Chicago Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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 Chicago
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Lisle Naperville
Price was ￥277,294, price is now ￥268,123 per person
￥268,123
per person
Mar 14 - Mar 17
just found
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
7.8/10 Good! (1,192 reviews)
Bed was comfortable. The room was clean but outdated. The bathroom was nice but low water pressure in the shower. Nice lobby and bar. Breakfast buffet was not that great.
Reviewed on Jan 12, 2026
3 Night Ski vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Lisle Naperville
Price was ￥277,294, price is now ￥268,123 per person
￥268,123
per person
Mar 14 - Mar 17
just found
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
7.8/10 Good! (1,192 reviews)
Bed was comfortable. The room was clean but outdated. The bathroom was nice but low water pressure in the shower. Nice lobby and bar. Breakfast buffet was not that great.
Reviewed on Jan 12, 2026
4 Night Ski vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Lisle Naperville
Price was ￥218,010, price is now ￥206,462 per person
￥206,462
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (1,192 reviews)
Bed was comfortable. The room was clean but outdated. The bathroom was nice but low water pressure in the shower. Nice lobby and bar. Breakfast buffet was not that great.
Reviewed on Jan 12, 2026
ACME Hotel Company
Downtown Chicago
Price was ￥284,922, price is now ￥277,820 per person
￥277,820
per person
Feb 21 - Feb 25
found 19 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (1,868 reviews)
Staff was awesome!!! 5 stars for teamwork. What one person didn’t know, another stepped in quickly to help. Rooms are small, view was horrible but room was only used for sleeping after a big party.
Reviewed on Jan 15, 2026
Top Ski Chicago Hotels
Victorian Rose Garden
314 Washington Street Algonquin IL
Stay at this B&B in Algonquin. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Buffalo Park Forest Preserve and Algonquin Lakes Trailhead ...
9.8/10 Exceptional! (90 reviews)
The space was beautiful and Sherry was the sweetest hostess! We loved every minute of our stay!
Reviewed on Oct 30, 2025
Hyatt Regency Lisle near Naperville
1400 Corporetum Drive Lisle IL
Book a stay at this business-friendly hotel in Lisle. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
7.6/10 Good! (1,092 reviews)
Wonderful ambience!
Reviewed on Jan 4, 2026
Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG
2595 Bunker Hill Dr Algonquin IL
Book a stay at this business-friendly hotel in Algonquin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,002 reviews)
Easy check in, nice gift bag with waters and cookies. ADA room as requested. Nice stay.
Reviewed on Jan 11, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
