24 Best Weekend Getaways from Chicago

When you’re looking for a change of scenery, Chicago’s energy and vibrancy can be hard to leave behind. Known as the birthplace of the skyscraper, the Windy City boasts award-winning restaurants, top-tier sports teams, and cultural treasures. However, if you’re ready to unwind, there are plenty of weekend getaways just a short drive away. Whether you crave outdoor adventure, small-town charm, or scenic escapes, these nearby destinations offer a refreshing retreat from the bustle of the big city.

Whether you want to find things to do in Chicago this weekend or venture out, this guide will help you plan. Explore nearby states like Indiana, Wisconsin, Michigan, and Iowa, or discover hidden gems right in Illinois. All of these locations can serve as the perfect reset, allowing you to enjoy a weekend away, free from the fast-paced city life.

About Two Hours or LexXss from Chicago

1. Fox River Valley, Illinois

For those who want something close to home, the Fox River Valley offers picturesque landscapes and countless outdoor activities. Known for the stuff to do in Chicago this weekend, it’s just a short trip to the valley. Spend your day hiking or biking along the Fox River Trail, and end with a cultural stop at Aurora’s Paramount Theatre for a Broadway-caliber show without the big-city prices.

2. Harbor Country, Michigan

About 70 miles from downtown Chicago, Harbor Country offers a relaxed atmosphere reminiscent of Chicago’s lakefront, but much quieter. Many locals looking for things to do in Chicago this weekend drive up to Harbor Country for beach walks, winery tours, or a visit to the charming town of New Buffalo.

3. St. Joseph, Michigan

St. Joseph offers a small-town experience with activities for the whole family. Known for its beach access and family-friendly restaurants, St. Joseph is an excellent spot for those seeking events in Chicago this weekend, or even just a change of pace. Grab pizza at Silver Beach Pizza or let the kids enjoy the Silver Beach Carousel while waiting for your table.

4. Milwaukee, Wisconsin

Just a two-hour drive from Chicago, Milwaukee is a city packed with beer culture, great museums, and waterfront attractions. Milwaukee offers so much to do, it’s a common answer to “what are the best things to do in Chicago this weekend?” Milwaukee offers cultural enrichment, outdoor markets, and brewery tours. Don’t miss a visit to the Harley-Davidson Museum or the Milwaukee Art Museum.

5. South Haven, Michigan

This beach town is known for its scenic views and relaxed vibe. Whether you’re in the mood for a beach day or the National Blueberry Festival, it’s a great alternative for those not wanting to deal with the Chicago shootings this weekend and instead seek relaxation by the water.

6. Starved Rock State Park, Illinois

For adventure lovers, Starved Rock offers a nature-filled escape about two hours from the city. Hike through the park’s canyons and waterfalls, especially popular for fall foliage. If you’re not feeling the urban events in Chicago this weekend, the natural beauty here is a refreshing alternative.

7. Gurnee, Illinois

Gurnee, Illinois If high-adrenaline adventure is more your style, Six Flags Great America in Gurnee offers thrilling roller coasters and family-friendly rides. Combine your amusement park fun with a stay at the Great Wolf Lodge for a weekend packed with excitement.

8. Wilmot Mountain, Wisconsin

Wilmot Mountain, Wisconsin In winter, Wilmot Mountain is a top destination for skiers and snowboarders. Just a short drive from Gurnee, Wilmot Mountain’s newly upgraded facilities make it a favorite for a snowy weekend retreat.

9. Lake Geneva, Wisconsin

Lake Geneva, Wisconsin Just a couple of hours from Chicago, Lake Geneva offers a mix of outdoor activities, from scenic lakefront strolls to boat tours. Stay at the Abbey Resort for a luxurious weekend getaway while soaking in the beauty of this Midwest treasure.

10. Grand Geneva Resort & Spa, Wisconsin

Grand Geneva Resort & Spa, Wisconsin Lake Geneva’s winter attraction, Grand Geneva Resort & Spa, is perfect for families and couples alike. The resort’s ski hill and spa facilities make it one of the top Midwest destinations for year-round relaxation and adventure.

