Weekend getaways from Chicago can be found in just about every direction from the city. Plan a few trips to try several different options. Look for vacation rental homes that give you all the creature comforts you need while traveling.

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Here’s where you can go for a weekend near Chicago

  1. Saugatuck, Michigan

    Saugatuck is a quaint town overflowing with charm and character. It has a beach area and the town is loaded with boutiques and restaurants. Walk the streets and visit with the locals who always have a story to tell. Have a drink overlooking Lake Michigan or the Kalamazoo River. And check out the local artists and galleries. Vacation houses rented just on the outskirts allow you to experience the natural setting of Michigan with a quick drive to the downtown area.


  2. Milwaukee, Wisconsin

    Milwaukee is famous for beer so naturally it’s brimming with brew pubs. It also has first-class restaurants and a variety of ethnic food options. The downtown area is easy to walk around to get to many of the spots on your own. You can visit the historical Captain Frederick Pabst Mansion, or tour the Harley-Davidson Museum, which includes 20 acres, a restaurant, shops and plenty of motorcycles.

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  3. Starved Rock State Park, Illinois

    Walk on the wild side at Starved Rock State Park. Spend your weekend here hiking to see sandstone canyons, wildlife in a natural habitat and 14 waterfalls. Fish or paddle boat in the Illinois River. This is all just a 100-mile drive outside of Chicago. Leave the big city behind and get in touch with nature.

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  4. 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.


  5. 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.

Chicago is a great central location for taking weekend trips within a close driving distance. Take advantage of the surrounding areas and make it a vacation.