Historic Route 66 Vacations from $390
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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 $678, price is now $390 per person
$390
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $850, price is now $462 per person
$462
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Very beautiful hotel! Room was spacious and clean and great front desk service, especially Francisco he was very nice and even let me check in early..which was greatly appreciated.
Reviewed on Apr 8, 2026
Still Waters Resort
Save 100% on your flight
Price was $1,953, price is now $1,176 per person
$1,176
per person
Jun 10 - Jun 16
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Springfield (SGF)
8.8/10 Excellent! (4,602 reviews)
The property and staff were great. The amenities provide a lot of activities for kids and adults. It has got more expensive over the past 2 years, but we still enjoyed our time. We'll be back!
Reviewed on Apr 7, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,394, price is now $845 per person
$845
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
Very nice and clean hotel
Reviewed on Apr 8, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $1,591, price is now $1,008 per person
$1,008
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Restaurant next door can be loud and surprise you when entering the lobby. Great location. Will return.
Reviewed on Apr 8, 2026
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View all tripsHistoric Route 66 Hotel Deals
Central Loop Hotel
111 West Adams Street Chicago IL
$93 nightly
The price is $109 total per night from Apr 9 to Apr 10
$109 total
Apr 9 - Apr 10
Total with taxes and fees
8.6/10 Excellent! (2,055 reviews)
Not so good but worth the price
Reviewed on Apr 8, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,064 reviews)
Not used
Reviewed on Apr 8, 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! (4,079 reviews)
Great room for the price and location. Convenience store right accross the street if you need anything. Just wish parking was included
Reviewed on Apr 8, 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.
