Illinois Ski Vacations
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Top Ski vacation packages in Illinois
3 Night Ski vacations in Illinois
4 Night Ski vacations in Illinois
Extended Stay America Suites Chicago O'Hare Allstate Arena
Reviewed on Jan 5, 2026
Planning your Illinois ski vacation
What are some things I should consider when booking a Illinois 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 Illinois ski packages?
Right now, ski trips start at just $409. Prices and availability are subject to change. Additional terms may apply.
Can I book a beginner ski package in Illinois?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Illinois. 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 Illinois cost?
Sensational ski trips to Illinois start from $409. 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 Illinois?
The best time to hit the slopes in Illinois 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 Illinois 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 Illinois 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 Illinois with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Illinois ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.
Top Ski Illinois Hotels
Chestnut Mountain Resort
This is one of our favorite family vacations. Everything you need is in one place - great slopes to ski at, wonderful accommodations and friendly staff.
Reviewed on Jan 20, 2026
Country Inn & Suites by Radisson, Galena, IL
Very clean room. Quiet and comfortable. Very friendly staff. Good breakfast. Easy to find
Reviewed on Jan 23, 2026
Fabulous Home Away From Home, Fabulous Home Away From Home - 4 Bdr - With Hot Tub!
This was an exceptional home away from home. We thouroughly enjoyed the screened in porch for meals as well as visiting and playing cards in the evening. It was in a beautiful location and the siblings and spouses had a great time reconnecting. The host/manager was very accommodating and answered ...
Reviewed on Sep 27, 2025
