9 of the Top Day Trips From Chicago

If you only have time for a short trip from Chicago, then Oak Park, located just west of the city proper, is an ideal destination—especially if you’re an architecture fan. Some 30 different homes and buildings here were designed by Prairie School luminary Frank Lloyd Wright, including his own Home & Studio. If you’re especially pressed for time, book a drive-by tour of the Frank Lloyd Wright Historic District; if you want a deeper look, you can also explore his Home & Studio with a guide.

Did you know?: Frank Lloyd Wright wasn’t the only famous Oak Park denizen—the village is also home to the Ernest Hemingway Birthplace Museum.

Visiting the Windy City with kids? Naperville, a city located in Chicago’s western suburbs, is just a short drive (or one-hour train ride) away and full of family-friendly attractions. Young kids will appreciate the DuPage Children’s Museum and the Naper Settlement (an open-air, living history museum). Nearby, the Morton Arboretum is an internationally acclaimed botanical garden with plenty of room to play, and the Knoch Knolls Nature Center offers free nature discovery days for young visitors. But there’s still plenty to tempt adults, from the city’s Riverwalk and buzzing downtown to popular craft breweries such as Solemn Oath.

Another easy day trip from Chicago is Evanston, situated on Lake Michigan’s North Shore and just a few miles from city limits. Accessible via the CTA’s Purple Line and Metra commuter trains, this academic destination is best-known as the home of top-ranked Northwestern University, whose tree-lined, sculpture-filled campus is open to visitors. But that’s not the only show in town. Other highlights range from the Baha'i House of Worship in nearby Wilmette—a beautifully ornate house of worship surrounded by pretty gardens—to the historic Grosse Point Lighthouse and Space, an intimate venue that regularly hosts events such as live music and comedy shows.

Joliet is steeped in American lore. The iconic Route 66 once passed through the Illinois city (and the Illinois Route 66 Scenic Byway still does today), while bison still roam at the nearby Midewin National Tallgrass Prairie.

Joliet also boasts a famous filming location from the 1980 movie The Blues Brothers: the Old Joliet Prison, which is still open to film buffs as well as fans of all things macabre. Joliet is also home to the Chicagoland Speedway, which hosts events from demolition derbies all the way up to NASCAR races, so it’s safe to say few other one-day trips from Chicago serve up as much variety—and quirk.

It’s hard to find a better nature day trip from Chicago than Rockford. Located less than two hours northwest of the Windy City by car, Rockford offers green escapes for outdoorsy types of all stripes. After a tranquil garden experience that’s especially photo-worthy? Venture to the Anderson Japanese Gardens. Looking for kid-friendly walking trails? Head to the Klehm Arboretum & Botanic Garden. Want something a little more rugged? Rock Cut State Park boasts rolling plains and hiking trails, plus lakes, dense forests, and abundant wildlife.

The great thing about planning a weekend getaway near Chicago? The Windy City’s location makes it easy to cross state lines and open yourself up to a whole new world of discovery. Case in point: It’s just a two-hour drive to South Bend in neighboring Indiana. Sports fans can make a pilgrimage to the University of Notre Dame, while museum lovers will have plenty to see and learn at the History Museum and the Studebaker National Museum. For a dose of (sandy) nature, swing by Warren Dunes State Park on your way back to Chicago.

Milwaukee isn’t just a vibrant destination for urbanites—it’s one of the best day trips from Chicago, full stop. It helps that the city offers something for everyone: Culture fans can drop by the Milwaukee Art Museum, sports enthusiasts can catch a Brewers game at American Family Field, gearheads can drop by the Harley-Davidson Museum, and suds lovers can drink their way through this historic brewing city. Round it all out with a guided walking tour—or a late-night ghost tour.

Insider tip: Plan to immerse yourself in this Midwestern city’s famous beer scene? Don’t worry about driving—Milwaukee is directly accessible from Chicago via a regular Amtrak train service, with a journey time of just an hour and a half.

Related: Visiting Milwaukee for the First Time? Here’s What To See and Do

Where Milwaukee serves up urban delights, Wisconsin’s capital city of Madison offers a charming mix of stately landmarks and scenic nature experiences. Madison is technically situated on an isthmus, and its five surrounding lakes offer picturesque sightseeing (and plentiful kayaking opportunities). Equally scenic is the Memorial Union Terrace on the University of Wisconsin–Madison campus—not to mention the Wisconsin State Capitol, whose grand dome can be seen as part of a walking or e-bike tour. But even if bad weather forces you inside, there are plenty of free museums to discover, including the Madison Museum of Contemporary Art and the Chazen Museum of Art.

One of the top attractions near Chicago for oenophiles is the Lake Michigan Shore Wine Trail—and St. Joseph, Michigan is the perfect jumping-off point for a tasting tour. With a designated driver in tow, you can travel among the region’s 15 member wineries, admiring the Lake Michigan shoreline views along the way. But even if you’re not a wine lover, there’s still plenty to do in this beachy destination. Lounge on the sand at the Silver Beach County Park, rent a boat for an aquatic outing, or visit the two historic St. Joseph Lighthouses.