Name: Congress Plaza Hotel
Price range: CA $204

Top Historic Route 66 Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Hilton Chicago O'Hare Airport

O'Hare

CA $680

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

8.2/10 Very Good! (2,121 reviews)

This hotel is everything anyone would ever need. While I was not fond of the price, it was a great choice and I also booked last minute, so the price is fair.

Reviewed on Sep. 5, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $877

per person

Nov 7 - Nov 11

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (286 reviews)

The staff were excellent

Reviewed on Aug. 21, 2025

Hilton Orrington / Evanston

Downtown Evanston

CA $1,118

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip flight included

Québec (YQB) to Chicago (ORD)

7.6/10 Good! (1,003 reviews)

Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on Aug. 18, 2025

The Langham, Chicago

Downtown Chicago

CA $1,251

per person

Nov 14 - Nov 17

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

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $847

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (1,714 reviews)

Professional service

Reviewed on Sep. 4, 2025

Ready to book your vacation to Historic Route 66?

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Historic Route 66 Hotel Deals

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $179

CA $210 total

Sep 21 - Sep 22

includes taxes & fees

Central Loop Hotel

111 West Adams Street, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $181

CA $213 total

Sep 21 - Sep 22

includes taxes & fees

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $204

CA $240 total

Sep 22 - Sep 23

includes taxes & fees

See all 19,174 properties in Historic Route 66

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.