Chicago October 2026

Chicago October 2026 Events

Chicago October 2026 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

Chicago Events in October

Concerts

Theater & Headliners

Sports

Nightclubs

Things to do in Chicago

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.