
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.

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,719, price is now CA $1,181 per person
CA $1,181
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026

Swissotel - Chicago
Downtown Chicago
Price was CA $2,882, price is now CA $1,972 per person
CA $1,972
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,723, price is now CA $1,886 per person
CA $1,886
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking
Reviewed on May 3, 2026

The Inn at Vanessie
Downtown Santa Fe
Price was CA $2,807, price is now CA $1,952 per person
CA $1,952
per person
Jul 9 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albuquerque (ABQ)
8.8/10 Excellent! (1,002 reviews)
Great location - walkable to all best restaurants and downtown. Had some issues with housekeeping (had to ask for some items) but overall no issues. Great breakfast daily! The “snacks” advertised as “available all day” consisted of granola bars available only 2 of the 5 days we stayed. The bar was closed - apparently due to a recent break-in.
Reviewed on Apr 21, 2026

The Langham, Chicago
Downtown Chicago
Price was CA $2,147, price is now CA $1,518 per person
CA $1,518
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
This was THE BEST hotel we had ever stayed in.
Reviewed on May 4, 2026
Historic Route 66 Hotel Deals

Central Loop Hotel
111 West Adams Street Chicago IL
The price is CA $166 per night from May 25 to May 26
CA $166
CA $198 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (2,116 reviews)
Everything was great
Reviewed on May 6, 2026

The Aquarius Casino Resort, BW Premier Collection
1900 S Casino Dr Laughlin NV
Fully refundableReserve now, pay when you stay
The price is CA $53 per night from May 10 to May 11
CA $53
CA $95 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (7,538 reviews)
👏
Reviewed on May 6, 2026

Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
The price is CA $118 per night from May 25 to May 26
CA $118
CA $182 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,684 reviews)
Friendly staff. Good location
Reviewed on May 5, 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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