Western Suburbs Ski Vacations

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Top Ski vacation packages in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥230,642
per person
Nov 9 - Nov 13
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥318,611
per person
Nov 9 - Nov 13
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥254,218
per person
Nov 9 - Nov 13
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,867 reviews)
Hotel was mediocre. The cleanliness of the hotel was 5/10, it didn’t have a pleasant smell and empty food trays in the hallways. The views were nice from the room.

Reviewed on Sep 29, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥256,848
per person
Nov 9 - Nov 13
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago
¥232,054
per person
Nov 9 - Nov 13
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (2,907 reviews)
Excellent location

Reviewed on Sep 29, 2026

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5* Ski vacations in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
¥356,482
per person
Nov 19 - Nov 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (922 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥422,594
per person
Nov 19 - Nov 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥448,845
per person
Nov 19 - Nov 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
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3 Night Ski vacations in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥384,162
per person
Nov 29 - Dec 2
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
¥394,684
per person
Nov 29 - Dec 2
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (3,913 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥392,832
per person
Nov 29 - Dec 2
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (2,401 reviews)
Had a great trip, great location, helpful staff.

Reviewed on Sep 29, 2026

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4 Night Ski vacations in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥230,642
per person
Nov 9 - Nov 13
found 18 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥342,510
per person
Nov 9 - Nov 13
found 1 hour ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on Sep 29, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥318,611
per person
Nov 9 - Nov 13
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
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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.