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 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,627 reviews)
Poor quality breakfast buffet, unsecured parking, worn furnishings, in need of a redo. Overpriced for conditions.
Reviewed on Apr 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,186, price is now $691 per person
$691
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,831 reviews)
Great room, clean and free breakfast. Close shopping and attractions
Reviewed on Apr 17, 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 19 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
Le Méridien Essex Chicago
Downtown Chicago
Save 100% on your flight
Price was $822, price is now $500 per person
$500
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $857, price is now $522 per person
$522
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
It’s a bit loud on the weekend. There is no daily housekeeping but great space and great location.
Reviewed on Apr 17, 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! (2,077 reviews)
Good rates, nice room.
Reviewed on Apr 16, 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! (4,138 reviews)
Great location. Clean room. Friendly staff. Pool was kinda chilly. But that’s the only little criticism
Reviewed on Apr 16, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (5,855 reviews)
Clean and easy check in.
Reviewed on Apr 17, 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.
