Far Southwest Side Ski Vacations
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Top Ski vacation packages in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥659,915, price is now ￥426,058 per person
￥426,058
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Many restaurants and attractions nearby,Staff pleasant, everything was clean
Reviewed on Mar 12, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥560,889, price is now ￥424,265 per person
￥424,265
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥415,929, price is now ￥356,362 per person
￥356,362
per person
May 29 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Friendly staff, beautiful location, vista rooms and vista suites both lovely, views of river.
Reviewed on Mar 12, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥526,376, price is now ￥478,474 per person
￥478,474
per person
May 29 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026
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See all available trips from Tokyo to Far Southwest Side
View all trips5* Ski vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥405,564, price is now ￥335,298 per person
￥335,298
per person
May 12 - May 15
found 7 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
Room was perfect/staff was great
Reviewed on Mar 12, 2026
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See all available trips from Osaka to Far Southwest Side
View all trips3 Night Ski vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥415,929, price is now ￥356,362 per person
￥356,362
per person
May 29 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Friendly staff, beautiful location, vista rooms and vista suites both lovely, views of river.
Reviewed on Mar 12, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥526,376, price is now ￥478,474 per person
￥478,474
per person
May 29 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips4 Night Ski vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
Price was ￥366,858, price is now ￥338,528 per person
￥338,528
per person
May 28 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.4/10 Good! (2,522 reviews)
The staff were very friendly and attentive. Perfect location to go to and from the busy part of downtown Chicago. It was nice going back to quiet after the bustle :)
Reviewed on Mar 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
Excellent experience
Reviewed on Mar 11, 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was ￥471,826, price is now ￥426,446 per person
￥426,446
per person
May 28 - Jun 1
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,873 reviews)
great area with lots of options nearby, close to the train & bus stop, and very safe!
Reviewed on Mar 8, 2026
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See all available trips from Tokyo to Far Southwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
