Far Southeast Side Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Ski vacation packages in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥374,326
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
What I enjoyed about the property it's very close to the shopping. We enjoyed every moment of staying at Trump Chicago!
Reviewed on Aug 21, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥314,652
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very nice hotel ! Situation perfect! Clean, room are spacious, bed is comfortable, staff very nice.
Reviewed on Aug 21, 2026
Level Chicago Fulton Market
Downtown Chicago
￥314,960
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Excellent front desk staff. Great place, very clean with a touch of everyday luxury. Highly recommend!
Reviewed on Aug 21, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips5* Ski vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥374,326
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
What I enjoyed about the property it's very close to the shopping. We enjoyed every moment of staying at Trump Chicago!
Reviewed on Aug 21, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips3 Night Ski vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥299,384
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very nice hotel ! Situation perfect! Clean, room are spacious, bed is comfortable, staff very nice.
Reviewed on Aug 21, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips4 Night Ski vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
￥314,960
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Excellent front desk staff. Great place, very clean with a touch of everyday luxury. Highly recommend!
Reviewed on Aug 21, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
￥374,326
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
What I enjoyed about the property it's very close to the shopping. We enjoyed every moment of staying at Trump Chicago!
Reviewed on Aug 21, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥369,916
per person
Sep 21 - Sep 25
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very nice hotel ! Situation perfect! Clean, room are spacious, bed is comfortable, staff very nice.
Reviewed on Aug 21, 2026
Don't see what you're looking for?
See all available trips from Sapporo to Far Southeast 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.
