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Tours from Chicago

Choose from 8 tours starting in Chicago, and travelling to Dearborn, Las Vegas, Los Angeles, New Orleans, New York and more. May and September are the most popular months to tour from Chicago and we have over 55 departures available from five leading tour operators.

  8 Tours Found
10 Day Dixieland & Rhythms with Cosmos
Tour  
 (19 Reviews)

10 Days Chicago to New Orleans
Operated By: Cosmos (Guided Tour)
“This being our very first tour, it was very good. Our Tour Director (Melanie Wagner) was very good. The coach driver (Jonathan)...”
Exclusive: Earlybird Offer
Departures: Oct 2020 to Nov 2021 (13 Departures)
Countries Visited: USA
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$ 208
From
$ 2,441
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16 Day Highlights of Route 66 with Mother Road Festival & Albuquerque Balloon Fiesta with Cosmos
Tour  
 (1 Reviews)

16 Days Chicago to Los Angeles
Operated By: Cosmos (Guided Tour)
“This is the best trip we have ever done. We went to all the little places still on the route for stops and meals, pace was...”
Exclusive: Earlybird Offer
Departs: 23 September 2021
Countries Visited: USA
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$ 324
From
$ 3,805
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14 Day The Sumptuous Soul of America with Luxury Gold
Tour  
 (2 Reviews)

14 Days Chicago to New Orleans
Operated By: Luxury Gold (Guided Tour)
“We returned from this tour last month, (June 2015 ) our first Insight tour and would highly recommend it. Everything was...”
Exclusive: Mutiple Deals Available
Departures: Apr 2021 to Oct 2021 (6 Departures)
Countries Visited: USA
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$ 1,595
From
$ 7,944
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12 Day Northern Adventure with Contiki
Tour  

12 Days Chicago to Las Vegas or Los Angeles
Operated By: Contiki (Guided Tour)
Journey to USA on this 12 day guided tour with Contiki, beginning your journey in Chicago and travelling through to Las Vegas or Los Angeles.
Departs: 23 September 2020
Countries Visited: USA
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$ 98
From
$ 3,167
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8 Day Mackinac Island with Collette
Tour  

8 Days Chicago to Dearborn or Chicago to Southfield
Operated By: Collette (Guided Tour)
Journey to USA on this 8 day guided tour with Collette, beginning your journey in Chicago and travelling through to Dearborn.
Departures: Jul 2020 to Oct 2021 (18 Departures)
Countries Visited: USA
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$ 196
From
$ 3,647
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8 Day Mackinac Island (Tulip Time Festival) with Collette
Tour  

8 Days Chicago to Southfield
Operated By: Collette (Guided Tour)
Journey to USA on this 8 day guided tour with Collette, beginning your journey in Chicago and travelling through to Southfield.
Departures: May 2021 to May 2021 (3 Departures)
Countries Visited: USA
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$ 172
From
$ 4,127
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11 Day US & Canada Discovery with Intrepid
Tour  

11 Days Chicago to New York
Operated By: Intrepid (Small Group Adventure)
Discover Canada & USA on this 11 day small group adventure with Intrepid, beginning your journey in Chicago and travelling through to New York.
Departures: May 2021 to Sep 2021 (4 Departures)
Countries Visited: Canada, USA
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$ 213
From
$ 5,107
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16 Day Highlights of Route 66 with Cosmos
Tour  
 (17 Reviews)

16 Days Chicago to Los Angeles
Operated By: Cosmos (Guided Tour)
“This was a bucket list tour and we were very pleased to have completed it. The tour was good, the tour director was great...”
Exclusive: Earlybird Offer
Departures: May 2021 to Sep 2021 (9 Departures)
Countries Visited: USA
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$ 286
From
$ 3,353
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