Historic Route 66 Holidays from AU$963
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The Latest Historic Route 66 Holiday Deals
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was AU$1,181, price is now AU$963 per person
AU$963
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on 7 Oct 2025
Pendry Chicago
Downtown Chicago
Price was AU$1,361, price is now AU$1,027 per person
AU$1,027
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on 11 Oct 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was AU$1,295, price is now AU$977 per person
AU$977
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on 4 Oct 2025
Swissotel - Chicago
Downtown Chicago
Price was AU$1,263, price is now AU$971 per person
AU$971
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice
Reviewed on 9 Oct 2025
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was AU$1,290, price is now AU$1,062 per person
AU$1,062
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Fabulous suite overlooking Millenium Park and Lake Michigan. Clean, attentive staff, and good amenities. Walk to everything.
Reviewed on 10 Oct 2025
Historic Route 66 Holiday
Historic Route 66 Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Arcadia Lake and Flagstaff Convention and Visitors Bureau |
Our pick of the best Historic Route 66 Hotel Deals
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundable
The price is AU$334 per night from 23 Oct to 24 Oct
AU$334
23 Oct - 24 Oct
includes taxes & fees
8.6/10 Excellent! (3,338 reviews)
"Perfecto .Se encuentra en el centro."
Reviewed on 7 Oct 2025
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$334 per night from 23 Oct to 24 Oct
AU$334
23 Oct - 24 Oct
includes taxes & fees
8.4/10 Very Good! (1,869 reviews)
"Room was outdated, bed is very small"
Reviewed on 7 Oct 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$305 per night from 26 Oct to 27 Oct
AU$305
26 Oct - 27 Oct
includes taxes & fees
8/10 Very Good! (9,333 reviews)
"Very clean"
Reviewed on 7 Oct 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.
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Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
