some like it hot
Photograph: Matthew Murphy
Photograph: Matthew Murphy

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
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Welcome to another weekend! Find the best things to do in Chicago this fall before winter is upon us. The Chicago Pizza Summit returns on Sunday, offering attendees the opportunity to feast on all the slices they want, while espresso martini lovers can head to Hubbard Inn for a fest dedicated to the alcoholic drink. You can also get a head start on holiday shopping at Sauced Night Market, climb up the Willis Tower during SkyRise Chicago or take part in a 5K with the Hot Chocolate Run. 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

Time Out Market Chicago

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market featuring more than 15 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.

Best events in Chicago this weekend

  • Things to do
  • Quirky events
  • Wicker Park

There's no need to debate about which city has the best pizza in the world because nine out of ten Chicagoans agree that ALL pizza is delicious. The Chicago Pizza Summit celebrates thin crust, deep dish and everything in-between with an all-you-can-eat event at Royal Palms Shuffleboard, where attendees can dig into pies from Professor Pizza, Gino's East, Bacci, Zazas, Paper Plane and other slice purveyors. The festivities will also include a special keynote speaker, a pizza tattoo parlor and a pizza pop-up art showcase. There will be two sessions, and admission comes with five drink tokens.

  • Things to do
  • Markets and fairs
  • Lincoln Square

SAUCED celebrates its 10th anniversary with a night market at Half Acre, where over 50 local vendors will be selling handmade goods, jewelry, vintage clothing, prints and more treasures. Need to refuel? Snag food from local eateries like Soul & Smoke, Fat Shallot and Bumbu Roux, or bust some moves to live beats from DJ Johnny Walker.

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  • Sports and fitness
  • Running
  • Millennium Park

What's the ultimate reward for finishing a 5K or 15K race? If you answered "chocolate," then you should probably sign up for the Hot Chocolate 5K, 10K, 15K or two-mile walk, an annual race that lets participants indulge in all types of sweet treats once the running is over. Participants get a race-themed hoodie, a medal the looks like a cup of hot cocoa and access to post-race gathering where the chocolate goodies will be served.

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  • Things to do
  • River North

Can’t get enough of espresso martinis? Then head to Hubbard Inn, where you can sample 15 different concoctions during an event celebrating the caffeinated cocktail. There will be giveaways, good vibes and more.

  • Things to do
  • Loop

The annual SkyRise Chicago challenges participants to climb the Willis Tower in support of the Shirley Ryan AbilityLab, a non-profit physical medicine and rehab hospital. That means you’ll have to go up 2,149 stairs (105 flights). Can’t make it in person? Participate virtually by walking or running 6,327 steps or cycling 3.2 miles.

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  • Things to do
  • Bridgeport

Vinyl & Vittles is back for another year. The event brings together a host of record vendors for a day of music and fun. You can peruse through crates of vinyl, enjoy delicious bites from food vendors and dance to tunes spun by local DJs.

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  • Loop

Winner of four Tony Awards, Some Like it Hot makes its way to Chicago for a two-week run at the Cadillac Palace Theatre. The musical tells the story of two musicians forced to flee the Windy City after witnessing a mob hit. With gangsters hot on their heels, they catch a cross-country train for the life-chasing, life-changing trip of a lifetime.

  • Things to do
  • Suburbs

This new exhibition from Chicago Gamespace and the Cleve Carney Museum explores the history of legendary Chicago video game company Midway and its rise to prominence in the ‘90s. Take a look at behind-the-scenes videos, interviews with former game designers, and art, or try your hand at any of the 15 playable arcade games. Midway’s celebrated legacy includes hits like NARC, Smash TV, Terminator 2, Mortal Kombat, NBA Jam and Cruis’N USA.

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  • Time Out Market
  • West Loop

Celebrate the Mexican holiday at Time Out Market Chicago with a full day of family-friendly activities on November 2. Bring the little ones for storytelling with Mirabel at 11am, followed by sugar skull face painting. The Market will have sugar skull decorating kits for purchase, a live mariachi band and Dos Hombres Mezcal samplings in the afternoon. A live DJ will close things out from 7-10pm.

