Find the best things to do in Chicago on Pelago. Plan and book online with the best prices and world class support.

The Best Things to Do in Chicago | Updated December 2025

Chicago

Experience Shakespeare like never before as a whiskey-fueled actor brings humor and chaos to the stage in this unique spin on classic theater in Chicago.

drunk-shakespeare-ticket-chicago_1

Prepare for an evening of laughter and astonishment at Trickery Chicago Magic Show where clever illusions and a lively audience create unforgettable moments in a cozy setting. Enjoy your BYOB experience!

trickery-chicago-magic-show_1

Experience the joy of crafting sushi rolls perfecting your knife skills and engaging with fellow food enthusiasts in a fun and interactive environment in Chicago.

from-rice-to-roll-2-hour-sushi-making-class-in-chicago_1

chicago-delicious-donut-adventure-by-underground-donut-tour_1

Savor iconic Chicago-style hotdogs while exploring the city's rich food history. Experience hidden gems and famous eats all while discovering downtown landmarks and enjoying a unique culinary adventure.

chicago-favorites-food-walking-tour-with-bike-or-kayak-rental_1

chicago-in-a-day-food-history-and-architecture-walking-tour_1

Savor iconic Chicago bites while surrounded by vibrant conversations and local charm highlighting the city's rich culinary history and engaging culture. Each dish tells a unique story.

chicago-walking-food-tour-with-secret-food-tours_1

bikes-bites-and-brews-chicago-s-signature-dishes-bike-tour_1

chicago-s-chinatown-food-and-walking-tour_1

chicago-pizza-tour_1

haunted-chicago-booze-and-boos-ghost-walking-tour_1

downtown-chicago-walking-pizza-tour_1

chicago-small-group-food-tour_1

Experience the charm of the Christkindlmarket where delightful treats like roasted nuts and gingerbread fill the air creating the perfect backdrop for a memorable holiday escape in Chicago.

Get 10% off on the app with promo code APP10

The Best Things to Do in
Chicago

Drunk Shakespeare Ticket - Chicago

Trickery Chicago Magic Show

Sushi Making Cooking Class at a Local Distillery in Chicago

Delicious Donuts & City Sights: Chicago's Original Donut Tour

Chicago Favorites Ultimate Food and Walking Tour

Chicago in a Day: Food, History & Architecture Walking Tour

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Chicago's Chinatown Food and Walking Tour

Chicago Pizza Tour

Haunted Chicago Booze and Boos Ghost Walking Tour

Downtown Chicago Walking Pizza Tour

Chicago Food Tour: Taste the City’s Most Iconic Eats

Chicago-Style Holiday Hike: Festive Food and Walking Tour

Outdoor Escape Room in Chicago - Fulton Market

Chicago: Chinatown Food & Culture Walking Tour

Chicago: Food and Prohibition Architecture Guided Tour

Fortune Reading with Cheese in Chicago

Private Chicago Foodie Tour

Chicago Scavenger Hunt Adventure