4.8(114)
Official Chicago Architecture Cruise by First Lady
Tours
From$57
City guides
Chicago Walking Tours
Chicago makes the most sense when you see it at street level, especially in neighbourhoods where landmarks, local stories, and city texture sit close together. These walking-led picks focus on guided routes and sightseeing formats that help travellers cover more ground with context.
Picks
10
Experiences
95
Walking-tour, guided, sightseeing, and street-level discovery signals.
Included for strong walking-tour or guided-sightseeing relevance.
5.0Lake Michigan & Chicago River: 1.5-Hr Night Sightseeing Cruise
Tours
From$50
Included for strong walking-tour or guided-sightseeing relevance.
5.0Chicago Architecture: A Walk Through Time
Theatre
From$30
Included for strong walking-tour or guided-sightseeing relevance.
5.0Chicago Bus Tour: 90-Min Sunset Tour
Tours
From$39
Included for strong walking-tour or guided-sightseeing relevance.
5.0Chicago: Chinatown Food & Culture Walking Tour
Theatre
From$79.99
Included for strong walking-tour or guided-sightseeing relevance.
5.0Chicago: Food and Prohibition Architecture Guided Tour
Tours
From$99
Included for strong walking-tour or guided-sightseeing relevance.
5.0Chicago: Underground Pedway & the Loop Guided Walking Tour
Theatre
From$35
Included for strong walking-tour or guided-sightseeing relevance.
5.0The Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided Tour
Tours
From$84
Included for strong walking-tour or guided-sightseeing relevance.
5.0Tiffany in Chicago: Guided Tour
Theatre
From$30
Included for strong walking-tour or guided-sightseeing relevance.
5.0Chicago: Family & Food Guided Bike Tour
Tours
From$79.99
Included for strong walking-tour or guided-sightseeing relevance.