Chicago is a vacation destination all on its own. After all, more than 50 million people flock to the Windy City every year to experience its amazing culture, shopping and restaurants. But even the most loyal Chicagoans need to escape the hustle of the city from time to time. There are many cities nearby that offer exciting and adventurous experiences. Here is a list of some of the most unforgettable weekend getaways from Chicago.

  1. Milwaukee, Wisconsin

    Milwaukee has a lot to offer, but the Harley-Davidson Museum is a must-visit for bike riders. Written descriptions of the motorcycle displays are available. You can use an audio headset for an extra fee.

  2. Three Oaks, Michigan

    Support the local farmers by shopping at the Three Oaks Farmers Market. You can buy plants, fresh flowers and farm-produced natural foods.

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  3. Galena, Illinois

    Many visitors to Galena stop by the 40-year-old Galena Cellars winery. Here, you can sample some of the finest wines with cheese or chocolate pairings. Discover how wines are processed, and tour the cellar and barrel rooms.

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  4. Starved Rock State Park, Illinois

    Walk through this peaceful state park, and keep an eye out for deer, squirrels and bald eagles. Visit in springtime to see the beauty of the waterfalls and canyons. Admire the wildflowers that bloom all year round, or spot seasonal blossoms depending on the time of year.

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  5. Saugatuck, Michigan

    Take a memorable ride through the dunes in Saugatuck, and keep a sharp eye out for wildlife. The 40-minute adventure requires your signature on a waiver, so you know it’s exciting. It’s a good idea to make sure the tour is available before you visit.

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  6. Lake Geneva, Wisconsin

    Lake Geneva is a resort town 80 miles from Chicago. Visitors enjoy the resorts, vacation rentals, restaurants and beaches.

  7. Iowa City, Iowa

    Visit Lake Macbride State Park for some exciting water activities. Rent a boat and go fishing, swim in the designated area on the beach, and go camping with your loved ones.

  8. Ann Arbor, Michigan

    Bring your favorite camera and practice your photography skills in Ann Arbor. Head to East Liberty Street and take photos of the unique graffiti art on the walls.

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  9. Bloomington, Indiana

    Visit Monroe Lake for a fishing adventure. Spend the day enjoying the views of the protected forests, or try water skiing on the lake.

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  10. Louisville, Kentucky

    Kentucky, usa, america. Picture by <a href="" target="_blank">USA-Reiseblogger</a> on <a href="" target="_blank">Pixabay</a>.
    Kentucky, usa, america. Picture by USA-Reiseblogger on Pixabay.

    The Louisville Zoo is a popular destination, with over 1,500 animals like tigers, bears and camels. You might also enjoy visiting the Copper and Kings American Brandy Company, where you can tour the distillery and taste the brandy.

  11. Starved Rock State Park

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    Starved Rock State Park is 90 miles from Chicago, and it delivers a classic outdoor experience. Follow trails through the woods and take pictures with stunning waterfalls in the background. Rent kayaks and explore the park from the water for an experience that combines a great workout with unmatched scenery. There are also several wineries in the area around Starved Rock State Park where wine tastings and tours are offered.

  12. Indiana Dunes State Park

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    When you’re searching for weekend getaways near Chicago, consider Indiana Dunes State Park. This park is a 54-mile drive from Chicago, so it takes just under an hour to get there. Pack your binoculars to go birding, or ride bikes on the trails that wind through the park. The pristine beaches in the park also offer opportunities to stretch out on the sand for sunbathing.

  13. Michigan City, Indiana

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    Travel 60 miles out of the city to spend the weekend in Michigan City, Indiana to see some tourist attractions and learn about local history while relaxing. This trip provides the business of the city while still offering guests a small-town experience. Stroll on the beach or check out the historic lighthouse and pier. Or, visit the zoo and climb the observation tower to get a bird’s eye view of the area.

  14. Nappanee, Indiana

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    Enjoy one of Nappanee’s summer festivals, like the Apple Festival. Catch a glimpse of members of the Amish community, or visit the Amish restaurant, Das Dutchman Essenhaus to sample classic Amish food. Check the calendar to see if the Shipshewana Flea Market is open when you’re visiting Nappanee for some eclectic antique shopping.

  15. Devil’s Lake State Park

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    Devil’s Lake is a bit farther from Chicago than the other trips, and it’s actually across state lines into Wisconsin. Devil’s Lake is the biggest state park in Wisconsin, and it’s home to some unique rock formations. Be sure to pack a camera to capture memorable images of your trip to this stunning, natural setting.

  16. Mackinac Island

    Step back in time at Mackinac Island. A fast ferry gets you there and then there’s no more motorized transportation. Visitors either walk, bike or take horse-drawn carriages. The island is picturesque with the cold, blue water of Lake Huron and the Round Island Lighthouse in view from most locations. The island consists of centuries-old buildings, a few restaurants, bars and shops. Vacation rental homes are available throughout the island, and some are located right on the water’s edge.

  17. Cedar Rapids, Iowa

    Venture over to Cedar Rapids and enjoy vineyard touring and wine tasting at Tabor Home Vineyards. If you’re a museum buff, you’ll enjoy the cultural aspects of Cedar Rapids. Tour the African American Museum, the Cedar Rapids Museum of Art or the Carl and Mary Koehler History Center. Take a look at the National Motorcycle Museum that houses 230 motorcycles from yesteryear. After touring, indulge in coffee and pastries at The Blue Strawberry Company.

  18. Geneva, Illinois

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    Just about one hour’s drive from the city, this cool riverside town is an oasis known for its outdoor restaurants, historic downtown shopping district with more than 150 shops and eateries, amazing architecture and fabulous outdoor recreation. For example, Island Park is located right on Fox River, and it’s packed with things to do, including the Fox River Bike Trail, a playground with a tree house and gorgeous gardens.

  19. Madison, Wisconsin

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    It’s about 147 miles from Chicago, but the drive is worth it, especially if you bring your appetite with you. This Midwestern foodie destination boasts more than 600 restaurants, so you’re sure to find exciting culinary adventures. Madison also offers a great art scene with plenty of museums, galleries and shops to choose from. The Bolz Conservatory at Olbrich Botanical Gardens is one of the most popular year-round attractions with its gorgeous plants, flowers and soaring glass pyramid.

  20. Amish Country, Indiana


    Located about 110 miles away, Indiana’s Amish Country is one of the best weekend trips from Chicago for anyone who feels like escaping to the country. Listen to the soothing sounds of horse hooves while you watch the Amish buggies drive by. Also, the region is home to an astounding variety of attractions ranging from artisan studios to quilt gardens to riverfront dining. Of course, a drive on Heritage Trail is a must before you pack up your vacation rental and head home.

Ready to escape the city life for a while? Book a beautiful rental on VacationRenter now!