Chicago is one of the best road trip bases in the country, and most people never use it. Within two hours you can reach dunes, lakeshore, wine country and a proper river gorge. Within a day's drive you can reach Nashville, Niagara Falls, the Smokies or the Upper Peninsula. What stops most groups is not distance — it is the vehicle. Splitting eight people across two cars turns a trip into a logistics exercise, and a single van turns the drive itself into part of the holiday.
Here are the routes we see our vans go out on most often, roughly in order of distance, with honest notes on what each one is actually like with a full vehicle.
The closest genuine escape from the city. Fifteen miles of Lake Michigan shoreline with proper dunes behind it, a national park since 2019, and a drive short enough that you can leave after breakfast and still get a full beach day. West Beach and Porter Beach are the easy choices with a group; the Three Dune Challenge is the one everybody photographs and nobody enjoys halfway up.
With a van: ideal. The trunk swallows coolers, umbrellas, chairs and the mountain of towels that a group of eight generates. Summer weekends fill the parking lots early — arrive before ten or after three.
Illinois surprises people here. Eighteen canyons cut into sandstone along the Illinois River, with waterfalls that run hard in spring and freeze into ice columns in January. The trails are short and manageable for mixed-age groups, which makes it one of the few outdoor days that works with grandparents and small children in the same party.
With a van: parking is the whole problem here on weekends. One vehicle in the lot instead of two doubles your odds of getting in without circling.
A lake resort town that has been Chicago's weekend escape for over a century. The Shore Path walks past the historic mansions, the boat tours are genuinely good, and in winter the town leans hard into the season with ice castles and a snow sculpting competition.
With a van: the classic single-overnight group trip. Rent a house, put everyone in one vehicle, and the driving is short enough that nobody gets restless.
Cross into Michigan and the character of the lake changes completely: soft sand, dune-backed beaches, small towns with good food. Saugatuck and Douglas are the walkable pair; Holland has the Dutch-heritage tulip festival in May; South Haven and Grand Haven are quieter and cheaper. Oval Beach outside Saugatuck is regularly rated among the best freshwater beaches in the country and deserves it.
With a van: the drive skirts the bottom of the lake through Gary, which is heavy at rush hour — leave before seven or after ten. Remember the time zone change: Michigan is an hour ahead, and forgetting it has cost more than one group a dinner reservation.
A preserved 19th-century lead-mining town in the northwest corner of the state, sitting in genuinely hilly country that does not look like Illinois at all. Main Street is a single walkable strip of brick buildings, and the surrounding Driftless Area has the best autumn colour within striking distance of Chicago.
With a van: a strong shoulder-season choice. October weekends are busy; book accommodation well ahead.
The waterpark capital of the world, and a trip that exists almost entirely for children. Behind the waterparks there is a real river gorge with sandstone formations worth a boat tour, but nobody under twelve will care. Noah's Ark is the largest outdoor park; Kalahari and the Wilderness are the big indoor resorts, which makes this a viable winter trip too.
With a van: practically designed for it. Families travel here in groups, luggage volume is high because of the swimming gear, and three hours is right at the edge of what works without an overnight stop.
A long peninsula between Green Bay and Lake Michigan, with about 300 miles of shoreline, eleven lighthouses, cherry orchards and five state parks. Peninsula State Park is the obvious base; Cave Point County Park is the photograph everyone comes home with. It is the closest thing the Midwest has to coastal New England.
With a van: a proper long weekend, minimum. The drive up through Milwaukee and Green Bay is easy interstate, and the peninsula itself needs a vehicle — there is no meaningful public transport once you are there.
Long, and worth it. Drive to Mackinaw City, park the van, and take the ferry to an island where cars have been banned since 1898 — everything moves by bicycle, horse or foot. Traverse City and the Sleeping Bear Dunes are on the same route if you want to make it a full week.
With a van: six hours is where seat comfort stops being a detail. This is also the trip where full-size vans earn their rate: with a group, you are carrying bikes, coolers and a week of luggage.
The most popular long-haul run out of Chicago, straight down I-65 through Indianapolis and Louisville. Music, food, and a city compact enough that a group can leave the vehicle parked for two days. Mammoth Cave sits almost exactly on the route if you want to break the drive.
With a van: the economics get very persuasive here. Two cars to Nashville and back means two lots of fuel and two lots of parking, and everyone arrives having had a different trip.
The most visited national park in the United States, and a genuine full-week destination. Gatlinburg and Pigeon Forge as bases, Cades Cove and Clingmans Dome as the must-drives. Nine hours is a real day behind the wheel — split the driving, or overnight in Louisville or Lexington on the way down.
Whichever route you pick, the vehicle decision comes first. Our Chicago minivan and passenger van rentals cover daily, weekly and monthly bookings, with pickup in the city or delivery to O'Hare and Midway.