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10 Road Trips From Chicago That Make Leaving The City Worth It

TheTravel logo TheTravel 7/15/2022 Dominic Horner
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Chicago is undeniably one of the best cities to live in America. Even with the city’s convenience, sometimes Chicago feels like a bunch of blocks with no thrill. Summer is the best time to explore the thrill, and moving out of Chicago seems to be the real deal.

Driving away from the chaotic and normal life of the city is an underrated experience that vacationers need to explore more often.

Here are 10 road trips from Chicago worth the effort.

Cincinnati, Ohio

In the recent past, the state of Ohio continues to tick all the right boxes in tourism matters. This time around, it is the city of Cincinnati serving some deserved justice to the state. From its natural resources to the beautiful skyline, the thrill in this city is virtually endless. The Ohio River is a tantalizing beauty that vacationers will truly love.

  • Driving Time: Five hours

Related: This Is The Best Month To Visit Chicago & Why You’ll Want To Go

Galena, Illinois

The beauty of a road trip doesn't solely depend on the distance traveled. The experience matters too. With Galena, it is more about the experience than the traveling time. It is among the most historical cities in modern-day America. The city has stuck with architectural designs from the early 19th century. The city has lived to the billing of one of America’s most conservative regions. Also, the delicacies served in this part of Illinois are worth the drive.

  • Drive Time: Five hours

Related: Chicago, Illinois: Planning The Perfect Weekend

Starved Rock State Park, Illinois

The Starved Rock State Park is the best way to experience Illinois' wild side. In fact, this park is worlds apart from anything else in Illinois. From the beautiful vegetation covering the area to the free-flowing waterfalls in the park, vacationers are rewarded greatly for their courage to drive out of Chicago. While at the park, vacationers have multiple activities to explore including hiking and biking. During the warmers months, adventures will have a good time soaking in the waterfall before they dry up.

  • Drive Time: One hour 30 minutes

Bloomington, Illinois

What is it about college towns that vacationers want to spend more time in those areas yet the population is so high? Well, college towns have a special kind of vibe since they are dominated by youthful individuals. With Bloomington, vacationers have more than just the young people vibe. It is also a great interaction with nature. Surrounded by thick forests and lakes, this neighborhood gifts tourists a lot to explore. Going out fishing in any of the reservoir lakes in the region and bringing the catch back to Chicago is part of the experience that creates a lasting memory.

  • Drive Time: Four hours

McHenry County, Illinois

McHenry is another perfect escape route from Chicago. It is the place to be for individuals who like visiting parks. But who doesn’t anyway? These parks provide the perfect places for vacationers to interact with nature. Apart from the park, it is the best place to understand what buying local build local means. To them, it is local products first and the rest come second. Enjoy some of the most authentic frozen custard in any of the county's dairy farms.

  • Driving Time: One hour 30 minutes

Lake Geneva, Wisconsin

What is the best description of the ultimate Chicago road trip? Whether long or short, the quality of a specific road trip boils down to the activities available for the vacationers to explore. The Legendary Lake Geneva needs no introduction as its general appeal speaks volumes. This lake forms a reasonable escape route with multiple activities for vacationers to explore.

  • Drive Time: One hour 30 minutes

Springfield, Illinois

Road trips are not a preserve for nature enthusiasts alone. Historians as well have an equal opportunity and that’s what Springfield is all about. One of America’s liberators in President Abraham Lincoln has its roots in this town. One of the must-do activities for vacationers in Chicago is visiting his tomb at the Oak Ridge Cemetery is a great way to connect with American history.

  • Drive Time: Three hours

Louisville, Kentucky

Louisville is by far the largest city in Kentucky and a great place to visit. Vacationers seeking an escape route away from Chicago find this city to be a great choice. From its incredible shoreline to the multiple distilleries to be explored, this city is indeed a must-visit for road trip enthusiasts.

  • Drive Time: Five hours

Mammoth Cave National Park, Kentucky

Once again, it is mighty Kentucky doing the magic for Chicago vacationers. It is the world’s largest cave system with more than 400 miles of underground pathways. Also, it is one of the longest road trips away from Chicago. With six hours of driving, this trip would be best pursued for a weekend.

  • Drive Time: Six hours

South Haven, Michigan

Vacationers driving out of Chicago in search of a better thrill find a good one in South Haven. It is a small port city in Michigan barely two hours away. This city is a bit laid back compared to Chicago’s chaotic nature. From exotic restaurants to relaxed beaches, South Haven automatically becomes the perfect escape route away from Chicago.

  • Driving Time: Two hours
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