Historic Route 66 Vacations from $674
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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 $1,151, price is now $674 per person
$674
per person
Apr 29 - May 6
found 6 hours ago
Roundtrip flight included
Boston (BOS) to St. Louis (STL)
9.2/10 Wonderful! (1,620 reviews)
the hotel is very comfortable and the staff was very helpful.
Reviewed on Mar 20, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $780 per person
$780
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.
Reviewed on Mar 14, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $887 per person
$887
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,278, price is now $788 per person
$788
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great location, views, & amenities.
Reviewed on Mar 20, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,600, price is now $1,668 per person
$1,668
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!
Reviewed on Mar 17, 2026
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View all tripsHistoric Route 66 Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Apr 1 to Apr 2
$136 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,976 reviews)
Everything was clean and the staff were very nice!
Reviewed on Mar 20, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $183 total per night from Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,576 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.
Reviewed on Mar 20, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (5,757 reviews)
Hotel is conveniently located, clean and rooms were spacious. Evening reception and breakfast selections are fantastic. The only downside was the pool area is small with limited seating but the kiddos still enjoyed. Staff was very professional and helpful. Would stay again.
Reviewed on Mar 20, 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.
