Places to Visit from Chicago during the Winter Season

27 Aug-2024

Winter is a great time to get out of Chicago — whether you’re chasing snow or escaping it. Here are the best winter destinations to reach by van, plus tips to drive there safely.

Escape the cold: Florida & Orlando

For sun and warmth, point the van south to Florida — beaches, and Disney Orlando for the families. It’s a long, easy interstate drive and a favorite winter escape for Chicago groups.

City trips: New York & New Jersey

For a winter city getaway, New York and New Jersey deliver holiday lights, shows, and sights — all reachable in one van with the whole group together.

Embrace the snow: Wilmot Mountain & Madison

Prefer winter fun? Wilmot Mountain is an easy ski and snowboard trip, and Madison, Wisconsin makes a cozy cold-weather weekend.

Drive safely in winter

Check the van’s condition and pack an emergency kit, plan your route, and drive slowly and smoothly with extra following distance. Stay in control, keep up with the forecast, and take breaks. Our Mercedes-Benz Sprinters add Crosswind Assist, Lane Keeping Assist, and automatic emergency braking for winter confidence.

Go wherever winter takes you

Because we’re Illinois-based, you can drive our vans anywhere across the USA and into Canada — sun or snow — with just a regular license and up to three additional drivers free.

Which van should you pick?

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