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14 Best Road Trips From Chicago, Illinois (2024 Guide)

14 Best Road Trips From Chicago, Illinois (2024 Guide)

Check out our list of the best road trips from Chicago, Illinois to discover more of the United States Midwest!

Chicago, the famous “Windy City” is one of the USA’s most incredible cities. There is a wealth of experiences awaiting travellers in Chicago, from engaging in the sports scene to tasting local food delicacies or diving into the art and history.

But beyond the city limits of the downtown area, there is much more to see and do. For those who have time on their hands, try one of these road trips from Chicago!

Whether you’re looking for quick day trips or a more ambitious weekend road trip, a scenic drive outside Chicago can open your eyes to the wonders of the Midwest.

Visit Milwaukee or Cleveland for the big city vibes, or seek out small town charm in rural Illinois. Take on a convenient road trip to somewhere nearby on the shores of Lake Michigan, or embark on long weekend road trips into neighboring states.

Check out glorious state parks such as Starved Rock State Park, or seek out world-class museums in another Midwest city like St. Louis. Road trips from Chicago are an amazing way to expand your horizons while visiting this iconic US city.

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14 Best Road Trips From Chicago

These road trips from Chicago showcase all the highlights of the area, whether you’re seeking a resort town on a lake, a busy city with street art and nightlife, or a remote state forest.

City dwellers hoping to venture outside Chicago and check out more of the Midwest have so many options for road trips, so consider one of these destinations for your next getaway!

1. Starved Rock State Park

  • Distance from Chicago: 93 miles
  • Driving time: 1.5 hours

At just over an hour and half from the Windy City, Starved Rock State Park makes an excellent road trip for nature lovers.

As you drive southwest, the urban skyline of Chicago gradually fades into rolling farmlands, dotted with charming barns and wind turbines. You might stop in towns like Ottawa or Utica, where cozy diners and antique shops showcase the relaxed pace of rural Illinois.

Starved Rock State Park is one of the best state parks in Illinois, famous for its sandstone canyons and seasonal waterfalls.

With over 13 miles of hiking trails, visitors can explore diverse ecosystems, from riverfront views along the Illinois River to forested paths winding through canyon walls. In winter you can even go cross country skiing here!

Starved Rock State Park is also…

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