Walking Tours in Chicago
See the city at street level, at a pace where the stories can breathe. Every one of the 4 tours below is run by our own local team in Chicago. You book direct with the operator, never a marketplace.
4 Tours Available
The Top 4 Walking Tours in Chicago

Chicago, United States
Best of Chicago History & Architecture Walking Tour with Boat Cruise
- 3.5 Hours Duration
- Max 10 Guests Per Group

Chicago, United States
Best of Chicago History & Architecture Walking Tour
- 2.5 Hours Duration
- Max 10 Guests Per Group

Chicago, United States
Chicago Small Group Walking Tour with Skydeck and Boat Cruise
- 4 Hours Duration
- Max 10 Guests Per Group
Find the perfect experience for you
| Tour | ||||
|---|---|---|---|---|
| Price | $104 | $49 | $189 | $159 |
| Duration | 4 Hours | 3 Hours | 4 Hours | 4 Hours |
| Group size | Up to 10 guests | Up to 10 guests | Up to 10 guests | Up to 10 guests |
| Highlights | Explore Millennium Park and see the iconic Cloud Gate (“The Bean”) and Crown Fountain | Explore Millennium Park and see the iconic Cloud Gate (“The Bean”) and Crown Fountain | Ascend to the 103rd floor of Willis Tower for Skydeck Chicago walking tour and take in sweeping views from The Ledge. | — |
| Book | Check Availability | Check Availability | Check Availability | Check Availability |
Book Direct with the Local Team
Rated 4.6/5 across Viator, TripAdvisor, Google & more.
- Best-price guarantee when you book direct
- Change-of-Plans Guarantee: free cancellation up to 24h before
- Direct line to the team that runs your tour
- Instant confirmation