Where do Chicagoans go when they want to get away for a weekend? These are the best Midwest getaways, destinations that are a quick and easy drive, or train ride, from Chicago.
The Best Midwest Getaways
New Buffalo
I know, I cannot stop talking about New Buffalo! I visited for the first time in November 2024, and I am currently planning my fifth trip back to this charming town on the shores of Lake Michigan.
New Buffalo is an ideal Midwest getaway for several reasons. It's just an hour and fifteen minutes from Chicago. You can drive or take the train (the station is downtown and the town is walkable - no car needed). The Harbor Grand offers a great spa, breakfast in bed, and lovely dining options, making it perfect for couples seeking a quiet escape from the city. The Marina Grand has large room types perfect for families.
The town has a wonderful beach, shops, and fun restaurants. I have gone alone to relax, brought my family, and hosted mom's retreats here.
Read more about Things to do in New Buffalo
Grand Geneva
This resort was the original Playboy Club. Today, it is a family-friendly destination with indoor and outdoor pools, golf, multiple restaurants, and a ski hill.
Grand Geneva is one of our go-to spots for a weekend away. The drive is just under an hour and a half, and there are plenty of activities and dining options on site. Timber Ridge is an indoor water park resort and sister property to Grand Geneva. When we have visited in the winter, we have split time between the ski hill and Timber Ridge.
Read more about Grand Geneva here.
Milwaukee
Milwaukee is just 90 minutes from Chicago, and you have the option of driving or taking the train. I have been to this smaller city on trips with my husband and with our daughter. When I visited with my husband, we toured breweries, including the Historic Pabst Brewery, ate at the Public Market, and visited local shops. It was fun exploring somewhere new for a weekend.
Last year, I decided to bring my five-year-old to Milwaukee for a quick Spring Break trip. Milwaukee was easy and fun! We went with another Mom and kiddo, and it was great exploring new-to-us museums, playgrounds, and restaurants. The kids are still talking about SafeHouse, a spy-themed restaurant with a scavenger hunt.
The highlight of Milwaukee's summer schedule is Summerfest, a massive 9-day music festival. The 2026 lineup includes Garth Brooks, Jelly Roll, Muse, and Post Malone.
Read more about Things to Do with Kids in Milwaukee here.
Kohler
Yes, the same Kohler that makes your faucets. The American Club, in Kohler, Wisconsin, was originally built as housing for Kohler's immigrant workers. In the 1970s, it was converted into a hotel. Today, the American Club is a luxurious resort with a top-tier spa and dining options.
Activities include golf, yoga, and indoor cycling. The dining options include the incredible brunch buffet at The Wisconsin Room, a casual pub with exceptional cheese curds, and a cozy wine bar.
Kohler Food and Wine is an annual event that takes place each fall and features presentations from celebrity chefs and tasting events. I went several years ago and loved it!
Read more about Kohler and the American Club here.
