Historic Route 66 Vacations from $339
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
Save 100% on your flight
Price was $615, price is now $339 per person
$339
per person
Jun 21 - Jun 25
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,627 reviews)
The breakfaat was average, thou fresh. There was enough street parking nearby, safe.
Reviewed on Mar 30, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $502 per person
$502
per person
Jun 12 - Jun 15
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,551, price is now $953 per person
$953
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.
Reviewed on Apr 11, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,157, price is now $725 per person
$725
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
The room is really a small apartment. Fulton Market area is quite energetic. Quite nice.
Reviewed on Apr 12, 2026
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Central Loop Hotel
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Apr 13 to Apr 14
$129 total
Apr 13 - Apr 14
Total with taxes and fees
8.6/10 Excellent! (2,063 reviews)
Super nice people.
Reviewed on Apr 10, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $161 total per night from Apr 26 to Apr 27
$161 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,106 reviews)
Steve, the doorman, was excellent and helpful. The hotel has a charming, old world elegance with a friendly vibe. Great location. Would come back.
Reviewed on Apr 12, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (4,113 reviews)
Everything was great
Reviewed on Apr 12, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Historic Route 66 Vacation Packages
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.
