Central Chicago Ski Vacations
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Top Ski vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥134,050, price is now ￥106,621 per person
￥106,621
per person
Jun 12 - Jun 14
found 11 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's
Reviewed on May 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥178,026, price is now ￥127,511 per person
￥127,511
per person
Jun 12 - Jun 14
found 11 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Great location & breakfast was amazing.
Reviewed on May 11, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥142,830, price is now ￥111,552 per person
￥111,552
per person
Jun 12 - Jun 14
found 11 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on May 12, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥137,655, price is now ￥112,510 per person
￥112,510
per person
Jun 12 - Jun 14
found 11 hours ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
9/10 Wonderful! (3,506 reviews)
Everything was great ! It was so clean, the staff was very nice and the hotel is beautiful. The food was good and valet was very fast every time I needed my vehicle.
Reviewed on May 12, 2026
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View all trips5* Ski vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥425,590, price is now ￥399,524 per person
￥399,524
per person
Jul 27 - Jul 30
found 22 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Loved our suite- gorgeous views! Great service and excellent location
Reviewed on May 8, 2026
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View all trips4 Night Ski vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥433,054, price is now ￥359,343 per person
￥359,343
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Great location & breakfast was amazing.
Reviewed on May 11, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
