Historic Route 66 Vacations from $443
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $863, price is now $443 per person
$443
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)
Great stay! Loved to come back. Friendly staff!
Reviewed on Apr 13, 2026
Baymont By Wyndham Schaumburg Chicago Northwest
Save 100% on your flight
Price was $897, price is now $464 per person
$464
per person
May 18 - May 22
found 5 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
No reviews
Everyone was nice, room was what i expected, and the late checkout policy was helpful and clear and easy to approach.
Reviewed on Apr 11, 2026
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,066, price is now $569 per person
$569
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
They need to update the lobby real bad. Location is convenient a short walk to Willis Tower and you can self park very close.
Reviewed on Apr 3, 2026
Level Chicago – Old Town
Downtown Chicago
Price was $1,613, price is now $917 per person
$917
per person
Jun 25 - Jun 30
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 2026
The Wildwood Hotel
Save 100% on your flight
Price was $940, price is now $552 per person
$552
per person
Jul 10 - Jul 12
found 17 hours 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
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View all tripsHistoric Route 66 Hotel Deals
Central Loop Hotel
111 West Adams Street Chicago IL
$116 nightly
The price is $136 total per night from Apr 26 to Apr 27
$136 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (2,072 reviews)
Perfect location and an amazing value. The room was so comfortable and nicely appointed. Friendly and professional staff. I definitely recommend!!
Reviewed on Apr 14, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $161 total per night from Apr 26 to Apr 27
$161 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,140 reviews)
Shower and sink were terrible. Barely hot water but took fine tuning to find where it would be hot and not cold. We had to fiddle with shower for 20 minutes every morning before shower. Also the toilet handle shot water water out when flushing.
Reviewed on Apr 14, 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! (4,128 reviews)
Clean
Reviewed on Apr 13, 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.
