Northwest Chicago Ski Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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 Northwest Chicago
- Candlewood Suites Elgin by IHG
Sep 4 - Sep 7Candlewood Suites Elgin by IHG + Flight
Elgin2 nights2.5 star property8.6/10 - Excellent (392 reviews)"Room was not clean. There was food on the floor when we arrived. There was water on the floor from under the dishwasher. Not sure if it was leaking as we did not use it."Reviewed July 12, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop MDW - ATL • Nonstop$303$300found 1 day agoper traveler - Residence Inn by Marriott Chicago Bloomingdale
Sep 23 - Sep 28Residence Inn by Marriott Chicago Bloomingdale + Flight
Bloomingdale5 nights3.0 star property8.4/10 - Very Good (384 reviews)"Excellent staff"Reviewed June 14, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Comfort Suites Elgin Northwest
Oct 9 - Oct 12Comfort Suites Elgin Northwest + Flight
Elgin3 nights2.5 star property8.0/10 - Very Good (1,005 reviews)"Property, room and staff were excellent. I had an accessible room on the first floor. The shower was barrier free with a moving wand. I would encourage lift bars at the toilet and in the shower for safety purposes. Also install towel bars. I had to throw towels over the shower curtain rail. The bed height was lower and that was helpful. Air system kept the room comfortable in the humid hot weather. The breakfast was delicious and plentiful and well maintained by staff. It was a pleasant..."Reviewed July 18, 2026Roundtrip • Dallas (DFW) - Chicago (ORD)DFW - ORD • Nonstop MDW - DFW • Nonstop$468$390found 1 day agoper traveler - Country Inn & Suites by Radisson, Hoffman Estates, IL
Sep 3 - Sep 5Country Inn & Suites by Radisson, Hoffman Estates, IL + Flight
Hoffman Estates2 nights3.0 star property7.8/10 - Good (1,002 reviews)"Great"Reviewed July 18, 2026Roundtrip • New York (NYC) - Chicago (ORD)JFK - ORD • Nonstop ORD - JFK • Nonstop$324$317found 1 day agoper traveler
Discover the most popular places to visit in Northwest Chicago
What to do in Northwest Chicago
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour
Top Ski Northwest Chicago Hotels
Best Western Plus Elgin - Chicago
Best Western Plus Elgin - Chicago
Country Inn & Suites by Radisson, Hoffman Estates, IL
Country Inn & Suites by Radisson, Hoffman Estates, IL
Comfort Suites Elgin Northwest
Comfort Suites Elgin Northwest
Candlewood Suites Elgin by IHG
Candlewood Suites Elgin by IHG
Lexington Inn & Suites NW Chicago Elgin
Lexington Inn & Suites NW Chicago Elgin
Residence Inn by Marriott Chicago Bloomingdale
Residence Inn by Marriott Chicago Bloomingdale
Extended Stay America Suites Chicago Elgin West Dundee
Extended Stay America Suites Chicago Elgin West DundeePlanning your Northwest Chicago ski vacation
What are some things I should consider when booking a Northwest Chicago ski trip package?
Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.
How can I find cheap Northwest Chicago ski packages?
Right now, ski trips start at just $300. Prices and availability are subject to change. Additional terms may apply.
Can I book a beginner ski package in Northwest Chicago?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Northwest Chicago. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.
How much does a ski trip to Northwest Chicago cost?
Sensational ski trips to Northwest Chicago start from $300. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.
When’s the best time of year to plan a ski trip to Northwest Chicago?
The best time to hit the slopes in Northwest Chicago depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.
Can I book Northwest Chicago ski packages with airfare?
Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.
Can I book a Northwest Chicago ski trip with free cancellation and/or flexible dates?
Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.
Why should I book a ski package in Northwest Chicago with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Northwest Chicago ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.