Side Trips from Chicago: Places to Explore


  • Galena, Illinois

    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. Bursting with charm, this small town... Read more

  • Indianapolis, Indiana

    Indianapolis is one of those places that residents don't want the masses to know about, lest they spoil its perfect blend of bustle and easygoing Midwest mentality that makes it such a livable and lovely... Read more

  • Lake Geneva, Wisconsin

    From Gilded Age reminders and glacier-made beauty to spa-going and stargazing, Lake Geneva feels a world away from it's nearest big-city neighbor, Chicago. In the early 20th century, the area was dubbed... Read more

  • Milwaukee, Wisconsin

    For anyone who was watching TV in the 1970s, Milwaukee will forever be associated with Happy Days and Laverne & Shirley, the BFFs who, fittingly, worked in a brewery. Indeed, beer still constitutes... Read more

  • Saugatuck, Michigan

    In Saugatuck, and neighboring Douglas, you'll find the streets chockablock full of art galleries, incredible local eats and drinks, and outdoor options like exploring the local sand dunes and relaxing... Read more