If you live in Chicago you obviously have a long list of things to see and do at your doorstep, but it’s always fun to make an escape from the big city every once in a while. You don’t have to book a flight as there are some great road trips that can make for a fun weekend, week or even longer getaway. These are some of the best to embark on from the Windy City.


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Saugatuck, Michigan beach at Saugatuck Dunes State Park
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beach at Saugatuck Dunes State Park

Saugatuck, Michigan

Saugatuck is an especially picturesque small town filled with art galleries featuring local artists, mom-and-pop restaurants, unique shops and more, but the highlight is Saugatuck State Park. It features 14 miles of hiking trails that lead to 1,000 acres of rolling, wooded dunes that soar as high as 200 feet tall. It’s also home to two-and-a-half-miles of secluded beach along Lake Michigan, accessed via a just over the half-mile hike.

Lake Geneva, Wisconsin View of Lake Geneva in the fall Wisconsin
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View of Lake Geneva in the fall Wisconsin

Lake Geneva, Wisconsin

Lake Geneva is just 90 minutes away from Chicago, an ideal destination when you’re searching for a shorter road trip. Located on an eight-square-mile lake, you can look forward to walks on the 26-mile Geneva Lake Shore Path, an old Native American trail that extends the entire length of the shoreline with gorgeous views throughout, enjoy a romantic boat cruise or rent a boat for a memorable day on the water. away. In town you’ll find a wide range of dining, shopping and entertainment venues as well as spas for relaxing after a day of play.

Madison, Wisconsin skyline of Madison, Wisconsin
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skyline of Madison, Wisconsin

Madison, Wisconsin

The city of Madison is about a two-and-a-half-hour drive northwest of Chicago and offers plenty of family-friendly activities to enj0y. Crowds are fewer, and you’ll discover a fantastic culinary scene along with a wealth of cultural attractions like the Wisconsin Arboretum, the Chazen Museum of Art, the Madison Museum of Contemporary Art, and the Olbrich Botanical Gardens. Visit the local breweries, enjoy live music and shop the Dane County’s Farmers’ Market on Saturday mornings from April through November.

South Haven, Michigan Sunset at South Haven lighthouse Michigan
Sunset at South Haven lighthouse Michigan

South Haven, Michigan

While it may be a small port city, South Haven is only two hours from Chicago and it’s truly a haven, providing a tranquil beach retreat along Lake Michigan. The town itself is filled with restaurants and unique shops, and also hosts the Michigan Maritime Museum and a world-renowned lighthouse that’s served as a guiding light to ships entering the Black River for well over a century.  The beautiful sandy beach is the highlight here, a place where many come to soak up the sunshine and enjoy all sorts of water sports.

Milwaukee, Wisconsin River Walk in Milwaukee
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River Walk in Milwaukee

Milwaukee, Wisconsin

Just two hours north of Chicago, Milwaukee offers lots of fun attractions without the big tourist crowds. It is a hot spot for gourmet dining experiences, theater, art museums and much more. Of course, it’s famous for its beer, with 15 different brewery tour options, so beer enthusiasts will have plenty to choose from. It’s free to visit the Haggerty Museum of Art with its classic and contemporary works, while Black Cat Alley hosts 30,000-square-feet of outdoor space dedicated to local artists’ murals and street art. If you want to get active, consider paddling right through downtown to work off all that beer and delicious food. You can rent a kayak, or bring your own, and paddle down the Milwaukee River.

Starved Rock State Park, Utica, Illinois Waterfall at Starved Rock State Park
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Waterfall at Starved Rock State Park

Starved Rock State Park, Utica, Illinois

Starved Rock State Park is just 100 miles southwest of Chicago, offering an ideal spot to enjoy nature with more than a dozen sandstone canyons along with beautiful waterfalls that are especially powerful in the spring and after heavy rainfall – this is also the perfect time for viewing colorful wildflowers. No matter what the season is, hiking is fabulous here – walk through the tranquil forest, keeping an eye out for deer and birds, including bald eagles, along the way. If you visit during the fall, it’s filled with vibrant foliage, and in winter you can even go ice climbing.

Galena, Illinois Shops along Main Street, Galena
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Shops along Main Street, Galena

Galena, Illinois

A three-hour drive will bring you to Galena, named as one of TripAdvisor’s “Top 10 Charming Small Towns.” Look forward to strolling cobbled streets lined with historic mansions as well as all sorts of outdoor adventure nearby.  Take a rafting trip, hike the bluffs that overlook the Mississippi River, and during the chillier months of the year, hit the slopes at the nearby ski resort.

Mackinac Island, Michigan Mackinac Island, Michigan
Mackinac Island, Michigan

Mackinac Island, Michigan

Mackinac Island is ideal if you’re looking for a long road trip that will get you away from it all, and it’s well worth the drive. Plan for a little over six hours plus the half-hour ferry ride to discover this island tucked between the northern tip of Michigan and the Upper Peninsula. Especially peaceful, the island is car-free with transport by horse-drawn carriage and bicycle.  Hike the network of 71 miles of trails that wind through the woods and limestone outcroppings, or ride a bike on the scenic coastline while listening to the sounds of nature and taking in the spectacular sights.

Door County, Wisconsin Cave Point, Door County
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Cave Point, Door County

Door County, Wisconsin

Just under 250 miles north of Chicago, sandwiched between Lake Michigan and Green Bay, Door County is famous for its family-friendly attractions and 300 miles of gorgeous shoreline. The “Cape Cod of the Midwest,” as it’s sometimes referred too, offers a wide range of water sports, including kayaking and paddle boarding, along with opportunities for hiking and visiting multiple lighthouses. Climb the 100 steps to the top of Cana Island Lighthouse in Bailey’s Harbor for an especially picturesque view from above. As you walk along the rock-ledge shore, you can capture some postcard-perfect photos he 1870s lighthouse.  Throughout the peninsula, there are countless state parks, charming small towns and roadside cherry stands to take advantage of. Bailey’s Harbor is a must for wine enthusiasts, home to Stone’s Throw Winery which offers tastings and occasional live entertainment.

Carbondale, Illinois Giant City State Park near Carbondale, Illinois
Giant City State Park near Carbondale, Illinois

Carbondale, Illinois

It’s a 5.5-hour drive southwest to Carbondale, a college town that offers lots to do, including enjoying refreshing drinks at places like Hangar 9 and The Cellar, as well as dining on a mouthwatering meal at nearby 17th Street BBQ in Murphysboro, renowned for serving the very best in the state. The southern end of the city opens up to the Shawnee National Forest, home to many wineries as the start of the Shawnee Hills Wine Trail which features a dozen vineyards in picturesque settings, for wine tasting and dining. There are 14 parks in the area for exploring nature and enjoying active pursuits as well.

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