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Chicago Marathon 2016
Photograph: Max Herman

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Jeffy Mai
Edited by
Jeffy Mai
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Welcome to another weekend! Fall has arrived and if you're looking for an adventure outside of the city, go hiking or apple picking in the suburbs. Here in Chicago, you can get in the spooky spirit with Halloween-themed events, attend a beer or wine festival, or cheer on thousands of runners during the Chicago Marathon. So ready to make the most of your time off? Check out the rest of the best things to do in Chicago this weekend.

RECOMMENDED: The best things to do in Chicago right now

Events and to do this weekend in Chicago

  • Things to do

This festival honoring and amplifying the voices and contributions of Indigenous peoples will take place at Wicker Park's Chop Shop over two days. Attendees will be able to immerse themselves in Indigenous music from Canada, the United States and Latin America, with performances by Digging Roots (Canada), Keith Secola (USA), Novalima (Peru), OPLIAM (USA), Raye Zaragoza (USA) and more. There will also be various engaging activities, craft demonstrations and interactive workshops. Admission is free but guests are encouraged to reserve their tickets online.

  • Things to do
  • Festivals
  • River West/West Town

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. 

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  • Things to do
  • Quirky events
  • Wrigleyville

Hosted at tropical bar Bamboo Club, this annual Halloween-themed extravaganza features a multi-level haunted house as well an upstairs bar serving spooky cocktails. Tickets for the haunted house (which is open to attendees ages 16 and older) are $20 or $30 for VIP, which includes a drink and express entry.

  • Things to do
  • Festivals
  • Suburbs

Round up your family for a wild, multi-weekend Halloween festival perfect for all ages to enjoy. Decorate a pumpkin, take a spin on the decked-out carousel or pose for photos amongst giant inflatables and wooden cut-outs of Halloween characters. The not-too-spooky event also treats some of the zoo's animals—including capybaras, polar bears and gorilla—to pumpkins that they can play with, nibble on and smash. 

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  • Theater
  • Comedy
  • Lincoln Park

Test your knowledge of all things holy and haunted during Holy Ghost Bingo: God, Goblins & Games, an interactive comedy bingo show at the Greenhouse Theater where audience members get quizzed on Halloween and Catholic traditions alike. FYI: You'll actually be playing bingo for this one, so Halloween candy and other spooky prizes are yours for the taking. 

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  • Things to do

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 Millie Bobby Brown, Keegan-Michael Key and Elle Key, Bob Odenkirk and Henry Winkler. You can see a full schedule of programming on the Chicago Humanities Festival website

  • Theater
  • Loop

Hamilton, writer-composer-lyricist Lin-Manuel Miranda’s biography of Alexander Hamilton as refracted through a hip-hop, pop and R&B lens, is a sprawling, stunning, singular achievement. It returns to Chicago for another run this September through December. Check the official website for the full schedule.

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  • Things to do
  • Loop

Based on the family-favorite board game, this new immersive and interactive experience puts guests into the roles of beloved CLUE characters as they try to solve a murder mystery. The game starts at Block 37, where detectives are greeted by the Butler before being sent on their way to gather clues from popular Chicago sites and shops. You’ll be tasked with finding long-lost antiques and figuring out who did it, where and with what.

  • Music
  • Jazz

The South Side Jazz Coalition is hosting a series of free monthly jazz performances this summer on the steps of the St. Columbanus Catholic Church in Greater Grand Crossing. Bring a lawn chair, some snacks and prepare to hear some top-notch music from the Chicago jazz community—plus, every performance ends with a jam session. 

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  • Things to do
  • West Loop

Put on your best pink attire and let your nostalgia run wild at this pop-up inspired by the iconic doll. Fans will enjoy all-day brunch fare from Master Chef semi-finalist Becky Brown and sip on refreshing cocktails while hanging out on a breezy, beach-themed patio. There are plenty of photo ops—including a life-sized Barbie box—plus exclusive merch to pick up. You can even strap on roller skates and glide around an outdoor rink!

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  • Shopping
  • Markets and fairs
  • West Loop

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) every Sunday, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

  • Sports and fitness
  • Yoga & Pilates
  • Streeterville

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 levelsyou just need to bring your own mat and arrived properly dressed. Registration is $50 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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  • Art
  • Film and video

Displaying a 25-story-tall video installation on the side of the Merchandise 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. It’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Comedy
  • Sketch shows
  • Lake View

Bye Bye Liver combines two robust Chicago traditions: comedy and heavy drinking. The show opened a decade ago for a three-week run, then kept getting extended. A cast of four to six performers portray characters at the fictional "Franks Bar," telling stories that explore the city's robust drinking culture. Each show incorporates interactive audience drinking games, allowing you to sip a cocktail or beer while taking cues from the cast. And if you're up for a nightcap after the performance, you can stick around for the official after party and mingle with the cast.

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  • Nightlife
  • Cabaret and burlesque

Settle in for an evening of burlesque performers, belly dancers, drag artists and variety entertainers during this weekly show at Newport Theater. The hour-long show features speciality cocktails and intimate seating arrangements, making this feel like a clandestine speakeasy experience. Bring some singles so that you can tip performers throughout the night!

  • Theater
  • 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. Returning to in-person programming (attendees must be vaccinated and masked) after more than a year spent in the virtual realm, the company's signature show is more unpredictable than ever, 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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  • Comedy
  • Uptown

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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