Trip Ideas

Top 5 Weekend Getaways From Chicago For People Who Really Need A Break

Although it may look like the Windy City is in the middle of nowhere from looking at a map, there are so many incredible weekend getaways from Chicago for people who want to go places and explore for a day or full weekend trip. Whether you’re looking for some beautiful scenery for hiking, some lovely beaches, or a cute small town to explore, there are some great spots within driving distance of the Windy City with something for everyone to enjoy.

1. Indiana Dunes State Park (Indiana)

Distance from downtown: 47 miles (approximately 1 hour in good traffic)

In addition to the beaches on Lake Michigan, the Indiana Dunes State Park is home to hiking trails and fascinating geographic features. The Dunes were formed by the southern winds blowing off of Lake Michigan, depositing sand over millennia as the winds hit the coastal vegetation.

On a clear day, you can see the Chicago skyline from the observation deck atop Mt. Tom, and there are great birdwatching and wildlife observation all year long. Although the beach is wonderful for swimming and sunbathing in the summer, you can also cross-country ski and snowshoe throughout the park in the winter months, and catch some gorgeous fall colors in late September – early October.

The surrounding area offers some gorgeous campgrounds, lodging, dining, and shopping if you need a break from being in the park before heading back into downtown.

2. Starved Rock State Park (Illinois)

Distance from downtown: 99 miles (approximately 1 hour and 45 minutes in good traffic)

Starved Rock State Park was voted the #1 attraction in the state of Illinois, so it’s definitely one of the better weekend getaways from Chicago. The park contains 13 miles of hiking trails and some breathtaking views, including waterfalls, which are most active in the spring due to meltwater and heavy rains. Of course, the park’s winding canyons and towering trees are beautiful year-round. If you’re lucky, you can see deer, wild turkeys, raccoons, eagles, and a variety of flora and fauna throughout the park.

The area played a significant role in the Native American history of Illinois. According to legend, in the late 18th Century, a group of Native Americans from the Illinois Confederation (also known as the Illiniwek) took refuge atop the butte, which was then besieged by the Ottawa and Pottawatomi until all of the Illiniwek had starved, resulting in the name “Starved Rock”. The area was later designated as a National Historic Landmark in 1960 and was added to the National Register of Historic Places in 1998.

After you’re done hiking and exploring the park and learning about the region’s Native American history, there’s loads of things to do in the surrounding town. Be sure to check out the local wineries, shopping, and historical sites before heading home to complete your trip.

3. Door County (Wisconsin)

Distance from downtown: ~250 miles (approximately 4 hours, depending on where in the peninsula you’re staying)

Door County is the farthest away of all our weekend getaways from Chicago to make this list, but is absolutely worth the drive up. From relaxing next to the water, fishing, hiking, kayaking, hopping on a boat to take in all of the gorgeous scenery, and partaking in some more adventurous water sports like jet skiing or parasailing when the weather cooperates—there’s something for everyone to enjoy. Door County is also home to several breweries and wineries, which are perfect escapes from the elements when the temperatures dip.

There are actually several cities that make up Door County. If you’re looking for some nightlife in addition to a relaxing escape from the city, be sure to stay near Fish Creek, known for its shopping and vibrant bar scene, in addition to its proximity to Peninsula State Park. If you’re more of a foodie, be sure to check out Sister Bay, known for its spectacular dining in addition to its natural beauty. If you’re looking for something a little quieter and remote, plan to stay in Jacksonport, where it’ll just be you and the water.

Door Country is beautiful all year round, although it’ll definitely be a bit chilly in the winter months. If it’s too cold for swimming and sunbathing to be an option, you can still explore the peninsula by snowmobile or cross-country ski, and you won’t have to fight the large summer crowds.

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4. Lake Geneva (Wisconsin)

Distance from downtown: 83 miles (approximately 1 hour and 45 minutes in good traffic)

Named after its counterpart in Switzerland, Lake Geneva, Wisconsin is a much smaller but equally as delightful a vacation destination. The small town is home to many Gilded Age mansions built by rich Chicagoans looking to escape the hustle and bustle of downtown. Some of the estates are open to the public for tours—perfect for the architecture and history buffs.

The area became popular for a reason—the large lake features many sandy beaches and allows for many aquatic activities, such as water skiing, boating, canoeing and kayaking, and many others. The lake freezes over in the winter, making it a great spot for ice fishing. In addition, there are some great spots to ski, snowboard, and sled in the surrounding hills.

The small town of Lake Geneva is home to dozens of fine restaurants, as well as many resort and spa properties to help you properly relax during one of your weekend getaways from Chicago.

5. Galena (Illinois)

Distance from downtown: 170 miles (approximately 3 hours in good traffic)

Galena, Illinois is listed on the National Register of Historic Places and is a wonderful small town to explore while taking a break from the city. The city is named after the mineral “galena”, which is mined in the area and was the cause of the first major mineral rush in the United States back in the early 19th Century. At one point, Galena’s population even rivaled that of Chicago (although that’s now hard to believe).

This tiny town (now home to around 3,500 people) was once home to Ulysses S. Grant and eight other Civil War generals, and was the largest steamboat hub north of St. Louis. Today, the town has been restored and is now home to a multitude of restaurants, shops, and museums to explore the rich history of the region.

Know of any more great weekend getaways from Chicago and want to share? Comment below!

Suggested next reading: 5 Incredible Chicago-Style Foods You’ve Got To Try In The Windy City

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