Northwest Chicago Ski Vacations
Book a Hotel + Flight or Car together to unlock savings
Top Ski vacation packages in Northwest Chicago
- Comfort Suites Elgin Northwest
Aug 21 - Aug 23Comfort Suites Elgin Northwest + Flight
Elgin2 nights2.5 star property8.0/10 - Very Good (1,000 reviews)"The one main issue I had was the room was advertised as a King Size bed, but it was only a Queen size bed."Reviewed July 21, 2026Roundtrip • New York (NYC) - Chicago (ORD)LGA - MDW • Nonstop MDW - LGA • Nonstop$381$346found 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 (386 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Extended Stay America Suites Chicago Elgin West Dundee
Oct 9 - Oct 11Extended Stay America Suites Chicago Elgin West Dundee + Flight
West Dundee2 nights2.5 star property6.4/10 - (621 reviews)"Breakfast?! Terrible, was basically some muffins and an empty coffee dispenser. With that effort they should just not offer breakfast. The facilities are dated and could use better upkeep (lights out, broken, etc.) Staff was nice but everything else makes me not want to book here again."Reviewed July 21, 2026Roundtrip • New York (NYC) - Chicago (ORD)LGA - MDW • Nonstop ORD - LGA • Nonstop$557$544found 1 day agoper traveler - Lexington Inn & Suites NW Chicago Elgin
Oct 9 - Oct 11Lexington Inn & Suites NW Chicago Elgin + Flight
Elgin2 nights2.5 star property5.0/10 - (491 reviews)Roundtrip • New York (NYC) - Chicago (ORD)LGA - MDW • Nonstop ORD - LGA • Nonstop$443$435found 1 day agoper traveler - Best Western Plus Elgin - Chicago
Sep 2 - Sep 6Best Western Plus Elgin - Chicago + Flight
West Dundee4 nights3.0 star property8.4/10 - Very Good (1,019 reviews)"Check in was quick and easy. The staff was efficient and quick getting the line of guests checked in. The Best Western Room was clean and smelled fresh when we arrived. For a hot summer day, the air conditioning was working great. There was a smokey sky lingering over the area, but the room was fresh and no odor from outside. My granddaughters used the pool. Not overly large, but they had fun jumping in and swimming their races back and forth. We didn't have breakfast at the hotel as we..."Reviewed July 22, 2026Roundtrip • New York (EWR) - Chicago (ORD)EWR - ORD • Nonstop MDW - EWR • 1 stop$497$489found 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 $346. 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 $346. 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.