The best things to do in Chicago this week

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 at 9pm and Saturdays at 10pm) 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.

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!

Put your thinking caps on and get ready to test your knowledge: Time Out Market is hosting Whaddayaknow Trivia every Wednesday! Whether you're a trivia master or just looking for a good time, this event offers something for anyone and everyone...and it's no coincidence that this evening of brain flexing falls on Wine Wednesday, when Time Out Market offers 50% off all bottles of wine.

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 above—throughout 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. For a full schedule of events and programming, visit the Bulls Fest site. 

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. For a full list of programming, visit the DCASE Chicago House Music Festival and Conference website.

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.

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.

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.

The oldest music festival in North America plays host to more than 100 shows throughout summer, featuring big-name headliners like Janelle Monáe, Lenny Kravitz and James Taylor. Check out the full schedule of artists coming to Highland Park this year and don't forget to pack a picnic.

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.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

Enjoy outdoor live music all summer long at the Navy Pier Beer Garden. The free series will feature local, regional and national acts performing countless genres and musical styles every weekend. Check the official Navy Pier website for the full lineup and schedule.

Humboldt Park transforms into an outdoor tapas bar during this boozy bash, which pairs bites from local restaurants with pitchers of red wine and chopped fruit. Lay our a blanket to sip sangria on the lawn, put color on a canvas at the festival's painting station or watch live salsa and Brazilian dance music.

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.

Before it was shut down by the city in 2024, the Humboldt Jungle was a DIY operation hosted in founder Nathan Weil's Humboldt Park basement. Comedians, musicians and audience members would pile into the subterranean space to enjoy live entertainment and a few slices of pizza. Since it was forced to leave its original digs, the Jungle has reemerged as a traveling variety show, popping up at venues across the city. Oh, and there's still pizza—this time catered by Professor Pizza.

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.

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).

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. Check the website for a schedule of upcoming performances and to RSVP.

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.

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.

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.

Macy's opulent and iconic Walnut Room hosts a drag brunch dedicated to pop girlies Sabrina Carpenter, Chappell Roan and Charli XCX. Hosted by local queen Lucy Stoole, the event will feature performances by RuPaul's Drag Race's Aquaria, Bambi Banks-Couleé and Opal Cavalli. Upgrade to VIP to meet the artists.

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.

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.

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.

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.

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 levels—you 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.

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. 

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