  • Cocktail bars
  • Lincoln Park

Spooky season will get a bit boozier this year thanks to this horror-themed cocktail pop-up at the Albion Manor, where Halloween lovers can sip expertly mixed cocktails amid metal music and goth decor. Drinks are imbued with playful touches and include choices like Frank's Fix (vodka, carrot, miso falernum, coconut, sherry, lime, five spice bitters) and Nightmare Fuel (tequila, mango liqueur, matcha, lime, Thai spice bitters, absinthe). Want to recreate the creepy vibe at home? Several of the drinks are served in Halloween glassware that’s available for purchase onsite.  

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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) start at $15, or $23 for GA+, which includes a drink and express entry.

  • Things to do
  • Streeterville

Iconic chocolate brand Hershey has brought its first-ever immersive attraction to Water Tower Place, transporting guests to a whimsical, real-life candyland. Upon entering the indoor play experience, guests will explore various themed zones to discover what makes Hershey treats so special. From navigating a Twizzlers maze to celebrating the perfect combination in Reese’s Peanut Butter Cups, it’s family-friendly fun that tugs at the heartstrings. Plus, when you’re finished, stop by the retail store to snag limited-edition merch.

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  • 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. 

  • Things to do
  • West Loop

Come join us at Time Out Market Chicago during football season to catch the Bears in action on the big screen. We'll be showing the games—with sound—each week on a 32 feet wide by 6 feet tall screen, and you can chow down on a variety of delicious eats like fried chicken, burgers and tacos while sipping a cold beer or cocktail. So gather the crew and cheer on the Bears!

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  • Loop

The six-time Tony Award-winning production kicks off its national tour with a five-month run in Chicago. Nineteen years after Harry, Ron, and Hermione saved the wizarding world, they’re back on a most extraordinary new adventure—joined by a brave new generation, including Harry’s son Albus—that threatens to change the past and future forever. The play has sold over 10 million tickets worldwide since its world premiere in London in July 2016, and holds a record 60 major honors.

  • Things to do
  • Loop

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, Ketanji Brown Jackson, R.L. Stine and Connie Chung. You can see a full schedule of programming on the Chicago Humanities Festival website

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  • Things to do
  • Hyde Park

The Griffin Museum of Science and Industry has debuted an exhibit dedicated to the science and technology behind the world’s longest-running film franchise, James Bond. Fans can check out 13 vehicles and over 90 additional artifacts, including the prototype jetpack used in Thunderball, an MI6 Retina Scanner from GoldenEye and the Parahawk snowmobile hybrid from The World Is Not Enough. You’ll also be able to step into a lab space inspired by “Q” and test your skills developing the perfect vehicle for spy activities, designing stunts and more.

  • Things to do
  • Skokie

The largest and most immersive touring Titanic exhibition has come to Westfield Old Orchard mall in Skokie. Visitors will experience a narrative journey that brings to light the fates of the passengers and crew aboard the famous ship. Marvel at hundreds of artifacts that survived the sinking, plus props and costumes featured in James Cameron’s blockbuster film Titanic. Music from the era plays as patrons walk through detailed recreations of the ship’s interiors, including the grand staircase, while the Discovery Gallery simulates what discovery teams saw during dives to the Titanic’s wreckage site.

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  • Things to do

One of Navy Pier’s newest attractions transports guests to some of Chicago’s most epic places via exhilarating flights. The multi-sensory experience incorporates drone technologies with aerial shots and first-person views to showcase the city like never before. Guests will swoop, dip and turn in motion seats as they climb up skyscrapers, check out iconic landmarks, float through fireworks and more.

  • Art
  • Film and video

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. It’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

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  • 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 $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.

  • Things to do
  • Markets and fairs
  • Lincoln Park
Green City Market Lincoln Park
Green City Market Lincoln Park

One of Chicago's most popular farmer's markets, Green City Market welcomes vendors selling regional produce to the south end of Lincoln Park (between Clark Street and Stockton Drive) on Wednesdays and Saturdays. Amid the rows, you’ll find farm-fresh eggs from Michigan, cheese from Wisconsin and scrumptious pies baked by Chicago’s own Hoosier Mama Pie Co.

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  • Comedy
  • Sketch shows
  • Lake View

Bye Bye Liver combines two robust Chicago traditions: comedy and heavy drinking. The show opened over 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.

  • Experimental

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.

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  • Comedy

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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