Best results for Tours And Adventures in Chicago, IL

Private Chicago river and lake charter with an included open bar

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

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

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

Private skyline cruise with a local perspective

Trace Chicago's skyscraper story with a donut tasting

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

Ride in a 2-seat supercar and capture your Chicago photo moment

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

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

Trace Chicago's skyline story through Loop landmarks

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

Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

Cruise the Chicago River aboard a private floating tiki bar

Float through Chicago’s skyline on a festive fall hayride

Trace Chicago's haunted lore, gangster history, and true-crime disasters on foot

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Design your own Chicago lakefront day aboard Soulshine

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

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