Most visitors to Chicago never leave the city, and I understand why. There’s the architecture, the lakefront and more deep-dish pizza than any one person should eat. But hire a car for a couple of days and a very different Midwest opens up. Think dunes, waterfalls, sleepy brick towns and long, empty lake views.
The best part is that none of it is very far. These ten trips all work as a weekend away, and a few are easy enough for a single day.
Before You Set Off
American distances can catch you out, even on a short trip. Roads are long and straight, and petrol stations can be few and far between once you leave the suburbs. So it pays to make sure the car is in good shape before you go.
If you’re driving your own car, or borrowing a friend’s, get it checked a week or so before you leave. An oil change is the job most people forget. If you’re setting off from the North Shore, an oil change at Old Orchard Nissan in Skokie is a handy last stop before the motorway. It’s also worth a quick look at the tyres, wipers and screen wash, as Midwest roads are dusty in summer and salty in winter.
One more thing. Most of the motorways around Chicago are toll roads, and there are no booths to pay at. Cameras read your number plate, and you pay online afterwards. If you’ve hired a car, ask the rental company how they handle it, as some add a fee on top.
1. Indiana Dunes National Park
It’s hard to believe this is only an hour from the Loop. Huge dunes rise straight up from Lake Michigan, and on a clear day you can see the Chicago skyline across the water. It’s an easy first trip, with beaches for lazing and trails for those who want to work for the view.
A standard pass for a private car costs $25 and covers everyone inside for up to seven days. If you arrive on foot or by bike, it’s $15 per person, and an America the Beautiful pass covers entry too. You can check the latest fees on the National Park Service website. The state park next door is run separately and charges its own fee, which surprises a lot of people.
2. Starved Rock State Park
I didn’t expect waterfalls in Illinois, a state better known for being flat. Yet about 90 minutes south-west of the city, Starved Rock hides a series of sandstone canyons. The falls are at their best in spring. In a cold winter, they freeze into great columns of ice.
Entry and parking are free. That makes it very popular, so on a sunny weekend try to arrive before mid-morning. And leave the nice shoes at home, as the trails can get muddy.
3. Lake Geneva, Wisconsin
This is where wealthy Chicagoans built their summer homes in the late 1800s, and many of those grand mansions still line the water. The town itself is a little touristy, but the lake is lovely. A boat tour is the easiest way to see the houses.
For something more unusual, walk a stretch of the 21-mile shore path. It runs right past the mansions and through their gardens. It’s free and open to everyone, but it’s also people’s private property, so do keep to the path.
4. Milwaukee, Wisconsin
Milwaukee often gets overlooked, which is a shame. It’s 90 minutes up the lake and makes a relaxed city break. The old warehouses of the Historic Third Ward are now full of shops and restaurants, and the brewing history is everywhere. Even if art isn’t your thing, the Milwaukee Art Museum is worth a visit just to see the building.
The city has a festival on almost every summer weekend. That’s great fun, but it also pushes up hotel prices, so check the calendar before you book.
5. Galena, Illinois
Galena is about three hours west, close to the Mississippi. In the mid-1800s it was a busy river town, and it has barely changed since. Main Street is lined with red-brick buildings, independent shops, wine tasting rooms and cafés. It’s the sort of place you come to wander and do very little, and that’s the point.
The town is built into a hillside, so expect a few steep steps. It’s especially pretty in autumn, when rooms get booked up weeks ahead.
6. Madison, Wisconsin
Wisconsin’s capital sits on a narrow strip of land between two lakes, two and a half hours from Chicago. It’s a university town, so it feels young and lively, but it’s also green and very easy to get around on foot or by bike.
The domed State Capitol is the centrepiece, and the guided tours are free. If you’re there on a Saturday between spring and autumn, a huge farmers’ market takes over the square around it. Go hungry.
7. Saugatuck, Michigan
Saugatuck is an arts town on the Michigan side of the lake, around two and a half hours away. There are galleries, ice cream parlours and a slightly bohemian feel. Climb the steps up Mount Baldhead for a view over the town, then head down to Oval Beach, which is regularly named one of the best in the country.
In summer, parking at the beach costs $15 a car. Or skip the car park and call the local Interurban bus, which will take you there for $1. Outside the summer season, parking is free.
8. Route 66 to Springfield, Illinois
Few things feel more American than Route 66, and it starts right in downtown Chicago. You won’t drive all 2,400 miles to Los Angeles in a weekend, but the first stretch to Springfield is about three hours. Along the way you’ll find old diners, vintage petrol stations and some wonderfully odd roadside giants.
Springfield was Abraham Lincoln’s home town, and his house is now run by the National Park Service. Tours are free, but you need a ticket from the visitor centre on the day. They go on a first-come, first-served basis, so it’s worth getting there early.
9. Door County, Wisconsin
Door County is a long, thin peninsula poking out into Lake Michigan, about four hours from the city. It’s often called the Cape Cod of the Midwest, with lighthouses, cherry orchards and little fishing villages. Look out for a traditional fish boil, where the cooking ends with a dramatic burst of flames.
At four hours each way, this one is best saved for a long weekend. Bear in mind that state parks here charge a daily fee per car, and it’s higher for out-of-state plates. Plenty of places also close or cut their hours in winter.
10. Mackinac Island, Michigan
I’ve saved the furthest for last. It’s a five-and-a-half to six-hour drive to the ferry, but Mackinac Island feels like nowhere else. Cars have been banned here for over a century, so you get around by bike, on foot or in a horse-drawn carriage. The island is also famous for its fudge, and you’ll smell the shops before you see them.
You leave the car on the mainland in Mackinaw City or St. Ignace and take the ferry across. A return ticket costs around $37 to $39 per adult, and in summer it’s worth booking ahead.
Final Thoughts
Chicago is a fantastic city, but some of the best moments of a visit can happen outside it. Start with something close, like the Dunes or Starved Rock. Then, if you catch the bug, save Door County or Mackinac Island for a long weekend. Either way, the drive is half the fun.
