Best Weekend Trips
from Chicago, IL

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.

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.

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.

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, cafés, and boutiques.

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.