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We could all use an escape from the hustle and bustle of the Windy City every so often, so we’ve rounded up the best weekend getaways from Chicago. Whether you’re looking for beautiful landscapes or small-town charm, these weekend trips from Chicago are sure to please every type of traveler.

Indianapolis, Indiana
With just a three-hour drive from the city is the city of Indianapolis. “Indy” as called by locals, offers plenty to do. For kids, there is the Children’s Museum of Indianapolis and the famous Indianapolis Zoo.

The Broad Ripple neighborhood has nightlife, dining, shopping, and more for couples. It is the ideal place for a romantic getaway near Chicago. The Massachusetts Avenue Arts District offers theaters, galleries, and independent boutiques, this often is termed as the favorite family vacation spot near Chicago.

History lovers should book a stay in one of the 1920s Pullman train car rooms at the Crowne Plaza Indianapolis Downtown-Union Station.

Saugatuck, Michigan

If you are looking for a romantic getaway from Chicago, Saugatuck is the place for you. You can spend quality time together near this lakeside town, located just under two and a half hours from Chicago.

After a day of enjoying Lake Michigan’s pristine beaches, you can rest at the adorable inns or bed-and-breakfasts in the town.

Lake Geneva

Just like the name, this Geneva of the West is as picturesque as the Lake Geneva of Switzerland. This is another waterfront escape located just an hour and a half from Chicago.

Milwaukee, Wisconsin

A lot of people travel to Milwaukee as a weekend getaway from the hustle and bustle of the city.

Milwaukee is the beer hub of the US. Today, you can toast to the city’s beer heritage by trying these classics or visiting one of the many local craft breweries.


Madison, Wisconsin
Wisconsin's capital city is just over two and a half hours from Chicago. This city offers something for every traveler. Often food lovers head to the National Mustard Museum or try the fresh ice cream at the Sassy Cow Creamery, located 20 miles from Madison.

Families check out the Madison Children’s Museum and the Children’s Theater of Madison for kid-friendly entertainment. It is an ideal vacation spot near Chicago.

Holland, Michigan
Holland, Michigan is a unique weekend getaway destination, located under three hours from Chicago.

The yearly Tulip Time Festival is another great reason to visit Holland — six million tulips are planted across Holland, so visit in spring to see the beautiful flowers in bloom.

Indiana Dunes, Indiana
Just an hour from Chicago, Indiana Dunes National Park makes the perfect quick weekend getaway. This national park is often deemed as a romantic getaway for couples from Chicago.

You can even squeeze it in for a day trip if you’re short on time.
With an area of 15 miles of Lake Michigan’s shoreline, this national park makes up for an ideal relaxing weekend away from the city.

Go for a hike along the dunes, fly a kite on the beach, enjoy horseback riding, or check out the historic 1933 World's Fair Century of Progress Homes.

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