Historic Route 66 Vacations from $374
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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 $971, price is now $612 per person
$612
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Breakfast was so good!! Very friendly staff !!! Clean !!
Reviewed on Mar 24, 2026
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $856 per person
$856
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Center of everything.. Will book again!!!
Reviewed on Mar 24, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,086, price is now $727 per person
$727
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Rooms are nice, great view, valet parking is great
Reviewed on Mar 24, 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! (10,010 reviews)
After you get past the look of the hotel and embrace the history, you will appreciate staying here. The breakfast food from the only restaurant open was terrible but the food from the bar was better. The front desk employees left something to be desired but the security went above and beyond.
Reviewed on Mar 24, 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! (3,620 reviews)
Breakfast was so good!! Very friendly staff !!! Clean !!
Reviewed on Mar 24, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$130 nightly
The price is $153 total per night from Apr 5 to Apr 6
$153 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (5,762 reviews)
This was our first booked trip as a family of 4 and our stay was excellent. Highlight of the stay was the breakfast. We wanted to get to the pool, but it got shut down early Friday night due to an accident. Hotel is in a great spot for walking around and accessing the majority of downtown Chicago. ...
Reviewed on Mar 24, 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.
