
Historic Route 66 Vacations from $407
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.

Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $637, price is now $407 per person
$407
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,217 reviews)
Had a steak and ribs at the restaurant downstairs and both were delicious
Reviewed on Mar 1, 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


The Wade
Downtown Chicago
Save 100% on your flight
Price was $950, price is now $542 per person
$542
per person
May 10 - May 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,705 reviews)
My stay at The Wade overall was pretty good. I booked here because it has a pool, and I thought I would have a nice view (city view). The view wasn’t available, I was on the 27th floor and only had a view of the roof of other buildings, and other apartments. I kept the window covered for the most part. The pool was unkept in my opinion, I didn’t feel comfortable with the dirt ring on the white tile that surrounded the pool, and the water looked and felt pretty grimy, I felt it needed to be serviced. Though my main attractions to this location were not fulfilled it was very quiet on my floor, the cleaning crew were very polite and generous, and the valet was very friendly and always gave me great service despite it being very busy over the course of my stay.
Reviewed on Mar 2, 2026

Pendry Chicago
Downtown Chicago
Price was $1,060, price is now $678 per person
$678
per person
May 18 - May 21
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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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! (9,918 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! (3,465 reviews)
Every clean, quiet. Perfect location
Reviewed on Mar 6, 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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