The Windy City offers plenty of cultural, recreational, and culinary attractions, but destinations beyond the city limits let you explore the best of the region too. From national parks and destination-worthy wine regions to nearby cities, here are some of the most enticing day trips from Chicago.
Naperville – about 28 miles (45 kilometers) away
Head just outside Chicago city limits and venture to charming Naperville. The Chicago suburb, home to roughly 150,000 people, is a city in its own right. Trains link the two destinations, and full-day tours make getting there simple. Upon arrival, browse the shops and restaurants in Naperville’s downtown and stroll along the Riverwalk. For an unconventional way to explore the area, try a smartphone scavenger hunt game featuring Naperville’s key attractions.
Indiana Dunes National Park – about 49 miles (79 kilometers) away
Though Indiana Dunes National Park is only a quick drive around Lake Michigan’s southernmost shore from Chicago, the park feels a world away with its beachy ambiance and Saharan sand dunes. Enjoy a day at the beach; explore the titular dunes, marshes, and forests; and even discover (and taste) the highlights of the Duneland Wine Country on a full-day tour.
Milwaukee – about 83 miles (134 kilometers) away
Book a day trip to Milwaukee, Wisconsin, and head across state lines to discover another thriving city. As the historic home of the Miller Brewing Company, Pabst Brewing Company, and a slew of modern craft breweries, Milwaukee is renowned for its long-running beer scene. The cosmopolitan city also boasts the impressive Milwaukee Art Museum, soaring Milwaukee City Hall, and other attractions. A one-day tour is enough time to discover the highlights.
Southwest Michigan – about 90 miles (145 kilometers) away
Discover the thriving Great Lakes wine region, and sip in style on a full-day excursion from Chicago to scenic southwest Michigan. The Lake Michigan Wine Trail features dozens of banner wineries. Rieslings, pinot gris, and Rhone varietals are some of what’s planted on Michigan’s slopes, and you can find a selection of fruit wines and brandies, too. Head out on a full-day tour—and leave the driving to your guide.
Indianapolis – about 185 miles (298 kilometers) away
Indiana’s thriving state capital, Indianapolis offers one more incentive to travel across state lines. The accessible city is a popular choice for visitors of all ages as it's home to the famous Speedway, which hosts the Indianapolis 500, as well as museums and other cultural stops. Take part in a scavenger hunt game for a fun-filled sightseeing option, go on a guided walk of the Indy Beer Mile, or follow a local guide to the tasty eateries of Massachusetts Avenue.