Historic Route 66 Vacations from $331
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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
Price was $677, price is now $331 per person
$331
per person
May 11 - May 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Just a block off of Michigan Avenue made this hotel a great location for shops food and people watching! Great selection of breakfast buffet. Stayed 2nd time staying at this hotel. Will continue to stay here when we’re in Chicago. No valet parking though but parking garage is just around the corner street.
Reviewed on Mar 5, 2026
La Banque Hotel
Price was $759, price is now $419 per person
$419
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (467 reviews)
Room was amazing and beautiful and comfortable
Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous
Reviewed on Mar 1, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $818, price is now $470 per person
$470
per person
May 11 - May 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,136 reviews)
Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries.
Reviewed on Mar 1, 2026
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Historic Route 66 Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $118 total per night from Mar 30 to Mar 31
$118 total
Mar 30 - Mar 31
Total with taxes and fees
8/10 Very Good! (9,917 reviews)
Fantastic Location! Friendly staff, lots of history. Central Heating during the winter, so you’ll have to open a window to avoid getting toasted. Overall great bang for your buck and right next to several transportation options!
Reviewed on Mar 5, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Mar 24 to Mar 25
$169 total
Mar 24 - Mar 25
Total with taxes and fees
9.4/10 Exceptional! (3,461 reviews)
Just a block off of Michigan Avenue made this hotel a great location for shops food and people watching! Great selection of breakfast buffet. Stayed 2nd time staying at this hotel. Will continue to stay here when we’re in Chicago. No valet parking though but parking garage is just around the corner ...
Reviewed on Mar 5, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $144 total per night from Mar 23 to Mar 24
$144 total
Mar 23 - Mar 24
Total with taxes and fees
8.6/10 Excellent! (5,716 reviews)
Old property bad food long lines
Reviewed on Mar 5, 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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