
Historic Route 66 Vacations from $255
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.

The Wildwood Hotel
Price was $529, price is now $255 per person
$255
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,591 reviews)
The whole place was spotless, the staff both professional and friendly, it was an excellent choice for never having been there.
Reviewed on Oct 29, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,159, price is now $512 per person
$512
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Our stay was absolutely excellent! The room was spotless and stylish, but what really stood out was the rooftop — breathtaking views, great ambiance, and the perfect spot to unwind. The concierge team was phenomenal — attentive, knowledgeable, and made every recommendation feel personalized. From check-in to check-out, everything felt seamless and top-tier. Truly a 5-star experience worth repeating!
Reviewed on Oct 28, 2025


Level Chicago – Old Town
Downtown Chicago
Price was $937, price is now $461 per person
$461
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom.
The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine.
Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters.
Reviewed on Oct 29, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $809, price is now $398 per person
$398
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
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Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundable
$116 nightly
The price is $136 total per night from Nov 23 to Nov 24
$136 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (3,391 reviews)
It was a pleasant stay
Reviewed on Oct 28, 2025

Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Nov 23 to Nov 24
$136 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,882 reviews)
Clean
Reviewed on Oct 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Nov 16 to Nov 17
$149 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (5,168 reviews)
The best hotel and best location best breakfast
Reviewed on Oct 29, 2025
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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