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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥619,115, price is now ￥437,907 per person
￥437,907
per person
May 28 - Jun 2
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Rooms are nice, great view, valet parking is great
Reviewed on Mar 24, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥495,778, price is now ￥352,488 per person
￥352,488
per person
May 28 - Jun 2
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Hilton Chicago
Downtown Chicago
Price was ￥658,325, price is now ￥510,528 per person
￥510,528
per person
May 28 - Jun 2
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
We loved our stay. Two adults and our eight-year-old son took a weekend trip to Chicago. This hotel was very close to the field museum and walking distance to magnificent mile. Short Uber ride to nearby shopping and Willis Tower.
The staff were awesome and upgraded our room at a low price. We felt very safe and staff were very helpful. The eighth floor had a beautiful pool, spa and sauna, great view of lake mi, open late too. We dined for breakfast at yoke and Niu B for dinner. Delicious. At checkout we purchased a future Hilton grand vacation at a great discount too. Let’s go. :)
Reviewed on Mar 25, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥431,334, price is now ￥349,424 per person
￥349,424
per person
May 11 - May 17
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 2026
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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 ￥487,896, price is now ￥398,236 per person
￥398,236
per person
Jun 8 - Jun 12
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit.
We will be back in near future for surr!
Reviewed on Mar 24, 2026
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View all trips3 Night Ski vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥327,888, price is now ￥281,940 per person
￥281,940
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥348,944, price is now ￥302,477 per person
￥302,477
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean!
Reviewed on Mar 25, 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 Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥375,833, price is now ￥299,576 per person
￥299,576
per person
Jun 6 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥395,207, price is now ￥319,152 per person
￥319,152
per person
Jun 6 - Jun 10
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean!
Reviewed on Mar 25, 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.
