The best things to do in Chicago this week

Chicago Gourmet, the annual food festival hosted by the Illinois Restaurant Association, returns this year with a four-day slate of programming and events in celebration of the city's dining scene. Nosh on a variety of delicious bites and sip wines at events like Tacos & Tequila, Hamburger Hop, Grand Cru and the brunch-centric Rise & Shine Gourmet. 

Taking place in and around Lakeview’s St. Alphonsus Church, this autumn fête features the requisite selection of suds, brats, pretzels and two stages of Bavarian music (along with sets from cover bands). Activities include a stein-holding contest, polka dancing and a “Kinderfest” for the kiddos on Sunday. 

Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 

Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. 

Get your fall feels on at Lincoln Park Zoo's annual free festival. You can snag a photo with a giant pumpkin, watch master carvers at work, enjoy live music and see all kinds of animals. The festival also includes several ticketed experiences such as carousel rides, a bounce house, harvest maze, a slide and more. 

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. 

Every year, 2,000 people show up and show out at the largest HIV gathering in the Midwest to raise funds for AIDS Foundation Chicago. The event encourages the Chicagoland community to show up and show out as their most authentic selves to mobilize support for those living with HIV/AIDS.

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.

Founded in 1981 and organized by Chicago Filmmakers, Reeling is the second-oldest LGBTQ film festival in the U.S., featuring a lineup of features, shorts and documentaries highlighting the diversity of queer stories and filmmakers from around the world. The fest will show dozens of feature and short films this year in a mixture of in-person and virtual screenings.

In celebration of Hispanic Heritage Month, Renaissance Chicago Downtown Hotel is hosting a pop-up market full of Chicago businesses in its elegant lobby. Vendors include Latina-owned wine shop Vinoteca, Sprinkle Candles, Celeste's Flower Shop and more.

The Hyde Park Jazz Festival returns to venues throughout its namesake neighborhood in September. As always, Hyde Park Jazz Festival's shows are free to attend. This year's lineup includes rising star Lily Finnegan's Heat On, Jason Moran's celebration of Duke Ellington, influential Chicago percussionist Hamid Drake and more. For a complete list of performances, visit the festival's website.

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city just in time for spooky season. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, more than 10,000 pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket nets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing. 

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.

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of this season's biggest speakers include Kate McKinnon, Margaret Atwood, Salman Rushdie and Nick Offerman. 

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.

Prost! to Oktoberfest at Brookfield Zoo Chicago, where their Carousel Plaza will feature family-friendly fun with polka music, dancing, games, giveaways and more. This German-style event is included with Zoo admission and will feature a special seasonal menu with bratwurst, specialty beers, pretzels with cheese and more available for purchase.

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.

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