The Best Road Trips from Chicago with Itineraries

Looking to get out and explore? There are so many unique places to visit that are just a car ride away! From quaint small towns to interesting cities to exciting outdoor adventure and everything in between, here are the best road trips from Chicago.

Afterward, you may also be interested in reading suggestions for

Fun Spring Break Trips from Chicago.

The Best Road Trips from Chicago

Starting with quick weekend getaways, this list is ordered by distance and ends with long road trips from Chicago.

One of the most beautiful Midwest states is just a short drive from Chicago, here are fun day trips in Michigan to help you plan. 

I hope you enjoyed my favorite road trips from Chicago 2021 edition! If you have any other recommendations, please let us know in the comments below!

The top picture is a sweeping view of a valley filled with trees with fall color in Porcupine Mountains Wilderness State Park and the bottom is a lake in Illinois with cypress trees that have orange and green leaves with a text overlay that says the best road trips from Chicago.

A hiking trail in Shawnee National Forest lined with green ferns and bushes and large rock outcropping.

A picture of a hiking trail in Turkey Run State Park with green moss covering a rock outcropping and a text that says, the best getaways from Chicago.

Sunset with a lighthouse.

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