The best things to do in Chicago this weekend

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.

Cult favorite ice cream shop Van Leeuwen is making its Midwest debut with a new outpost in Wicker Park (1555 N Damen Ave). Oh, and it gets sweeter: You can get a taste of their limited-edition Malört ice cream, available exclusively at the Chicago shop. To celebrate opening day, Van Leeuwen is offering $1 scoops from 11am–1pm. Some extra incentive to line up early: The first 100 customers will receive a free limited-edition tote bag and other freebies. 

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.

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.

The 26th Street Mexican Independence Day Parade returns to Little Village, traversing a stretch of 26th Street. 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.

Ever wonder what kind of magic is hiding in the dreamy lofts along Ravenswood Avenue? Now's your chance to find out. Take a stroll through the 23rd annual Ravenswood ArtWalk 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. 

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.

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 and Mary Lattimore, with some special sets curated by Electrical Audio—the recording studio founded by the late Steve Albini. Read more about Sound & Gravity's inception here.

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 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.

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. 

Sunday! Sunday! Sunday! Actually, this festival of revving engines takes place throughout the weekend. Colossal trucks slam, crush and perform stunts as cheesily entertaining as any wrestling match. The world’s best drivers tear up on the dirt as they battle for the Event Championship in four competitions: Racing, Skills, Donuts and Freestyle. Arrive early on Saturday or Sunday for the Monster Jam Pit Party, where families can get up close and personal with the massive trucks, snap a selfie, meet their favorite drivers and collect autographs.

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.

As if you needed an excuse to spend golden hour at Time Out Market'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.

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 well into the night.

Chicago's beloved button company Busy Beaver is celebrating 30 years in business with a shindig at Color Club. The event will include live music from Detroit-based garage rock outfit The Henchmen, local lo-fi noisemakers Sharp Pins and more. Attendees can also hop into a Double Dutch match, make their own buttons and sip on signature cocktails from Wilderness Club. Proceeds from the event will benefit the Greater Chicago Food Depository. 

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.

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.