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.
Baymont by Wyndham Glenview
Price was CA $768, price is now CA $557 per person
CA $557
per person
Jul 30 - Aug 2
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,004 reviews)
Breakfast was there but not a lot
Look at moving in individuals using it as a home
Good location though nice area around the place
Reviewed on May 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,355, price is now CA $1,579 per person
CA $1,579
per person
Jul 30 - Aug 2
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,605, price is now CA $1,100 per person
CA $1,100
per person
Jun 28 - Jul 3
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (105 reviews)
Such a cute hotel , reminded me of some I’ve stayed in in Europe !! And the location was perfect
Reviewed on May 4, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,235, price is now CA $899 per person
CA $899
per person
Aug 1 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Historic Route 66 Hotel Deals
Central Loop Hotel
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (2,131 reviews)
Good experience at All. Thanks
Reviewed on May 10, 2026
Avi Resort & Casino
10000 Aha Macav Pkwy Laughlin NV
The price is CA $77 per night from May 12 to May 13
CA $77
CA $87 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (4,681 reviews)
La habitación súper sucia
Reviewed on May 10, 2026
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from May 25 to May 26
CA $119
CA $183 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,699 reviews)
Small room but perfect for one person. Lovely modern bathroom. Good fitness room. Super friendly and helpful front desk staff
Reviewed on May 10, 2026
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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