Winter Road Trips From Chicago: Top Ski Destinations and the Best Vans for Snow Travel

29 Dec-2025

Chicago is a perfect launch point for a ski trip, and a rented van keeps the whole group — plus all the gear — together for the drive. Here are the best ski destinations to reach, and how a van makes it easy.

Nearby slopes (Midwest)

For a quick trip, Wilmot Mountain and Alpine Valley Resort in Wisconsin are easy drives, as are Cascade Mountain in the Wisconsin Dells and Granite Peak in Wausau. Over in Michigan, Boyne Mountain and Boyne Highlands are worth the miles.

Big-mountain trips (out west)

Ready for the real thing? Colorado’s Vail, Breckenridge, and Keystone, and Utah’s Park City, Alta, and Snowbird are bucket-list slopes — a longer haul, but unforgettable with the group.

Why the right vehicle matters

Ski trips mean snow, gear, and a full group. Our Mercedes-Benz Sprinters add Crosswind Assist, Lane Keeping Assist, and automatic emergency braking for winter roads, plus room for skis, boards, and bags.

Value for the group

A Ford Transit keeps a ski weekend budget-friendly, while a Sprinter adds comfort for the long drive. Either way, one van, one fuel bill, split across everyone.

Go the distance

Because we’re Illinois-based, you can drive our vans to the slopes anywhere across the USA and into Canada — no special license needed for personal use, and up to three additional drivers free.

Which van should you pick?

For comfort, the 15-passenger Mercedes-Benz Sprinter; for value, the 15-passenger Ford Transit. Browse the full fleet.