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Chicago Day Trips: The Best Places for a Day-long Getaway

Chicago, also known as the “Windy City”, is a great place to live, but sometimes you just need a new perspective and a change of scenery. Luckily, the city’s central location in the Midwest means you have lots of options for fun Chicago day trips, so get out of town!

And you don’t even have to do the driving – travel by bus or train to many destinations around Chicago for a day or a weekend and relax as you head to your adventure. Made a last minute call to have a weekend getaway near Chicago and not sure where to start? No worries, we have some ideas for you!

Milwaukee, WI

To make the most of your Chicago day trip, head to Milwaukee! Just a little more than an hour away by bus or train, you’ll get to spend more time in the city – which is great because Milwaukee has so much to do that you might have trouble fitting it all in one day. Don’t miss the Milwaukee Art Museum, the signature attraction on the shores of Lake Michigan. And it might even be worth staying overnight just to say you closed the iconic dive bar Wolski’s Tavern. Find out about many more Milwaukee attractions here!

Lucas Peterson, Frugal Traveler columnist for The New York Times, used Wanderu to book a day trip from Chicago to Milwaukee and recounted his entire experience in the Wisconsin town from start to finish, covering awesome eateries and cool must-visit points of interest.

Check out Lucas’s article for more inspiration on places to check out in Milwaukee!

South Bend, IN

Sure, you know South Bend is the home of the Notre Dame Fighting Irish, but did you know it’s also a perfect destination for a fun day trip from Chicago? Explore along the river downtown – you can just go for a walk along the scenic waterway or go all out and kayak or raft down the river. If you have a sweet tooth, the South Bend Chocolate Cafe is pretty much your definition of heaven. And the Notre Dame campus is stunning and definitely worth a visit during your day in South Bend. Read more about all South Bend events and attractions here!

Grand Rapids, MI

Though it can be done in a day, if you have a little more time for a fun Chicago road trip, spend a weekend in Grand Rapids. If you love craft brews, you can’t pick a better place to sample what’s on tap than Beer City USA. Meijer Gardens combines a botanical garden and a sculpture garden into one beautiful destination. And you won’t run out of delicious things to eat in Grand Rapids, especially with a visit to all the local vendors at the Downtown Market. See what else makes Grand Rapids a great getaway here!

So don’t let lack of time or money stop you from getting away – book one of these cheap fun day trips from Chicago today on or by downloading the Wanderu app!

Which of these Midwestern cities would you most like to visit? Or do you have another Chicago day trip destination in mind? Share your favorites in the comments!

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About the author
Kate Sedrowski

Kate Sedrowski

Kate Sedrowski is on a mission to spread delight while inspiring and encouraging people to travel. Her favorite travel companion is her teddy bear, and her favorite souvenir is the scar from the broken nose she got in a snowball fight in Québec City.

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