6 Easy Weekend Trips from Chicago
Chicago is a great city, but even Chicagoans need a break from it. Luckily, the Midwest around it is full of easy escapes: lake towns, sand dunes, a brewery city, a historic river town and plenty of cozy B&Bs.
In this guide
None of these require a flight, and two don’t even need a car. Here are six easy weekend trips from Chicago, all within about three hours.
1. Milwaukee, Wisconsin
Milwaukee is about 90 minutes north, and the easiest way there is the Amtrak Hiawatha train, which takes about 90 minutes and drops you downtown. No traffic, no parking. It’s a very easy weekend.
Milwaukee is underrated. Walk the Riverwalk, see the Milwaukee Art Museum, whose white roof opens and closes like wings, and tour a brewery (or several). The Third Ward is great for food and shops. Don’t leave without a Friday fish fry and some cheese curds. It’s the law here, or at least it feels like it.
2. Indiana Dunes National Park
Indiana Dunes is only about an hour from downtown, and it feels like a different world. Fifteen miles of sandy Lake Michigan beaches, tall dunes and quiet forest trails. On a clear day, you can see the Chicago skyline across the water.
The South Shore Line train runs from downtown Chicago and stops near the park, so you can go car-free. Climb the 3 Dune Challenge at Indiana Dunes State Park, which is tougher than it sounds, then cool off in the lake. In summer, it’s a proper beach vacation, close to home.
3. Madison, Wisconsin
Madison is about two and a half hours northwest, and it’s built on a narrow strip of land between two lakes. The State Capitol sits right in the middle, and its dome is actually taller than the one in Washington, DC.
On Saturday mornings from spring to fall, the Dane County Farmers’ Market wraps around the Capitol Square. It’s one of the biggest in the country. Then walk State Street, the lively pedestrian street down to the University of Wisconsin campus, and finish at the Memorial Union Terrace with a beer and a lake view.
4. Lake Geneva, Wisconsin
Lake Geneva is about 90 minutes northwest, and it’s been Chicago’s lakeside retreat since the 1870s. Wealthy Chicago families built huge summer mansions around the lake, and many of them are still there.
The best way to see them is the 21-mile public shore path, which runs right past their lawns. You can walk any section you like. Or take a boat tour, including one where the mail is still delivered by jumping onto piers from a moving boat. In winter, the town hosts an ice castle and a snow-sculpting festival.
5. Galena, Illinois
Galena is about two hours and 45 minutes west, near the Mississippi River, and it’s one of the prettiest small towns in the Midwest. Its brick Main Street looks almost unchanged since the 1800s, when Galena was a booming lead-mining town.
Ulysses S. Grant lived here, and you can visit his home. But mostly, Galena is about wandering: antique shops, wine-tasting rooms, cozy restaurants and lots of B&Bs. Fall is especially lovely, when the hills turn orange. It’s a great romantic weekend, and it’s very walkable once you’re there.
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6. Southwest Michigan: Saugatuck and St. Joseph
Across the lake, southwest Michigan is full of charming beach towns. Saugatuck, about two and a half hours away, is the artsy one, with galleries, an old chain ferry and Oval Beach, which is surrounded by dunes.
St. Joseph, closer at about 90 minutes, has a classic Lake Michigan lighthouse at the end of a long pier. It’s a great place to watch the sunset. Along the way, you’ll pass orchards, farm stands and wineries. One tip: Michigan is on Eastern Time, an hour ahead of Chicago.
How to plan your weekend
For a car-free trip, pick Milwaukee or the Indiana Dunes. Both are an easy train ride from downtown. For the others, renting a car is much easier. Leave Friday at lunchtime or after 7 p.m. to avoid the worst of the traffic, which can be brutal, especially heading into Wisconsin in summer.
Book ahead in summer and fall. These towns are small, and the nice B&Bs fill up on weekends.
Can you do them as day trips?
A few, yes. The Indiana Dunes, Milwaukee, Lake Geneva and St. Joseph are all close enough for a long day out. Madison, Galena and Saugatuck really deserve a night, though. The drive is long enough that you’d spend most of the day in the car, and the evenings are half the charm. Honestly, an overnight anywhere on this list feels like a proper vacation.
When to go
Summer is beach season, perfect for the Dunes, Lake Geneva and Michigan. Fall is beautiful everywhere, especially Galena. Winter is quiet but cozy, and Lake Geneva’s winter festivals are fun. Spring can be gray and muddy, honestly, but cheaper.
Where to stay
Each of these places has its own style. Milwaukee has stylish downtown hotels in old industrial buildings, many in the Third Ward. Madison has good hotels near the Capitol Square, so you can walk everywhere. Lake Geneva has big resorts and lake-view inns, and they’re pricier on summer weekends.
Galena is B&B country. Many are in historic mansions, and some come with a fireplace and a huge breakfast. In southwest Michigan, look for cottages, small inns and vacation rentals near the beaches. For the Indiana Dunes, there are campgrounds in the national and state parks, plus small hotels in nearby towns like Chesterton. If you’re going car-free, stay close to the train stations.
Prices drop a lot outside of summer and fall, and weekday stays are often much cheaper too.
Common questions
What’s the best weekend trip from Chicago without a car?
Milwaukee by Amtrak, or the Indiana Dunes on the South Shore Line.
What’s the most romantic getaway from Chicago?
Galena, with its historic Main Street and cozy B&Bs.
How far is Lake Geneva from Chicago?
About 90 minutes by car.
Is Indiana Dunes worth visiting?
Yes. It’s close, beautiful and has great Lake Michigan beaches.
Is Michigan on a different time zone from Chicago?
Yes, most of it is on Eastern Time, an hour ahead.
