Historic Route 66 Luxury Vacations
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Top Luxury vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,055 reviews)
Convenient location in the airport, quick blue line train access. Nice bar and restaurant, friendly and helpful staff.
Reviewed on Jul 27, 2025
Level Chicago Fulton Market
Downtown Chicago
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (229 reviews)
The reason I did not give a five star review is that I was led to believe by Expedia that I was booking a five star hotel. This is basically a very nice apartment building that is 80 percent residential and 20 percent hotel. Not the cool Chicago hotel experience I was expecting. Very nice staff and very clean efficiency apartment.
Reviewed on Jul 21, 2025
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!
Reviewed on Jul 26, 2025
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View all trips5* Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Oct 12 - Oct 18
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
First night we went to bed about 11 pm. When we got in bed it was really scratchy. Discovered a bloody mattress pad on top of the sheet below the comforter, see picture attached. The next day, we
Reviewed on Jul 26, 2025
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!
Reviewed on Jul 26, 2025
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See all available trips from Toronto to Historic Route 66
View all trips3 Night Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
per person
Sep 3 - Sep 6
found 4 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
8.2/10 Very Good! (2,055 reviews)
Convenient location in the airport, quick blue line train access. Nice bar and restaurant, friendly and helpful staff.
Reviewed on Jul 27, 2025
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View all trips4 Night Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Oct 13 - Oct 17
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
First night we went to bed about 11 pm. When we got in bed it was really scratchy. Discovered a bloody mattress pad on top of the sheet below the comforter, see picture attached. The next day, we
Reviewed on Jul 26, 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.