Chicago Tours and Trips 2024/2025
We offer 11 tours in Chicago. Tour durations range from 7 to 19 days and the top tour categories in Chicago are explorer, active and outdoor & city sightseeing.. Our Chicago tours are offered by 3 qualified and hand-picked tour operators and each Chicago trip comes with a best price guarantee and no added booking fees.
11 Trips in Chicago
- Starts Chicago, USA
- Ends New York, USA
North East Highlights
7 day active and outdoor tour in USA, visiting Chicago, Catskill Mountains and Boston. Read More
- Tour Type Group Tour
- Activities Active and outdoor & City sightseeing
- Accommodation Hotel
- Transport Coach & Flight
- Age Range 18-35 yrs
- Operated in English
days07
From
US$ 2,265
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Next Departures
- Oct 14 10+ seats left
- Dec 23 10+ seats left
- Starts New York, USA
- Ends Chicago, USA
Essential East Coast, Niagara and Chicago
14 day explorer tour visiting New York and Chicago in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat & Train
- Age Range 15-99 yrs
- Operated in English
days14
From
US$ 2,684
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Next Departures
- May 05 10+ seats left
- May 12 10+ seats left
- Starts Chicago, USA
- Ends Chicago, USA
Chicago and Niagara Rotary
8 day explorer tour visiting Chicago in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat & Train
- Age Range 15-99 yrs
- Operated in English
days08
From
US$ 1,534
View Tour
Next Departures
- May 03 10+ seats left
- May 10 10+ seats left
- Starts Chicago, USA
- Ends San Francisco, USA
Chicago to Golden Gate
14 day explorer tour through Chicago, Sioux Falls, Rapid City and 12 other destinations in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel & Lodge
- Transport Bus & Coach
- Age Range 18-39 yrs
- Operated in English
days14
From
US$ 5,902
US$ 3,541
SavingUS$ 2,361
View Tour
You've unlocked exclusive savings:
- Brochure Price:US$ 5,902
- Special Deal (40%):- US$ 2,361
- Total Price from:US$ 3,541
Next Departures
- Jun 19 10+ seats left
- Jul 10 10+ seats left
- Starts Los Angeles, USA
- Ends Chicago, USA
Usa and Canada Panorama with Chicago
19 day explorer tour visiting Los Angeles and Chicago in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat, Flight & Train
- Age Range 15-99 yrs
- Operated in English
days19
From
US$ 3,624
View Tour
Next Departures
- May 07 10+ seats left
- May 14 10+ seats left
- Starts Chicago, USA
- Ends Washington D.C., USA
Chicago, Niagara and New York end Washington
10 day explorer tour visiting Chicago and Washington D.C. in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat & Train
- Age Range 15-99 yrs
- Operated in English
days10
From
US$ 1,917
View Tour
Next Departures
- May 03 10+ seats left
- May 10 10+ seats left
- Starts Chicago, USA
- Ends New York, USA
Chicago, Niagara and New York
8 day explorer trip visiting Chicago and New York in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat & Train
- Age Range 15-99 yrs
- Operated in English
days08
From
US$ 1,534
View Tour
Next Departures
- May 03 10+ seats left
- May 10 10+ seats left
- Starts Washington D.C., USA
- Ends Chicago, USA
Eastern Round ends Chicago
16 day explorer trip visiting Washington D.C. and Chicago in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat & Train
- Age Range 15-99 yrs
- Operated in English
days16
From
US$ 3,067
View Tour
Next Departures
- May 10 10+ seats left
- May 17 10+ seats left
- Starts Toronto, Canada
- Ends Chicago, USA
Toronto, Niagara and Chicago
7 day explorer tour to Toronto and Chicago traveling through Canada and USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat & Train
- Age Range 15-99 yrs
- Operated in English
days07
From
US$ 1,203
View Tour
Next Departures
- May 12 10+ seats left
- May 19 10+ seats left
- Starts Montreal, Canada
- Ends Chicago, USA
Unmissable Canada, Niagara and Chicago
11 day explorer tour to Montreal and Chicago traveling through Canada and USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel
- Transport Bus, Boat & Train
- Age Range 15-99 yrs
- Operated in English
days11
From
US$ 2,109
View Tour
Next Departures
- May 08 10+ seats left
- May 15 10+ seats left
- Starts Chicago, USA
- Ends Los Angeles, USA
Chicago to LA
11 day explorer tour visiting Chicago and Los Angeles in USA. Read More
- Tour Type Group Tour
- Activities Explorer
- Accommodation Hotel & Lodge
- Transport Bus & Coach
- Age Range 18-39 yrs
- Operated in English
days11
From
US$ 5,470
US$ 3,282
SavingUS$ 2,188
View Tour
You've unlocked exclusive savings:
- Brochure Price:US$ 5,470
- Special Deal (40%):- US$ 2,188
- Total Price from:US$ 3,282
Next Departures
- Jun 19 10+ seats left
- Jul 10 10+ seats left
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