Chicago Ski Holidays
Book a Ski Hotel + Flight or Car together to unlock savings
Better together
Save up to ₹43,962 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top flight + Ski hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Lisle Naperville
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (1,033 reviews)
The stay was great but there was a surprise charge when we got there. Expedias website said the hotel was pet friendly but failed to mention the $100 non-refundable pet fee that was attached.
Reviewed on 29 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 Wi-Fi 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 Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.4/10 Good! (1,001 reviews)
"Good experience."
Reviewed on 29 Jun 2025
Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG
2595 Bunker Hill Dr, Algonquin, IL
Stay at this business-friendly hotel in Algonquin. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
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.
More Holiday Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.