Best Weekend Trips
from Chicago, IL

Fodor's recommends the best weekend getaway ideas near Chicago, IL. Our itineraries include arts and culture, girl's getaway, and budget experiences.

  • Photo of Galena
    Galena

    Saved from the glaciers that flattened most of the Midwest, Galena boasts hills big enough for decent downhill skiing and an autumn beauty that draws fans far and wide. 85 percent of its 19th-century buildings are listed on the National Register of Historic Places. Visitors adore its small-town hospitality and romantic character.

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    • Distance: 164 miles
    • Best Time: June to October; December
    • Best for: Girl's Getaway Romantic Food and Wine
  • Photo of Indianapolis
    Indianapolis

    Indianapolis booms with visitors for big-time professional sports and the Indy 500, but here we've focused on family-friendly cultural and outdoor opportunities. White River State Park, multiple museums, an open-air music venue, and a promenade are perfect activities for a family getaway.

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    • Distance: 183 miles
    • Best Time: May to October
    • Best for: Family Arts and Culture Outdoor
  • Photo of Lake Geneva
    Lake Geneva

    From Gilded Age reminders and glacier-made beauty to spa-going and stargazing, Lake Geneva feels a world away from the Windy City. The Lake Geneva area, which includes adjacent Fontana and Williams Bay, welcomes visitors for rest and relaxation year-round.

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    • Distance: 80 miles
    • Best Time: June to September
    • Best for: Family Girl's Getaway Romantic
  • Photo of Milwaukee
    Milwaukee

    In Milwaukee, beer is still an important part of the city's fabric, but it has also morphed into a multi-faceted destination with world-class art and award-winning restaurants. Milwaukee prides itself on its distinctive neighborhoods, the Historic Third Ward being one of the trendiest with its galleries, caf├ęs, and boutiques.

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    • Distance: 93 miles
    • Best Time: May to October
    • Best for: Budget Arts and Culture Shopping
  • Photo of Saugatuck and Douglas
    Saugatuck and Douglas

    Just a mile apart, Saugatuck sees most of the bustle of activity, whereas Douglas is smaller and quieter. Together, they make up one of Chicago's favorite places for a nearby escape full of art galleries, incredible local eats and drinks, and outdoor options like exploring the local sand dunes and simply relaxing on the beach.

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    • Distance: 140 miles
    • Best Time: June to September
    • Best for: Arts and Culture Food and Wine Outdoor
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