Historic Route 66 Vacations from $348

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

Downtown Chicago
Save 100% on your flight
$348
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (2,721 reviews)
The Wildwood Hotel

The Wildwood Hotel

$563
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,672 reviews)
Good covered parking. Won't get wet. Very nice motel for the price. Would stay again.

Reviewed on Aug 6, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
$2,744
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

Save 100% on your flight
$651
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
10/10 Exceptional! (1 review)
The property was excellent, and the home was very warm and welcoming.

Reviewed on Jun 25, 2026

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

Downtown Chicago
Save 100% on your flight
$600
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,933 reviews)
The breakfast was very minimal.

Reviewed on Aug 7, 2026

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Historic Route 66 Essential Information

Language
English
Currency
U.S dollars

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.