Best results for Cultural Tours in Chicago, IL

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

Walk the Loop to see Chicago’s hidden interior architecture

Trace Chicago’s Prohibition history across four neighborhood speakeasies

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

See Art Institute Masterpieces With an Art Historian

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

Explore Art Institute masterpieces with a private art historian

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

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

Walk Wynwood’s street art scene with Wynwood Walls entry included

Walk South Beach and sample local favorites with a guide

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

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

Trace Chicago's skyscraper story with a donut tasting

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

Private skyline cruise with a local perspective

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

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

Explore Chicago through social adventures with fellow solo travelers

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