things to do in Chicago, IL

Look beyond Uptown's 1920s heyday through the stories behind its buildings

Take the controls in a 30-minute helicopter intro flight

See Chicago from 103 floors up and step out onto glass above the city

Taste Chicago donuts while uncovering Fulton Market’s industrial past

Ride Chicago’s 1920s–30s gangster trail with actor guides

Explore Chicago's Prohibition era through stories of class, nightlife, and rebellion

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Learn About Winemaking in the Heart of Chicago

Trade airport waiting time for a guided taste of Chicago

Taste Chicago classics while exploring the city's landmark-filled streets

Create your own neon canvas with street art techniques and colors that glow under black light

Discover Chicago's riverfront, landmark parks, and Museum Campus in one ride

Explore Chicago Chinatown on a 2026 USA Today 10Best History Tour winner

See Chicago's northwest suburbs and the Fox River from the air

Celebrate with inflatable play and party cleanup handled for you

Taste Santa Monica’s donut culture on an outdoor walking tour

Find your next game across three console libraries

Taste global flavors beyond Chicago's usual food classics

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Tour and tasting for two with a tasting room reservation and wine

Go beyond Chicago’s main sights with a private guide and time in local neighborhoods

Bike Miami Beach and sample local food with a guide

Take the wheel of an open-air supercar with British engineering

Keep your Chicago plans moving with a ride to your chosen downtown stop