6 Family Road Trips to Take From Chicago This Summer

Looking for some adventure this summer that will bring your family closer together and create lasting memories? Consider the good old family road trip. Despite the gas station meals, sibling arguments, bathroom breaks, and wrong turns, we promise these road trips are worth the trek. These destinations are 10 hours or less from the Chicago area so the drive can be done in a day if you are adventurous, and we’ve even suggested great places to explore during a much-needed pit stop. 

Destination: Sandusky, Ohio

Drive Time: 6 hours

Pit Stop: Toledo, Ohio


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Take a true Griswold family-style road trip to Cedar Point, the second-oldest operating amusement park in the country (just make sure you check the calendar for potential closings — remember this iconic scene?). Located on Lake Erie in Sandusky, Ohio, the city considered to be the roller coaster capital of the world, Cedar Point also includes a waterpark, a petting zoo, a mile-long beach with jet skiing and kayaking, and is surrounded by hotels and even campgrounds. We suggest planning at least three days to enjoy all Cedar Point has to offer and staying close to the park for convenience (and to save on parking!).

Destination: Toronto, Canada

Drive Time: 10 hours

Pit Stop: Detroit, Michigan


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Grab your passports (and the kids’ birth certificates) for this epic family road trip to Toronto, Canada. Toronto is a beautiful city to visit in the summer, with parks, museums, beaches, and more. We suggest renting a house on Airbnb (The Beaches is a cute family-friendly area) and using Toronto’s streetcar system to explore. Amsterdam Brewery is a great place for lunch or dinner, with view of the Toronto harbor and a large menu that will please even the pickiest eaters. You can’t miss the Roundhouse Park right under the CN Tower, home to the Toronto Railway Museum and Steam Whistle Brewing.

Destination: Door County, Wisconsin

Drive Time: 4 hours

Pit Stop: Sheboygan, Wisconsin


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If you’ve been to Door County, Wisconsin, you know the place is magical. Located on a peninsula between Green Bay and Lake Michigan, Door County is full of cute villages, parks, beaches, water activities, and the arts. If you book well enough in advance, camping in Peninsula State Park is an incredible experience. For shopping, check out Sister Bay, and while you’re there you have to take the kids to see the goats who live on the grass roof of Al Johnson’s. For dinner, an iconic meal is a fish fry (offered all over the county, but Pelletier’s in Fish Creek is a favorite) and you can’t miss ice cream at the historic Wilson’s in Ephraim either. Save a day for a trip to Washington Island via the ferry, where you can spend an afternoon hiking and hanging at the beach.

Destination: Minneapolis, Minnesota

Drive Time: 6 hours

Pit Stop: Madison, Wisconsin


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Minneapolis, the “city by nature,” is full of family fun in the summer and is a great city to explore by bike, water, or foot. Bring your bikes or rent to take advantage of the bike trails around downtown and the surrounding unique neighborhoods. You can’t miss a Juicy Lucy burger at the 5-8 Club and the family needs to take a selfie in front of the iconic cherry sculpture at the Walker Art Center. Take in a Twins baseball game or if you are feeling adventurous, visit the Mall of America, the country’s biggest mall in Bloomington, a suburb of Minneapolis. Yes, they have every store imaginable, but they also have a fun entertainment complex that includes a theme park with coasters and rides in the middle of the mall and an aquarium. 

Destination: Traverse City, Michigan

Drive Time: 6 hours

Pit stop: Grand Rapids, Michigan


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The second largest city in Michigan, Traverse City sits on Lake Michigan and is known for producing tart cherries, wine, and for their love of the outdoors. Pyramid Point-Sleeping Bear Dunes is a popular outdoor spot for hiking and Bryant Park is a family-friendly beach to spend a day at. The area is known for its treasure hunting, so make sure the kids keep their eyes peeled while playing in the sand. Check out the historic downtown for local shopping and stop by North Peak Brewing Company, a brew pub and restaurant, located in a former candy factory (emphasize the “former” when telling the kids). For lodging, book one of the many waterfront cabins and homes to retreat to for a fun alternative to a hotel stay.

Destination: Bowling Green, Kentucky

Drive Time: 7 hours

Pit Stop: Indianapolis, Indiana


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Head south to Bowling Green, Kentucky, for an adventure underground that the kids will love! With Bowling Green as your home base, you can travel to the Mammoth Cave National Park to explore the world’s longest cave system, complete with bats and waterfalls. Lost River Caves in Bowling Green, is one of the only caves to allow visitors to experience the natural underground wonders by boat (warning: not for those with claustrophobia). Another local destination is the National Corvette Museum, where the main attraction might just be the giant sinkhole that swallowed eight valuable cars in 2014. After a full day of exploring, White Squirrel Brewery is a family-friendly place to eat and unwind.

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