About Three Hours or Less from Chicago

11. Turkey Run State Park, Indiana

For outdoor enthusiasts, Turkey Run State Park is a hidden gem. About 3 hours from Chicago, it’s perfect for those searching for a nature fix rather than traditional stuff to do in Chicago this weekend. Turkey Run offers rugged hikes and scenic landscapes along its sandstone cliffs.

12. The American Club Resort Hotel, Kohler, Wisconsin

The American Club Resort Hotel, Kohler, Wisconsin Kohler is known for luxury, and The American Club Resort Hotel provides just that. Indulge in world-class spa services, enjoy hydrotherapy at Kohler Waters Spa, and explore high-end bathroom designs at the nearby Kohler Design Center.

13. Whistling Straits Golf Course, Sheboygan, Wisconsin

Whistling Straits Golf Course, Sheboygan, Wisconsin A golfer’s paradise, Whistling Straits is considered one of the top public golf courses in the country. The picturesque course is located near the American Club, making Kohler a must-visit for a golf-centric getaway.

14. Saugatuck, Michigan

Known for its art galleries and LGBTQ-friendly community, Saugatuck is one of Michigan’s best-kept secrets. If you’re tired of the typical things to do in Chicago this weekend, Saugatuck offers a laid-back atmosphere, quaint shops, and beautiful beaches for relaxation.

15. Wisconsin Dells, Wisconsin

The “Waterpark Capital of the World,” Wisconsin Dells is perfect for families. Whether you’re looking for outdoor water parks or indoor options during cooler months, the Dells is a popular choice for those wondering about events in Chicago this weekend or planning a family escape. Stay at one of the many themed resorts for an unforgettable weekend trip.

About Four Hours or Less from Chicago

16. Parke County, Indiana

Parke County, Indiana Known as the covered bridge capital of the world, Parke County offers charming scenery and a taste of the past. Visitors come from all over to explore the county’s 31 historic covered bridges and enjoy the area’s annual fall festival.

17. Galena, Illinois

Escape to Galena, a charming town known for its rolling hills, bed-and-breakfasts, and historic homes. If the hustle and bustle of the things to do in Chicago this weekend aren’t appealing, this town will transport you to a more peaceful, slower-paced time.

18. Dubuque, Iowa

A visit to Dubuque offers a unique experience. Enjoy views of the Mississippi River or visit the Field of Dreams movie site. It’s a great escape from the noise of Chicago, especially for those avoiding concerns around Chicago shootings this weekend and looking for a quieter weekend.

19. Ann Arbor, Michigan

This quintessential college town is famous for its vibrant arts scene, independent bookstores, and music venues. Visit the University of Michigan Museum of Art or explore Graffiti Alley, a public art space perfect for photography.

20. Madison, Wisconsin

Known for its vibrant university atmosphere, Madison is both a college town and a cultural hub. If you’re not sure what stuff to do in Chicago this weekend, Madison offers a great weekend away filled with food markets, biking trails, and cultural sites.

About Five Hours or Less from Chicago

21. Traverse City, Michigan

Known for its wineries and scenic beauty, Traverse City is a longer drive but well worth it. If you’re tired of the same things to do in Chicago this weekend, take a trip here to explore Sleeping Bear Dunes and indulge in the local wine scene.

22. Louisville, Kentucky

For those looking for a longer trip, Louisville offers bourbon, history, and culture. Visit the Muhammad Ali Center or explore Whiskey Row for a unique experience compared to the typical events in Chicago this weekend.

23. St. Louis, Missouri

St. Louis is a major city escape, offering a mix of historical attractions and fun activities like the Gateway Arch and Forest Park. For travelers seeking things to do in Chicago this weekend but wanting a change of scenery, St. Louis offers plenty to explore.

A Quick Flight

24. Minneapolis – St. Paul, Minnesota

The Twin Cities provide an exciting mix of art, music, and outdoor activities. Catch a flight for a weekend and enjoy everything from Prince’s Paisley Park to the Mall of America. It’s an easy flight for those tired of searching for events in Chicago this weekend and ready to discover something new.

Whether you’re escaping the urban stress or just want to discover something beyond the typical stuff to do in Chicago this weekend, these destinations offer something for everyone. Plan your next weekend getaway and recharge away from the city buzz!

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