The 5 Best Day Trips From Chicago

May, 20, 2022

As the third biggest city in the United States, Chicago already has more than enough to do. This stunning city is filled with magnificent architecture, incredible food, a surprisingly large amount of beaches, and some of the nicest people you’ll meet in the United States. Still, if you spend enough time in one place, you might start to consider looking elsewhere to get a breath of fresh air. If you are looking for the best day trips from Chicago, this post is for you!

1. Milwaukee, Wisconsin

Milwaukee isn’t the capital of Wisconsin, but it is the biggest city by a wide margin. Many people would also tell you it is the best. In many ways, Milwaukee is like the younger sibling of Chicago, as both are big, beautiful cities along Lake Michigan, but Milwaukee tends to live in Chicago’s shadow due to Chicago’s sheer size. Still, located just an hour and a half north of Chicago, Milwaukee is easily the best day trip from The Windy City. From delicious cheese to countless craft breweries, this city is sure to leave you with a full stomach.

To get there, you can either drive or take a train! If you plan on hitting a couple of the famous breweries (Miller is from here!), I recommend just taking a train north from Chicago’s Union Station. It takes the same amount of time, is very affordable, and gets rid of your need to drive home.

2. Madison, Wisconsin

While smaller than Milwaukee, Madison is the capital of Wisconsin and is known as one of the most beautiful cities in the Midwest. Shockingly, it has also been at or near the top of the list of the American cities with the highest quality of life for several years in a row. The University of Wisconsin is located here, and the whole city breathes Wisconsin football.

As both a major college town and a capital city, you get the best of both worlds; refined, nice neighborhoods along with great restaurants, bars, cafes and activities to appeal to the university crowd. Madison is located about two and a half hours north of Chicago, making this one a bit further of a day trip but still absolutely worth the time and effort. As Madison is situated on an isthmus between two lakes, this is one of very few places where you can catch both the sunrise and sunset over the water.

3. Grand Rapids, Michigan

First things first, I need to start by pointing out that this is the furthest day trip on this list. Grand Rapids is a full three hours east of Chicago, ruling this day trip out for most people. It is so cool, though, that I felt the need to include it anyway. Grand Rapids is located in Western Michigan, right by Lake Michigan, and it is one of the coolest, old-style places you’ll visit on a day trip from Chicago. This little city is filled to the brim with farm-to-table restaurants, fantastic local breweries, and art galore.

From a sculpture park to many great art galleries, this little under-heralded city is an art enthusiast’s dream. Additionally, as Michigan is one of the most agriculturally diverse states in the entire country, the farm-to-table restaurants are literally everywhere and always serve up the freshest, tastiest foods. If you’re looking for an excuse to go to Michigan while you’re in Chicago, look no further.

4. South Bend, Indiana

South Bend, Indiana itself doesn’t have too much going on, other than the fact that it is home to the University of Notre Dame. As one of the oldest Catholic universities in the United States and a major college football contender most years, the University of Notre Dame is a special place that is absolutely worth a visit. The campus is beautiful, and it is located just an hour and a half east of Chicago by car or train.

This school has been a symbol of Catholicism in the United States for over a century and a half, and it has produced some globally-known alumni, ranging from scientists, to businessmen, to Supreme Court Justices. While I haven’t visited every university in the United States (who has?), I have visited a lot of beautiful ones, and Notre Dame’s campus probably cracks my top five. If you have the time, I definitely recommend checking it out!

5. Holland, Michigan

Holland, Michigan is one of the most unique places you can visit on a day trip from Chicago, and it is this uniqueness that earned it a spot on this list. This little town was founded by Dutch settlers in the mid-1800s as they escaped religious persecution in the Netherlands. To this day, you still feel like you are walking through the Netherlands, as the architecture and the beautiful flowers transport you across the Atlantic.

From the beautiful tulips, to the scrumptious breakfasts, to the delicious beers, to the picturesque windmill park, this little Dutch city is the perfect place for a day trip. it is also small enough to where you really feel like you’ve seen it all at the end of the day. Holland, Michigan is located two and a half hours from Chicago, and it is absolutely worth checking out.

That rounds out my list of the 5 best day trips from Chicago! Do you see yourself going on any of these awesome getaways any time soon? Drop a comment below!


Hi! I’m Greg, a Pittsburgh-based dad who juggles a 9-5 with a passion for traveling the world. I've spent time living in Mexico, Italy, and China, have traveled to nearly 50 countries, and make a habit of scratching epic experiences off of my bucket list.

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Meet The Family!

We're a family who seeks adventure both in our backyard and also around the world. We've spent time living in Mexico, Italy, and China, have traveled to nearly 50 countries. Life is short! All we have is this present moment to fulfill the dreams God has given us.