Historic Route 66 Vacation Packages
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Top Historic Route 66 Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,197, price is now CA $1,334 per person
CA $1,334
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $2,153, price is now CA $1,389 per person
CA $1,389
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
It was great for a short stay with my family. We enjoyed the location and proximity to public transportation.
Reviewed on Sep. 4, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,322, price is now CA $1,512 per person
CA $1,512
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Historic Route 66 Hotel Deals
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 14 to Sep 15
CA $185
CA $217 total
Sep 14 - Sep 15
includes taxes & fees
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 14 to Sep 15
CA $185
CA $217 total
Sep 14 - Sep 15
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Sep 22 to Sep 23
CA $204
CA $240 total
Sep 22 - Sep 23
includes taxes & fees
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
