Chicago Ski Vacations

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.

Right now, ski trips start at just $271. Prices and availability are subject to change. Additional terms may apply.

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in 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.

Sensational ski trips to Chicago start from $271. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

The best time to hit the slopes in 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.

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.

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.

Simple search and fantastic filters make it easy to find, build, and book your dream Chicago ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.