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.
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥262,870
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
The staff was super friendly and the rooms were fantastic, probably the best best I have slept in at a hotel in a while. My friend and I came for the BTS concert and everything we needed and wanted to do was easily accessible by the redline and the CTA
Reviewed on Aug 29, 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.
The Peninsula Chicago
Downtown Chicago
￥1,131,944
per person
Nov 6 - Nov 9
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 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.
Swissotel - Chicago
Downtown Chicago
￥960,459
per person
Nov 6 - Nov 9
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
My sister and I came to Chicago from Baltimore to see the Obama Presidential Center. When I researched hotels to stay at in Chicago I was very impressed with Swissotel ratings. I could’ve made a better choice. We didn’t get to see everything we wanted to see, but when we do come back to Chicago Swissotel is definitely where we’ll be staying. So if you’re planning on coming to Chicago Swissotel is the best choice.
Reviewed on Aug 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥961,530
per person
Nov 6 - Nov 9
found 12 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Great Hotel. A block off the Mile and right in the middle of either direction. Clean rooms, Outstanding breakfast buffet and the bar on the 27th floor with the glass floor platform is really cool and fun. It's our 2nd time staying at this hotel and we'll definitely be back.
Reviewed on Aug 29, 2026
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
￥292,324
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Great Hotel. A block off the Mile and right in the middle of either direction. Clean rooms, Outstanding breakfast buffet and the bar on the 27th floor with the glass floor platform is really cool and fun. It's our 2nd time staying at this hotel and we'll definitely be back.
Reviewed on Aug 29, 2026
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See all available trips from Osaka to Far Southwest Side
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
