Chicago Tours and Trips 2024/2025

We offer 12 tours in Chicago. Tour durations range from 7 to 19 days and the top tour categories in Chicago are explorer, city sightseeing & active and outdoor. Out of the 12 trips in Chicago, 1 of them are private tours and 11 are group tours. Our Chicago tours are offered by 4 qualified and hand-picked tour operators and each Chicago trip comes with a best price guarantee and no added booking fees.

12 Trips in Chicago

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North East Highlights

  • Best price guaranteed
  • No booking fees
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 View Tour
Next Departures
  • Oct 14 Only 10 seats left
  • Dec 23 Only 10 seats left
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New York, Toronto And Chicago Tour

  • Trip customizable
  • Best price guaranteed
7 day city sightseeing tour to New York, Niagara Falls and 2 other destinations in USA, canada and Canada. Read More
  • Tour Type Independent Tour
  • Activities City sightseeing
  • Accommodation Hotel
  • Transport Bus & Flight
  • Age Range 18-99 yrs
  • Operated in English
days07 From US$ 2,162 View Tour
Next Departures
  • May 28 Only 10 seats left
  • May 29 Only 10 seats left
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Essential East Coast, Niagara and Chicago

  • Best price guaranteed
  • No booking fees
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 View Tour
Next Departures
  • Apr 28 10+ seats left
  • May 05 10+ seats left
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Chicago and Niagara Rotary

  • Best price guaranteed
  • No booking fees
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
Add to your Tour Wish List 40% OFFTODAY

Chicago to Golden Gate

  • Best price guaranteed
  • No booking fees
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$ 5,585 US$ 3,351
SavingUS$ 2,234
You've unlocked exclusive savings:
  • Brochure Price:US$ 5,585
  • Special Deal (40%):- US$ 2,234
  • Total Price from:US$ 3,351
View Tour
Next Departures
  • Jun 19 10+ seats left
  • Jul 10 10+ seats left
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Usa and Canada Panorama with Chicago

  • Best price guaranteed
  • No booking fees
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
  • Apr 23 10+ seats left
  • May 07 10+ seats left
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Chicago, Niagara and New York end Washington

  • Best price guaranteed
  • No booking fees
10 day explorer trip 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
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Chicago, Niagara and New York

  • Best price guaranteed
  • No booking fees
8 day explorer tour 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
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Eastern Round ends Chicago

  • Best price guaranteed
  • No booking fees
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
  • Apr 26 10+ seats left
  • May 10 10+ seats left
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Toronto, Niagara and Chicago

  • Best price guaranteed
  • No booking fees
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 05 10+ seats left
  • May 12 10+ seats left
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Unmissable Canada, Niagara and Chicago

  • Best price guaranteed
  • No booking fees
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 01 10+ seats left
  • May 08 10+ seats left
Add to your Tour Wish List 40% OFFTODAY

Chicago to LA

  • Best price guaranteed
  • No booking fees
11 day explorer trip 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$ 5,175 US$ 3,105
SavingUS$ 2,070
You've unlocked exclusive savings:
  • Brochure Price:US$ 5,175
  • Special Deal (40%):- US$ 2,070
  • Total Price from:US$ 3,105
View Tour
Next Departures
  • Jun 19 10+ seats left
  • Jul 10 10+ seats left
Showing 1 - 12 of 12 results
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