Chicago October 2021 Events

Chicago October 2021 Events

Get in the Spooky Spirit and Check Out Halloween-Themed Events in Chicago

Average temperature low and high: 50°- 62°
From Nightmare on Chicago Street, to the Haunted Halloween Ball, Chicago has lots of cool events in celebration of Halloween time to check out. There are also cool culinary events throughout the month to help you explore this food focused-city; check out the Cantigny Food Truck Festival or the Chicago's Taste of a Nation event. Whatever you decide, the October calendar if filled with fun options.

October Event Calendar

Open House Chicago

Open House Chicago

Every year when October comes around, the Chicago Architecture Center hosts a free 2-day festival open to the public. Open House Chicago focuses on highlighting and exploring over 250 of Chicago's most significant places with behind-the-scenes access. Attendees will get to see historic mansions, private clubs, sacred spaces, hotels, offices, theaters, and more. There will also be other virtual events throughout the month. 

Bruce Bruce

Bruce Bruce

Bruce Bruce is no stranger to the entertainment industry. From his role as host for two seasons of BET's Comic View to his role in the comedy Who's Your Caddy as "Golf Ball Eddie." His hilarious improv skills will have you clenching your stomach and laughing all night. Don't miss out; purchase your tickets here.

Halloween Day Crawl

Halloween Day Crawl

No need to wait for trick-or-treating hours to celebrate Halloween. Start things off early in River North at the Halloween Day Crawl. Starting at 11am, join others dressed in costumes hop from one bar to the next. Tickets include a free brunch buffet, gift cards to use on the crawl, a costume contest, giveaways and more. Tickets are available online.

Haunted Halloween Ball

Haunted Halloween Ball

Lavish VIP nightclub meets eerie haunted house at the annual Halloween Ball. Twenty thousand square feet of a 120+-year-old hotel (The Congress a Hotel), known as one of the most haunted hotels in the world, will transform into an abandoned hotel operated by zombies. Put on your best costume and dance the night away! The ball will feature a great DJ, theatric performances, and a costume contest with a $2,000 prize. Early bird general admission is $20. VIP tables and group discounts will also be available.

See what's happening in Chicago Today
Chicago Today

Chicago Events in October

Concerts

Theater & Headliners

Sports

Nightclubs

Upcoming events

Fri, Oct 01 at Schubas Bailey Bryan
Fri, Oct 01 at Lincoln Hall Men I Trust
Fri, Oct 01 at Schubas Couch
Fri, Oct 01 at PRYSM Joel Corry

Things to Do in Chicago in October

Try a Chicago Italian Beef Sandwich

Try a Chicago Italian Beef Sandwich
Slices of roasted sirloin cooked in a seasoned broth and stuffed inside an Italian-style roll, the Italian beef sandwich is a Chicago staple that's a must-try when in town. There's no debate about who has the best one, make sure you stop by Al’s Italian Beef’s for this mouth-watering sandwich. You won't regret it.

Visit Old Fashioned Candies

Visit Old Fashioned Candies
Get your sweet fix at this nostalgic candy store that has been open since 1969. This family-run business hooks locals and visitors with their handmade chocolates and penny candies. They even sell supply kits to take with you to make your own candy at home.