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With its millions of things to see and do, Chicago is one of America’s greatest cities to visit. But if you’re not taking side trips outside of the city, you’re missing out. You see, the Windy City is surrounded by a bunch of fun spots that offer a totally different Midwestern perspective—and they’re super close and deserving of a day trip or even a weekender. Here are our six of our faves.

RELATED: Three perfect days in Chicago


Photo courtesy of the Great Wolf Lodge

Wisconsin Dells

This is a must-do if you’ve got kids (or if you’re an adult who loves waterparks). It’s just 3 hours outside of Chicago, and the entirety of this resort community surrounds major waterpark hotels. It’s basically the waterpark capital of the world. What makes it even better is that the majority of the parks are indoors, so you can come here in the middle of a Chicago winter, and spend the entire time in a bathing suit. Our favorite spot is the Great Wolf Lodge Wisconsin Dells, but the Kalahari and the Wilderness are also amazing.
Distance from Chicago: 191 miles


Trover photo by Meghan Hernandez

Starved Rock

It’s the reason that Chicagoans don’t necessarily need to pack their bags and fly to Colorado. This day trip to Oglesby provides waterfalls, trails, fishing and the most amazing views. Did we mention that it’s totally gratis? If you’re feeling extra outdoorsy, stay in a cabin inside the park—or you can spend the night just a mile away at Grizzly Jack’s Grand Bear Resort.
Distance from Chicago: 90 miles


Trover photo by Honoka


Get out of Chicago for a day or a weekend, and check out Wisconsin, which is just an hour away. Binge on cheese, beer and motorcycles (the Harley-Davidson Museum contains one of Elvis Presley’s babies). Take a stroll along the Riverwalk, wander through the Milwaukee Art Museum and nibble your way through the Milwaukee Public Market. There are so many great hotels in downtown Milwaukee, but we keep returning to The Pfister Hotel.
Distance from Chicago: 90 miles

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Trover photo by Michelle M


History buffs should take a few days to check out Abraham Lincoln’s home, along with all the governmental workings of the state. Learn more about Lincoln via the Presidential Library and Museum, tour his restored home and check out the Lincoln Tomb in Oak Ridge Cemetery. The Route 66 Car Museum, Mother’s Brewing Company and the Fantastic Caverns are also popular. Staying at the Wyndham Springfield City Centre keeps you close to the action.
Distance from Chicago: 200 miles


Trover photo by Gizmo Goes West

Indiana Dunes

Take a day or two to relax where Chicagoans like to go when they have some time to chill. There are sandy beaches lacking big Chicago crowds, as well as dunes, marshlands, forests and tons of places to escape if you don’t want to see anyone. It should be ranked on lists of the most beautiful places on earth, but we’re not complaining: We like it untouched, just the way it is. It’s an easy day trip from Chicago, but if you want to stay overnight, we recommend Blue Jay Manor.
Distance from Chicago: 50 miles

Old building on a street of Galena, Illinois


This is the quaintest little town ever. It’ll remind you of Small Town, USA, complete with an old-fashioned ice-cream parlor, an old blacksmith shop (now a museum) and antique malls galore. Many people like to travel here to ski, to play golf and go horseback riding—and the spas are also infamous. It’s basically where Chicagoans go to have a weekend of luxury. Stay at Eagle Ridge Resort & Spa to truly get pampered in every way.


Tagged: Chicago, Chicago, Midwest

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Danielle Braff

Danielle Braff

Danielle lives in Chicago with her family, two cats and a dog, but she's constantly researching her next vacation. Check out her other articles at

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