Looking for a weekend adventure or quick road trip from Chicago? Check out these six amazing getaways!
Chesterton, Indiana
For outdoor enthusiasts, Chesterton offers hiking, bike trails, and beautiful beaches. From Indiana Dunes to the Prairie Duneland Trail, there are plenty of things to do! Check out Township History Museum, Chesterton Art Center as well as local galleries and antique markets.
Top things to do in Chesterton:
- Township History Museum
- Indiana Dunes National Park
- Running Vines Winery
Distance from Chicago: 47 miles
New Buffalo, Michigan
New Buffalo is a charming Lake Michigan beach town. Venture to New Buffalo for local wineries, breweries, vintage & antique shops, and villages of the southern lakeshore.
Top things to do in New Buffalo:
- New Buffalo MI Beach
- Eat dinner at The Stray Dog
- Warren Dunes State Park
Distance from Chicago: 70 miles
Lake Geneva, Wisconsin
Lake Geneva is a popular resort city in Southeastern Wisconsin. Enjoy local beaches, cultural events and festivals, and a variety of restaurants.
Top things to do in Lake Geneva:
- Safari Lake Geneva
- Geneva Lake Museum
- Kishwauketoe Nature Conservancy
Distance from Chicago: 83 miles
Winamac, Indiana
If you’re looking for a memorable day trip, Winamac might be for you! This small town offers visitors the perfect combination of scenic outdoors and downtown family‑friendly attractions. Spend the day at Tippecanoe River State Park then head downtown for a slice of pizza and some local beer at Tippy’s.
Top things to do in Winamac:
- Kersting’s Cycle Center and Museum
- Tippecanoe River State Park
- Panhandle Pathway
Distance from Chicago: 103 miles
Galena, Illinois
Galena is a Midwestern gem that offers local flavor, rich history, and rolling vineyards. It’s famous for its preserved 19th‑century buildings and ancient ceremonial sites. Walk down Main Street and shop at over 125 local boutique shops.
Top things to do in Galena:
- Ulysses S. Grant Home
- Chestnut Mountain Resort
- Galena Cellars Winery & Vineyard
Distance from Chicago: 149 miles
South Haven, Michigan
South Haven is a port city filled with beautiful beaches, old-fashioned charm, eclectic restaurants, and award-winning wineries. This beach town escape is perfect for couples, families, and nature lovers – there is something for everyone.
Top things to do in South Haven:
- South Haven Lighthouse
- The Kal-Haven Trail
- Cogdal Vineyards
Looking for a place to stay in South Haven? We recommend this vacation rental home!
Distance from Chicago: 47 miles
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