Small-Group Tours in Chicago
Our signature format: a small group, a local guide, and room to actually experience each stop. Every one of the 6 tours below is run by our own local team in Chicago. You book direct with the operator, never a marketplace.
4.6/5(50 reviews)|6 Tours Available
The Top 6 Small-Group Tours in Chicago

Chicago, United States
(41)
Best of Chicago Tour
Tickets includedSkip-the-line
- 4 Hours Duration
- Max 10 Guests Per Group

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 | $129 | $104 | $49 | $189 |
| Duration | 4 Hours | 4 Hours | 3 Hours | 4 Hours |
| Group size | Up to 10 guests | Up to 10 guests | Up to 10 guests | Up to 10 guests |
| Highlights | Relax on Shoreline Architecture Cruise and see over 40 iconic Chicago landmarks from the river | 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 |
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