Historic Route 66 Mountain Vacations
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Top Mountain vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
￥93,126
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
I hate not being able to make coffee in my room, hate to get dressed to go down stairs to get coffee
Reviewed on Oct 13, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
￥133,892
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Hotel was conveniently located, near two train stations. All staff we encountered were friendly and courteous.
Reviewed on Oct 12, 2026
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View all trips5* Mountain vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
￥319,507
per person
Nov 16 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Service was superb. However, the mattress was too soft for me. The comforter has a bloody spot on it that should have been replaced.
Reviewed on Oct 12, 2026
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View all trips4 Night Mountain vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
￥133,892
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Hotel was conveniently located, near two train stations. All staff we encountered were friendly and courteous.
Reviewed on Oct 12, 2026
Don't see what you're looking for?
See all available trips from Nashville to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
