Everything You Can Do in Chicago This Weekend

Fall is kicking into high gear.

Well, it’s starting to feel a lot more like fall out there, Chicago. Which means while your outdoor options are steadily becoming more limited, there’s still plenty of virtual fun to be had this weekend from cemetery races to pork festivals to club parties. Those itching to get out and about can also enjoy Halloween-themed movies, costume contests, art exhibits, and even real-life in-person concerts. Here’s everything fun you can do in Chicago this weekend.

Get 'toasted' at Chicago’s first Cheba Hut

Now Open
1948 W. Division
Chicago continues to boost its stoner food bona fides as national marijuana-themed sub franchise Cheba Hut opens its first Illinois location in Wicker Park, one of six planned locations in Chicago. Stop by for “toasted subs” alongside a variety of munchies including Rice Krispy treats and a full-service bar slinging local brews plus cocktails such as The Dirty Hippie and Hot Box. Appetizers, anyone?
Cost: Depends what you order

Pig out (virtually) at Carry Out with Cochon555

Now through Saturday
The annual pork-centric touring food festival makes a stop in Chicago this week, with local chefs from Frontier, River Roast, Purple Pig, and more hosting virtual dinners on Zoom along with cocktails, wine, and chef demos. The multi-course meal, featuring pork sourced from local heritage breed pig farms, is available for pickup or delivery.
Cost: $100+  

Run through the cemetery (virtually) as part of the Crypt Run

Now through October 31
America’s largest cemetery run has gone virtual for 2020 during the month-long Crypt Run, where you can design your own course through Lincoln Park, Ravenswood, or wherever the hell else you feel like running -- with plenty of Halloween swag for participants to show off on their run.
Cost: $30 

Explore the spiritual side of Halloween during Day of the Dead: A Celebration of Life

Now through November 14
The Art Center Highland Park
Halloween wouldn’t be Halloween without a Dia de los Muertos exhibit. With the National Museum of Mexican Art still closed, your best bet is to head up to Highland Park to check out their free exhibit entitled Day of the Dead: A Celebration of Life.
Cost: Free

Sip fancy drinks during the Mixology & Full Cocktail Sampling Experience

Friday 6pm
Hubbard Inn
This two-hour mixology experience will have you learning and sampling three of Hubbard Inn’s top craft cocktails alongside hors d'oeuvres and a bottle of hard seltzer.
Cost: $50

Bring your pup to the Ruff Haus Halloween Pet Costume Contest

Saturday Noon
Ruff Haus Pets
Who couldn’t use a healthy dose of cuteness right about now? Get your fix at the annual Halloween Pet Costume Contest at Ruff Haus Pets, where your pet will get photographed to post on Instagram in advance of online voting which ends October 30.
Cost: $20 donation 

Go clubbing (from your couch) with CCTV: Chicago Club Television

Saturday 6pm
Chicago Club Television (CCTV) aims to broadcast local party collaborations with different local DJs every Saturday night in an effort to “bring the nightlife scene into your living room.” Best stock the fridge with Red Bull and vodka, at the very least.
Cost: Free-$10 

Rock a socially distanced funk fest with JC Brooks at City Winery

Saturday 7pm
City Winery
Live music returns to City Winery with local funk legend JC Brooks hosting an in-person performance, as the venue is set up for “social distance seating.” The show, as they say, must go on.
Cost: $25 for tickets (plus $40 requested minimum food/beverage purchase per person) 

Do your best hippie twirl at Terrapin Flyer’s 21st Anniversary Show

Saturday 7:30pm
Schaumburg Boomers Stadium
Local Grateful Dead cover band Terrapin Flyer host this drive-in anniversary show at Schaumburg Boomers Stadium. Will the parking lot smell like weed? What do you think?
Cost: $100-$160 per carpool 

Get an overdose of Halloween movies at the Chicago Drive In

NOW Arena
NOW Arena (formerly the Sears Centre) hosts more drive-in Halloween movies than you can handle this weekend with five classic screenings including Ghostbusters, Halloween, and Nightmare on Elm Street as part of its Chicago Drive In series.
Cost: $35-$55 per car per movie

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.