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Tours from Chicago

Choose from 8 tours starting in Chicago, and travelling to Boston, Los Angeles, New Orleans, New York and Southfield. June and September are the most popular months to tour from Chicago and we have over 78 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: Free SafetyNet
Departures: May 2021 to Oct 2022 (21 Departures)
Countries Visited: USA
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$ 120
From
$ 2,572
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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: Free SafetyNet
Departures: May 2021 to Sep 2022 (16 Departures)
Countries Visited: USA
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$ 176
From
$ 3,628
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7 Day North East Highlights with Contiki
Tour  

7 Days Chicago to New York or Boston
Operated By: Contiki (Guided Tour)
Journey to USA on this 7 day guided tour with Contiki, beginning your journey in Chicago and travelling through to New York or Boston.
Exclusive: $99 Deposit Offer
Departures: Apr 2022 to Mar 2023 (20 Departures)
Countries Visited: USA
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$ 74
From
$ 2,397
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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: Free SafetyNet
Departs: 23 September 2021
Countries Visited: USA
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$ 171
From
$ 4,108
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8 Day Mackinac Island 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: Jun 2021 to Oct 2021 (13 Departures)
Countries Visited: USA
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$ 192
From
$ 4,311
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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: Jun 2021 to Oct 2021 (4 Departures)
Countries Visited: USA
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$ 2,598
From
$ 7,698
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14 Day Historic Route 66 with Exodus Travels
Tour  

14 Days Chicago to Los Angeles
Operated By: Exodus Travels (Small Group Adventure)
Journey to USA on this 14 day small group adventure with Exodus Travels, beginning your journey in Chicago and travelling through to Los Angeles.
Departs: 26 June 2021
Countries Visited: USA
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$ 287
From
$ 6,892
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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 (2 Departures)
Countries Visited: USA
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$ 331
From
$ 3,968
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