Central Illinois Ski Vacations

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Top Ski vacation packages in Central Illinois

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥378,106
per person
Oct 3 - Oct 8
found 6 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
¥566,827
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥433,374
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.

Reviewed on Aug 8, 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥487,982
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
Delicious breakfast, perfect location, friendly staff!

Reviewed on Aug 8, 2026

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

Downtown Chicago
¥425,110
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,360 reviews)
A total disappointment for birthday week. The staff is rude, unfriendly and very unhelpful. The best employees were the cleaning staff. I sent several emails prior to checking in about down pillows needing removed, they didn’t comply, caused an asthma attack, acted like I was a bother when I called asking for the pillows to be replaced and the gentleman who brought them brought 2 foam and 2 more down, all out of pillowcases. I asked to speak to a manager twice, never got to. We had a suite and it is not worth the hype, blocked views and the wallpaper was all scuffed up. In a city like Chicago you have many choices, you can choose better.

Reviewed on Aug 7, 2026

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5* Ski vacations in Central Illinois

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥487,012
per person
Oct 3 - Oct 8
found 6 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Great experience!

Reviewed on Aug 7, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
¥566,827
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
¥583,301
per person
Oct 3 - Oct 8
found 6 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
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4 Night Ski vacations in Central Illinois

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥258,259
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
¥271,031
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥264,027
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.