Historic Route 66 Vacations from $402
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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 $629, price is now $402 per person
$402
per person
May 31 - Jun 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,011, price is now $556 per person
$556
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
We loved the breakfast and how convenient the hotel is from the Magnificent Mile and the river walk.
Reviewed on Mar 23, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $692, price is now $445 per person
$445
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Staff were great in dealing with many of our needs
Reviewed on Mar 22, 2026
Pendry Chicago
Downtown Chicago
Price was $1,015, price is now $653 per person
$653
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special!
Reviewed on Mar 16, 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! (9,997 reviews)
renovate room barhroom
Reviewed on Mar 22, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Mar 29 to Mar 30
$190 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (3,600 reviews)
We loved the breakfast and how convenient the hotel is from the Magnificent Mile and the river walk.
Reviewed on Mar 23, 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! (5,773 reviews)
The staff was super helpful and friendly. The room was clean and the bed was super comfortable! Perfect place to walk to lots of things.
Reviewed on Mar 22, 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.
