Cultural Tours in Chicago, IL

See Art Institute Masterpieces With an Art Historian

Walk Chicago’s must-see sights, including Millennium Park, in 2 hours

Trace Chicago's skyscraper story with a donut tasting

Trace Chicago’s Prohibition history across four neighborhood speakeasies

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

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

See Chicago’s public art and landmark architecture with an expert guide

Explore Chicago through social adventures with fellow solo travelers

Cruise Chicago’s lakefront in an exotic vehicle with skyline and landmark views

Step inside Chicago Loop landmarks and trace the evolution of its skyline

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

Explore Art Institute masterpieces with a private art historian

Walk Chicago’s Pedway and spot hidden details in the Loop

Private skyline cruise with a local perspective

Walk the Loop to see Chicago’s hidden interior architecture

See major works with an art historian guide in a small group

Step inside Chicago’s Art Deco buildings on a 2-hour Loop walk

Explore Chicago's past with a private guide and museum admission included

Trace Chicago's skyline story through Loop landmarks

Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide

Discover Chicago architecture and fireboat history on a guided river cruise.

Walk Logan Square murals and learn the artists behind them