Guided Route 66 Car Caravan
a 13-day Mother Road adventure from Chicago to LA
2026 Pricing Only $40
Loading days...
3 hr
40 US dollars
Explore the heart of Chicago and Route 66 on our 3 hour walking tour
Be immersed in the sights and sweets of downtown Chicago, the architecture of America's 3rd largest city, and the history of the Mother Road.
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Each tour begins at the start of Route 66, right in front of the famed Art Institute of Chicago. From there, we'll explore both streets that comprise Route 66 in downtown Chicago and end just off Route 66 at the beautiful Harold Washington Library.
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If you're looking to learn about Route 66, but also learn about Chicago history and architecture, this is the perfect tour for you.
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Oh, and one more bonus... Each tour features 3 authentic Chicago culinary treats!
Contact us for group discounts and private tours!
What's included:
3 Iconic Chicago Sweets
Tote Bag with RT66 stickers
Expert Tour Guide




Itinerary Basics:
Tour Start: Art Institute
Tour End: Harold Washington Library
Tour Length: 2 miles (with breaks)
Tour Duration: Approx. 2.5-3 hours
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Featured Tour Highlights:
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"Route 66 Begins" Sign
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Palmer House Hilton
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Berghoff Restaurant
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The Rookery
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Chicago River
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Old St. Pats
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Lou Mitchell's
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Union Station
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Willis Tower
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Board of Trade
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Harold Washington Library
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...and more!

