Chicago Ski Holidays
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Top flight + Ski hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
4 Night Ski holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Extended Stay America Suites Chicago O'Hare Allstate Arena
O'Hare
per person
15 Aug - 18 Aug
found 20 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
7.4/10 Good! (1,000 reviews)
Wendy at the front desk is truly amazing! She was incredibly helpful to us. Our room was clean.
Reviewed on 18 Jun. 2025
Top Ski Chicago Hotels
Victorian Rose Garden
314 Washington Street, Algonquin, IL
Stay at this 3-star B&B in Algonquin. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Buffalo Park Forest Preserve and Algonquin Lakes ...
9.8/10 Exceptional! (87 reviews)
"It's a lovely property, and Sherry is a very nice host. Breakfast was delicious. Several restaurants are within a short walk."
Reviewed on 6 Feb. 2025
Hyatt Regency Lisle near Naperville
1400 Corporetum Drive, Lisle, IL
Stay at this 3.5-star business-friendly hotel in Lisle. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.4/10 Good! (1,002 reviews)
"Good experience."
Reviewed on 29 Jun. 2025
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! (927 reviews)
Good value and comfortable
"Overall, the rooms are nice and very comfortable. You are best going down early for breakfast otherwise it gets a little bit dry, but there is hapes to choose from or pretty much anyone including healthier options. My only complaint would be the air conditioning units. They are very very loud and ..."
Reviewed on 3 Jul. 2025
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.