Best Group Road Trips from Chicago

Chicago is a perfect launch point for a group road trip — highways head out in every direction, and a rental van keeps everyone together for the ride. Whether you’ve got a weekend or two weeks, here are some of the best group trips to take from the city.

Quick getaways (a few hours out)

For a short trip, aim for the Lake Michigan shoreline and the beach towns of Michigan and Indiana, or head north to the Wisconsin Dells for family fun. Both are easy drives that pack a lot into a weekend.

Long-weekend road trips

With a few days, point the van toward Nashville for music and food, the Great Smoky Mountains for the outdoors, or St. Louis and the Ozarks. Far enough to feel like a real trip, close enough to keep the driving easy.

Bucket-list adventures

Got a week or more? Chase the sun to Florida (Tampa and Miami) in winter or over spring break, explore New York and the East Coast, or head west to Yellowstone and Montana or Arizona’s national parks. These are the trips a comfortable van makes possible.

Cross the border into Canada

Unlike many big rental chains, we let you take our vans into Canada — so Toronto, Niagara Falls, and beyond are all on the table for your group.

Why a van beats flying or driving separately

One van keeps the group together, splits the cost across everyone, and carries all the luggage and gear — no coordinating separate cars, no pricey group flights. With two additional drivers free (three drivers in total) and no special license needed for personal use, the road trip is the easy part.

Which van should you pick?

For comfort on a long road trip, the 15-passenger Mercedes-Benz Sprinter or the luxury Golden Chariot; for value, the 15-passenger Ford Transit. See the full fleet to pick your ride.