Historic Route 66 Vacations from $392
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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
Price was $761, price is now $392 per person
$392
per person
Jun 24 - Jun 27
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,624 reviews)
The hotel was very charming and clean, room was comfortable. I have some back problems so I was worried when I saw other reviews complaining about the beds but I personally had no issues, they were very comfortable. Lots of parking, and lots of good restaurants within walking distance.
Reviewed on Apr 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,408, price is now $760 per person
$760
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Great room, clean and free breakfast. Close shopping and attractions
Reviewed on Apr 17, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,209, price is now $680 per person
$680
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Very nice and great location. Everyone was very nice. I would definitely stay there again!
Reviewed on Apr 17, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $955, price is now $571 per person
$571
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Room was slightly small and there was no microwave. But for the most part enjoyed my stay.
Reviewed on Apr 15, 2026
Harwelden Mansion
Maple Ridge
Save 100% on your flight
Price was $1,596, price is now $957 per person
$957
per person
Jun 25 - Jun 28
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tulsa (TUL)
10/10 Exceptional! (34 reviews)
Staff was great, rooms were very clean.
Reviewed on Mar 26, 2026
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View all tripsHistoric Route 66 Hotel Deals
Central Loop Hotel
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Apr 19 to Apr 20
$136 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (2,076 reviews)
Good rates, nice room.
Reviewed on Apr 16, 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! (10,127 reviews)
Didn't use bar or car park.
Reviewed on Apr 17, 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! (4,137 reviews)
Great location. Clean room. Friendly staff. Pool was kinda chilly. But that’s the only little criticism
Reviewed on Apr 16, 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.
