Where to go to get away from it all, but not too far from Chicago, all year long

Whether seeking a spring getaway, a summer adventure, a scenic fall drive, or a cozy winter retreat, Chicagoans have no shortage of nearby destinations to explore in 2025. From charming towns and lush parks to picturesque lakesides and bustling cultural spots, there's always something new to discover just a short drive or train ride from the city. 

Spring:

Galena, Ill.

Just a three-hour drive from Chicago, Galena is a picturesque town nestled in the rolling hills of Northwest Illinois. Known for its 19th-century architecture, charming shops, and scenic views, it’s the perfect place to enjoy the blossoming season. Explore the historic downtown area, hike through Grant Park (there’s one there, too!), or enjoy wine tasting at one of the local wineries. Galena’s quaint atmosphere makes it an ideal spring retreat.

Starved Rock State Park, Ill.

Only a 1.5-hour drive from Chicago, Starved Rock is a popular spring destination for nature lovers. The park is known for its stunning waterfalls, especially in the spring when they’re flowing from the thawing snow. Enjoy hiking trails, wildlife watching, and the beautiful Illinois River views. With the park’s close proximity, it’s the perfect place to spend a day or weekend reconnecting with nature.

Summer:

Lake Geneva, Wis.

Just under two hours north of Chicago, Lake Geneva is an ideal summer destination for both relaxation and outdoor adventures. The crystal-clear waters of the lake are perfect for boating, kayaking, and fishing. If you prefer land activities, the area offers great hiking, bike trails, and golf courses. For those looking for something more luxurious, the town also features fine dining, boutique shopping, and resorts to relax after a day of outdoor fun.

Wisconsin Dells, Wis.

Known as the "Waterpark Capital of the World," Wisconsin Dells is a short 3.5-hour drive from Chicago and a perfect summer getaway for families. In addition to the world-famous indoor and outdoor waterparks, Wisconsin Dells offers boat tours, hiking trails, and the picturesque Mirror Lake State Park. The Dells is an action-packed destination, ideal for anyone seeking both thrills and outdoor exploration.

Lake County, Ill.

Just a short drive north, Lake County offers scenic lakes, historic sites, and trails. Visit Six Flags Great America in Gurnee or take a quiet walk around the forest preserves.

Fall:

Bloomington-Normal, Ill.

Bloomington-Normal, located just 2.5 hours from Chicago, offers an eclectic mix of culture, nature, and charm, making it a wonderful fall getaway. Take a stroll through the beautiful parks to see the changing autumn leaves, visit the McLean County Museum of History, or spend time exploring the local breweries. Fall in Bloomington-Normal is especially picturesque, with several nearby pumpkin patches and harvest festivals to check out.

The Great River Road, Illinois and Wisconsin

For an unforgettable autumn road trip, follow the Great River Road along the Mississippi River, just a short drive away. The drive offers breathtaking views of colorful fall foliage, especially near towns like Galena, Alton, and Nauvoo. Take a scenic detour to explore quaint riverfront towns, visit local wineries, and hike in areas like the Illinois Bluffs. This route is perfect for those wanting to experience the beauty of the Midwest during peak foliage season.

Winter:

Chicago’s Suburban Winter Escapes

You don’t have to leave the city to enjoy the winter season. Explore nearby suburban spots like Oak Park, Skokie, or Hinsdale for cozy cafes, shopping, and winter festivities. Oak Park, known for its Frank Lloyd Wright architecture, is especially charming in the winter, with local shops offering unique gifts and holiday displays. Skokie and Hinsdale are also great for winter strolls through parks or museum visits.

Lake Michigan Shoreline, Indiana Dunes National Park

Located just under an hour from Chicago, the Indiana Dunes National Park is a peaceful winter destination offering scenic walks along the frozen shores of Lake Michigan. The park offers winter hikes and birdwatching opportunities. It’s the perfect spot to escape the hustle and bustle of the city and enjoy the quiet beauty of nature during the coldest months.