Far North Side Ski Vacations
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Top Ski vacation packages in Far North Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥345,638, price is now ￥294,373 per person
￥294,373
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
The room was fantastic, the hotel bar was fantastic, the staff was fantastic. My only complaint is the restaurant closed at 9p on a Saturday. Overall four out of five experience
Reviewed on May 25, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥386,636, price is now ￥315,888 per person
￥315,888
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk.
Reviewed on May 25, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥452,328, price is now ￥375,986 per person
￥375,986
per person
Aug 2 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Great hotel. Loved the lobby and our room. Would definitely stay here again.
Reviewed on May 19, 2026
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was ￥438,648, price is now ￥377,942 per person
￥377,942
per person
Aug 2 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (142 reviews)
My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced.
Reviewed on Sep 5, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥347,334, price is now ￥305,305 per person
￥305,305
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Super location, good crowd of staff and fellow travellers. Smells great!
Reviewed on May 24, 2026
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View all trips5* Ski vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥341,037, price is now ￥333,635 per person
￥333,635
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Our stay was a truly wonderful experience that made our 25th wedding anniversary celebration incredibly special. We are deeply grateful for the Four Seasons staff's thoughtful and attentive hospitality.
Reviewed on May 22, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥699,977, price is now ￥527,073 per person
￥527,073
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Great experience! Would stay here agin
Reviewed on May 18, 2026
The Langham, Chicago
Downtown Chicago
Price was ￥455,810, price is now ￥426,228 per person
￥426,228
per person
Aug 2 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Fantastic hotel and amazing spa! Beautiful room with fantastic staff
Reviewed on May 16, 2026
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View all trips3 Night Ski vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was ￥408,932, price is now ￥351,806 per person
￥351,806
per person
Aug 2 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥449,300, price is now ￥369,966 per person
￥369,966
per person
Aug 2 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Great experience! Would stay here agin
Reviewed on May 18, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥452,328, price is now ￥375,986 per person
￥375,986
per person
Aug 2 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Great hotel. Loved the lobby and our room. Would definitely stay here again.
Reviewed on May 19, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Far North Side
View all trips4 Night Ski vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥376,456, price is now ￥309,615 per person
￥309,615
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
The room was fantastic, the hotel bar was fantastic, the staff was fantastic. My only complaint is the restaurant closed at 9p on a Saturday. Overall four out of five experience
Reviewed on May 25, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥386,636, price is now ￥315,888 per person
￥315,888
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk.
Reviewed on May 25, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥400,240, price is now ￥332,040 per person
￥332,040
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (394 reviews)
The staff was great and everything was nice and clean
Reviewed on May 24, 2026
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See all available trips from Tokyo to Far North 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.
