
Historic Route 66 Vacations from $576
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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 $950, price is now $576 per person
$576
per person
Jun 5 - Jun 8
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

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,294, price is now $686 per person
$686
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with a fantastic shower and amazing shampoo, conditioner and lotion! I’ve even looked into buying it for my home. The breakfast buffet was unbelievable! The food was plentiful with more options than I thought possible. Even more impressive was the breakfast staff who kept the tables clean and the food available, hot and fresh. The hosts took a special interest in knowing the guests, and I know this first hand. My birthday fell during our stay, and the breakfast staff had a table waiting for my family and presented a birthday brownie with the words “Happy Birthday” written in chocolate sauce! Unfortunately, I had unexpectedly been hospitalized for emergency surgery so I missed the opportunity to experience their grand gesture, but the first morning I walked into breakfast after being discharged from the hospital, the host having never see me, asked if my family had given me the brownie. l was blown away! Will I stay again? Without any hesitation!!! Excellent choice!!
Reviewed on Mar 22, 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 21 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

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,178, price is now $735 per person
$735
per person
Jun 5 - Jun 8
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

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
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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! (9,982 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! (3,590 reviews)
The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with ...
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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