Road Trip Destinations From Chicago

The weather is changing, so you know what that means! It’s time to schedule a self-care weekend to rest and recharge.

To some that may look like spending a weekend alone at home or reading their favorite book while snuggled under a comfy blanket. For others though getting out of town is their definition of a break. There’s nothing like exploring a new place especially as the fall season begins.

If you are looking to take a weekend trip or day trip there are plenty of road trip locations that are easily accessible from Chicago. Here are 3 road trip destinations from Chicago that you can start planning now!

Milwaukee, WI

Milwaukee, WI
via milwaukeemag

Milwaukee is the perfect day trip for those that are looking to explore a metropolitan area, but escape the big city feel of Chicago. This city is full of charm and you are sure to find an activity you’ll love no matter what time of the year you visit!

While Milwaukee is just an hour and a half drive from Chicago many prefer to catch an Amtrak train, which stops right in the heart of the city. To start your day there are plenty of trendy breakfast and brunch spots to choose from. You’re sure to find something you love.

Visitors can enjoy exploring the Harley Davidson Museum, Milwaukee Art Museum, Milwaukee County Zoo and other attractions. If you are a nature lover there’s plenty of trails to walk and places to hike that are beautiful year round.

Road trip to Fennville, MI

Fennville, MI
via tripadvisor

Who doesn’t love a relaxing getaway? Fennville, Michigan is a quiet county that is located roughly 2 hours northeast of Chicago.

Tourists often come here for its beautiful nature-related sights. There is no shortage of outdoor activities to participate in during your visit. You can enjoy a stroll in Westside County Park or visit the beach at Pier Cove Park to relax by the water. Once you’re ready for a change of scenery you can head over to Fenn Valley Vineyards to enjoy a wine tasting with a group or privately.

If you plan to eat at a local restaurant reservations I recommend that you make a reservation. Also, make sure to carry your mask.

Road trip to Oglesby, IL

Starved Rock State Park
via timeout

Oglesby, IL is home to the beautiful award winning Starved Rock State Park, known for its hiking trails and seasonal waterfalls. Visitors can enjoy over 13 miles of trails, fishing (ice fishing, too) and boating in the Illinois River as well as breathtaking views and great places to relax.

This trip is a great educational opportunity, due to the history etched in this state park. In the 1760s, Chief Pontiac of the Ottawa tribe attended a council meeting that turned violent. Chief Pontiac was stabbed by an Illinois-Peoria Brave, which ultimately caused vengeance to arise within Pontiac’s followers. A long battle broke out and the Illinois took refuge on top of the great rock. After several days, the remaining Illinois began to die of starvation, which gave this historic park its name – Starved Rock.

If you are planning a trip here please remember to bring a mask. While it’s not a requirement to wear a mask when hiking I recommend that you bring one, so that when you interact with people you are protected.

There are plenty of other great weekend road trips to take from Chicago, but I wanted to highlight some of my favorites. To ensure you maximize your experience I encourage you to build your travel itinerary beforehand.

For more travel tips check out my post on Traveling On A Budget.