of mystery, where each exhibit holds clues that lead closer to victory—and the honor of being crowned a member of the Guild of Alchemists. Designed for ages eight and up, the puzzles are engaging for the whole family, while also making this a perfect outing for couples and large groups. The escape room’s runtime averages 50 to 90 minutes, though puzzle-solving prowess may shorten or extend your stay in the museum.

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  • Things to do
  • Festivals
  • Millennium Park
  • Recommended

The annual festival will feature dozens of vendors and food trucks, plus musical performances. This year's special programming includes an Eli's Cheesecake Birthday Celebration, an outdoor "Flag Feast" curated by the Design Museum of Chicago and a headlining set from Lupe Fiasco. And just like last year, the Taste of Chicago will be preceded by a series of day-long fests throughout the summer (at Albany Park, Pullman Park and Marquette Park) before heading to Grant Park for the three-day main event.

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  • Shopping
  • Markets and fairs
  • Wicker Park
  • Recommended

Renegade Craft Fair's flagship event returns to Wicker Park, taking over a stretch of Division Street spanning from Damen to Ashland Avenue. Attendees will be able to shop the handmade wares of more than 400 vendor booths, selling everything from candles and screenprints to jewelry and pottery. The fair also boasts food and drink from local restaurants, so you won't have to go hungry (or thirsty) while you shop.

When is the Renegade Craft Fair in Chicago this year?

The fall edition of the fair will be held September 6–7.

What vendors will be there?

More than 400 local artists will be at the market. Check the official website for the full list of vendors.

How much does it cost to attend?

There is a $5 suggested entry fee, which supports the Fair. You can pay by scanning a QR code at the Fair.

  • Things to do
  • Festivals
  • River North
  • Recommended

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.

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  • Musicals
  • River West/West Town

You probably know young Frenchwoman Amélie’s story from the silver screen, and now you can see it in Chicago’s intimate Chopin Theater. Transport yourself to the streets of Paris with this musical that closely follows the film’s plot—Amélie seeking connection and joy through her wondrous imagination. The musical will unfold throughout the Chopin Downstairs Studio, transforming the lobby, bar, and café into set pieces.

  • Movies
  • Loop
  • Recommended

From June through September this year, dozens of movies will screen in parks all over Chicago as part of the city's annual Movies in the Parks program. From recent blockbusters like Barbie and Wonka to classics like Black Panther and Beetlejuice Beetlejuice, you're sure to find good something to watch (for free!) beneath the stars this summer. Screenings typically begin at 8:30pm, or dusk, each evening. Take a look at the full list of movies and participating parks.

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