The 5 Best Day Trips From Chicago

Get out of Chicago and watch a game at the University of Michigan
Get out of Chicago and watch a game at the University of Michigan | © Chris Rabior Sports Photography / Alamy Stock Photo
Photo of Molly Sprayregen
22 May 2019

Even if you love city life, it can be nice to take a break from the commotion every once in a while. Chicago is well-positioned for a number of amazing day trips, whether you are looking to be active in the outdoors, relax and sip delicious craft beer, explore small-town shops, or some combination of it all. Here are the five best day trips from Chicago.

Visit Starved Rock State Park

Trail into Tonti Canyon in Starved Rock State Park in Illinois | © wildnerdpix / Alamy Stock Photo

Starved Rock is one of the most popular day trips from Chicago and is an ideal place to visit if you are looking to immerse yourself in quintessential Midwestern nature. It takes less than two hours to drive to this beautiful park filled with canyons and waterfalls, which visitors can hike to year-round.

In the warmer months, there are also activities like kayaking, canoeing and horseback riding. In the winter, visitors can see the frozen waterfalls and partake in ice climbing and cross-country skiing. If you want to turn this into more than a day trip, there is also a campground where you can spend the night roasting marshmallows and sleeping under the stars.

Take a bike ride to 3 Floyds Brewpub

Cycling along the lakefront in Chicago | © D Guest Smith / Alamy Stock Photo

This day trip allows you to enjoy so many things at once: a lovely bike ride, sprawling views of Lake Michigan and delicious food and drink from a famous pub. In 2018, the Brewer’s Association named 3 Floyds, located in Munster, Indiana, one of the top 50 brewing companies by sales volume.

While you can drive here for a visit, one of the most fun ways to get here is by bike. The ride is about 34 miles (55 kilometers) and, depending on speed, takes between two-and-a-half and three hours. You’ll spend a large portion of the journey along Chicago’s gorgeous lakefront path. When you arrive, celebrate your hard work with one of 3 Floyds’ famous brews as well as a delicious burger – and maybe some cheese curds on the side. You deserve it after all that work. When you’ve filled up, there is a Metra train station about 10mi (16km) away, so you don’t have to ride back to the city.

Relax in Saugatuck, Michigan

A lake in Saugatuck, Michigan. | © Jerome Flynn / Alamy Stock Photo

Saugatuck is a delightful little lakeside town. Just a two-and-a-half-hour drive from the city, it’s a wonderful place to shop, eat and lounge. During the summer, you can visit Saugatuck’s Farmers Market on Fridays. If you have time, you can also check out the other neighboring and equally cute towns of Holland and Douglas. If none of these strike your fancy, you can explore one of Illinois’s own charming, small towns.

Tour breweries in Milwaukee, Wisconsin

Miller Brewing Company in Milwaukee, Wisconsin. | © Bruce Leighty / Alamy Stock Photo

It takes about one hour and 40 minutes to drive from Chicago to Milwaukee, a city known for its centuries of rich brewing history. Milwaukee is currently home to dozens of brewers, large and small, including the Pabst Milwaukee Brewery, Miller Brewing Company, Good City Brewing and Black Husky Brewing.

Watch a Big 10 football game

University of Michigan Wolverines football game, Ann Arbor, Michigan. | © Lloyd Sutton / Alamy Stock Photo

Chicago is between two and four hours from the famed college towns of Ann Arbor, Michigan; Madison, Wisconsin; Iowa City, Iowa; and Champaign-Urbana, Illinois. Homes to the University of Michigan, the University of Wisconsin, the University of Iowa and the University of Illinois respectively, these locales are brimming with shops, restaurants and school spirit and are fun to explore on any day. For the ultimate Big 10 experience, though, visit one of these institutions for a football game. Spend the day tailgating and soaking up the energy and excitement of the student body before settling into the stadium to cheer on the home team.

This article is an updated version of a story created by Elizabeth Newhart.

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