The Best Labor Day Getaways Under 3 Hours From Chicago

Still looking for the perfect Labor Day getaway?

We’re here to help. Check out our list of favorite spots to spend the long weekend away from the city.

Milwaukee, Wisconsin

Breweries? Check. Museums? Check. Kayaks? Yes, please. Milwaukee is the Chicagoan go-to for a quick weekend away from the city, and it’s easy to see why!


Galena, Illinois

History, wine tasting, shopping, and gorgeous bed & breakfasts are the situation in Galena. You can’t go wrong!


Saugatuck, Michigan

Little shops, ice cream spots, and plenty of beaches to relax at. Saugatuck is the perfect spot to spend your long weekend.


Ottawa, Illinois

Spend the day hiking Starved Rock, then drive over to Ottawa to check out Tangled Roots Brewing for some unique brews.


Michigan City, Indiana

Does somewhere on a beach sound like your ideal weekend? Michigan City is the best place to put your toes in the sand. Relax at the Dunes before heading to the casino!


Sawyer, Michigan

Drop by the iconic Round Barn estate for wine tastings, relax at the Warren Dunes, or hike the Warren Woods. The options in this sweet Michigan town are endless.


New Buffalo, Michigan

Another Chicagoan and Midwestern favorite, New Buffalo has everything you could need: the beach, good food, and plenty of local spots to check out.

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