Historic Route 66 Vacations from $520
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $834, price is now $520 per person
$520
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again.
Reviewed on Mar 19, 2026
The Wildwood Hotel
Save 100% on your flight
Price was $1,120, price is now $690 per person
$690
per person
Apr 21 - Apr 24
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,703, price is now $1,737 per person
$1,737
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!
Reviewed on Mar 17, 2026
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,000, price is now $666 per person
$666
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room
Reviewed on Mar 20, 2026
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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! (9,981 reviews)
It’s an old hotel. It needs a quality paint job and new carpets in the hallways among many other things. But the lake view rooms makes up for a lot of what’s missing.
Reviewed on Mar 22, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $183 total per night from Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,587 reviews)
it was just perfect! thank you
Reviewed on Mar 22, 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! (5,765 reviews)
Spent three nights with husband and teenage son over spring break. Young man who checked us in was not friendly, did not mention happy hour, or breakfast. He did not give us any information except room number. Breakfast staff was nice and polite. Recommend getting to breakfast early or there will ...
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.
