Historic Route 66 Vacations from $144
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $313, price is now $144 per person
$144
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early!
There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there.
This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.
Reviewed on Nov 10, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $470, price is now $232 per person
$232
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Rooms are lovely, bar / restaurant is top notch. Love staying at the pendry!
Reviewed on Nov 10, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $634, price is now $329 per person
$329
per person
Jan 22 - Jan 26
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,161, price is now $1,148 per person
$1,148
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Room exceptional well kept, staff extremely nice Ms Diana in the front desk and Luis in the concierge were superb
Reviewed on Nov 10, 2025
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Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $107 total per night from Dec 11 to Dec 12
$107 total
Dec 11 - Dec 12
Total with taxes and fees
8.6/10 Excellent! (3,278 reviews)
Great location at reasonable rates
Reviewed on Nov 4, 2025
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $107 total per night from Dec 11 to Dec 12
$107 total
Dec 11 - Dec 12
Total with taxes and fees
8.4/10 Very Good! (1,884 reviews)
Great
Reviewed on Nov 8, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$100 nightly
The price is $117 total per night from Nov 25 to Nov 26
$117 total
Nov 25 - Nov 26
Total with taxes and fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included
Reviewed on Nov 10, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.