The best things to do in Chicago this week

Ever wonder what kind of magic is hiding in the dreamy lofts along Ravenswood Avenue? Now is your chance to find out. Take a stroll down Ravenswood Avenue to see art, live music and theater at this local festival centered around the neighborhood's industrial corridor, showcasing dozens of artists and local venues including Begyle Brewery, Lillstreet Art Center, Koval Distillery, VIN312 Winery and more. This year—the festival's 23rd—swing by the outdoor beer garden for local brews and food trucks, or listen to some live tunes across two stages.

Local no-kill animal shelter PAWS hosts its annual 5K race at Montrose Harbor, where humans and dogs can make their way through a lakefront course while raising money to support the organization's work. Once you cross the finish line, you'll be able to enjoy live entertainment for humans and pups alike, including a dog agility course and a "doggy oasis" outfitted with pools for cooling off. Don't have a four-legged friend to bring along? Not to worry—there will be plenty of good boys and girls for you to pet.

The 26th Street Mexican Independence Day Parade returns to Little Village, traversing a stretch of 26th Street ahead of Mexican Independence day on September 14. The theme of this year's procession—which includes mariachi bands, colorful floats and folkloric dancing—is “Pride and Power: Our Strength, Our Legacy,” focusing on the heritage and resilience of the Mexican community. The parade runs between Albany and Kostner on 26th Street.

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.

Chicago's Guinness Brewery outpost is raising a stein to fall with an Oktoberfest celebration. The three-day event will feature live music, Bavarian-inspired food specials, exciting giveaways and contests and exclusive in-house Oktoberfest beers brewed just for the season. Guests can enjoy performances by The Dirndls and The Rhinemaidens, alongside classic Oktoberfest traditions—like stein-hoisting competitions—and Bavarian bites including schnitzel, giant pretzels and sausages.

The Irish American Heritage Center hosts its annual Halfway to St. Patrick’s Day celebration, featuring four days of food, drinks, live music and Irish dancing. This family-friendly celebration will also offer face painting, outdoor games and plenty more activities to keep the Irish spirit alive all weekend long. The entertainment lineup includes Irish dancers, a bagpipe and drum outfit, classic Irish folks singers and more.

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, as well as a whole stage curated by Electrical Audio.

Wanna relive the thrill of punishing a captive audience like you did during grade school show-and-tell? Then Show & Tell for Grownups is the place for you! Once a month, comedians, storytellers and everyday passionate folks gather to share their quirky, heartfelt or downright fascinating interests. Each presenter gets five minutes on the clock to wax philosophical about their obsession, then it’s the audience’s turn with a quick Q&A. Think of it like falling down a Reddit rabbit hole—only live, and way more fun.

Cap off your summer with a breezy drink on the beach! Indulge in mixologist-crafted cocktails inspired by tropical climes while enjoying beachfront views. Whether you're a Mai Tai connoisseur or a casual imbiber, Tropical Cocktail Fest is sure to satisfy any palate. A ticket fetches you three hours' worth of cocktails, photo ops and more.

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.

Take a look at art from more than 120 juried artists at this annual event in Lakeview East, where you can also catch live music. Visit a variety of food and drink booths when you get hungry, or head over to the Kidzone to entertain little ones with origami demos, circus performances, live music and other attractions. The fest, which stretches along Broadway from Belmont to Hawthorne, goes until 7pm on Saturday and Sunday—though live music goes into the night.

Inspired by the cultural resurgence of Mort Garson’s synth-powered album Mother Earth’s Plantasia, Empty Bottle Presents and Sacred Bones Records have been hosting an annual music festival celebrating plants and people who love them for nearly half a decade. Spread across two days, attendees can enjoy experimental music and on-site activations in the Garfield Park Conservatory's lush confines. This year's lineup includes electronic music legend Suzanne Ciani, ambient juggernaut Tim Hecker, Pakistani composer Arooj Aftab and more.

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.

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.

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.

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. 

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.

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.

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.

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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