Historic Route 66 Ski Vacations

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Top Ski vacation packages in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
￥58,476
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Great extras Good location

Reviewed on Oct 16, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
￥137,816
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Clean space to relax and enjoy your trip

Reviewed on Oct 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥70,021
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
It was an overnight stay for my birthday. The hotel was clean and the staff was friendly.

Reviewed on Oct 16, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥66,276
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Everyone was so nice and accommodating. The location is great. We had a great view of the river.

Reviewed on Oct 15, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
￥77,137
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
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5* Ski vacations in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
￥137,816
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Clean space to relax and enjoy your trip

Reviewed on Oct 15, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
￥1,187,072
per person
Nov 16 - Nov 22
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
￥1,221,889
per person
Nov 16 - Nov 22
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
Don't see what you're looking for?
See all available trips from Louisville to Historic Route 66
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3 Night Ski vacations in Historic Route 66

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

Swissotel - Chicago

Downtown Chicago
￥66,276
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Everyone was so nice and accommodating. The location is great. We had a great view of the river.

Reviewed on Oct 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
￥137,816
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Clean space to relax and enjoy your trip

Reviewed on Oct 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥70,021
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
It was an overnight stay for my birthday. The hotel was clean and the staff was friendly.

Reviewed on Oct 16, 2026

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.