Top 5 Day Trip Ideas from Chicago



Whether you live in Chicago or just passing through, there are plenty of amazing places to visit if you want to get out of the city for the day. You can explore the quirks of nearby cities and counties, or get lost in an area of natural beauty. Chicago works great as a hub in the Midwest, connected by various transport options. You can get to both urban and rural areas of Illinois, Michigan, and Wisconsin easily. Here are the top five-day trip ideas from Chicago.

Fennville, MI

Fennville is a haven for fruit lovers as it’s full of famous orchards. The most popular time to visit is for the fall harvest, but you can also sample some amazing things in the summer. Peaches and cherries are ripe for the picking and you can learn about their cultivation. You can also find quaint bakeries serving pies made from the local fruit and traditional timbered cider houses. It’s a good idea to make reservations for tastings online, especially if you go during the busy season.

Rockford, IL

The natural landscape surrounding the idyllic town of Rockford is one of the prettiest things to see in Illinois. Rockford also has plenty of family-friendly attractions including the Discovery Center Museum which has hundreds of interactive activities based on different topics from art and color to flight and electricity. There are also several dining options in Rockford and you can sample a range of delicious cuisines. 

Milwaukee, WI

Milwaukee is one of the cities you need to visit in the USA, and it’s easily reachable by Amtrack from Chicago. You can explore the historic Third Ward or Milwaukee Public Market, or go for a trek in Lakeshore State Park. The park is a 22-acre space right on the shoreline. It’s the perfect place to wander around during the summer months. If you’re looking for a city break from Chicago then Milwaukee could be ideal for you.

Grand Rapids, MI

Grand Rapids is famous for its breweries, so it’s great for beer connoisseurs. There are plenty of things to do in Grand Rapids that don’t involve beer as well. It’s also known for art and culture. You can check out the famous Grand Rapids Art Museum or Frederik Meijer’s Gardens and Sculpture. Chill out afterward and one of the many bars and restaurants. Grand Rapids offers a truly eclectic dining experience. 

Kankakee County, IL

Kankakee County is home to the River State Park which surrounds the river for approximately 11 miles. It’s great for hiking, fishing, and water sports. In the right season, you can also try your hand at foraging for mushrooms. The Chicago Bears also have one of their training grounds in Kankakee County at Olivet Nazarene University, so sports fans can check this out. You can find out more from the official tourism website. There are plenty of things to do and see and it’s only an hour’s drive from Chicago, making it ideal for a day trip or weekend stay.

*Post contributed by Jackie Sullivan, a peer travel writer born in the Midwest.*


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