Top 21 Day Trips Near Chicago to Explore in 2025

Welcome to the Windy City! Whether a local or a traveler eager to explore beyond the skyline, our guide to the best day trips from Chicago is your ticket to adventure. We’ll show you how to swap city streets for scenic escapes, all within a day’s reach of Chicago. From charming small towns to natural wonders, get ready to discover the Midwest’s most unforgettable experiences. Pack your sense of adventure, and let’s hit the road – Chicago-style day trips await!

1. Milwaukee, WI

Milwaukee is a significant city located on the shores of western Lake Michigan, just a 1.5-hour train ride or drive north of Chicago. We’d suggest catching the train if possible, as Milwaukee is renowned for its breweries. Taking guided brewery tours is one of the best things to do in Milwaukee. However, it also features the Holler House, the Milwaukee Art Museum, and the Harley-Davidson Museum, which showcases a stunning collection of motorcycles and highlights iconic biker culture.

• Distance from Chicago: 1.5 hours
• How to get there: Train, bus, or coach

2. South Bend, IN

South Bend offers a different vibe as a university city located on the St. Joseph River. It is perfect if you are seeking a more laid-back experience. You can explore the iconic University of Notre Dame campus, featuring a classic gold-domed building. Additionally, the city center showcases local history, including car manufacturing artifacts at the Studebaker National Museum.

• Distance from Chicago: 2 to 3 hours
• How to get there: Car or train

3. Madison, WI

Madison may be small but it’s the capital city of Wisconsin. This charming city features beautiful architecture, including the historic domed Wisconsin State Capitol. Moreover, you can enjoy the Capital City State Trail and visit Olbrich Botanical Gardens. Madison is your ideal choice if you desire a political sightseeing day trip from Chicago.

• Distance from Chicago: 2 to 4 hours
• How to get there: By car or shuttle bus

4. Starved Rock State Park, IL

Starved Rock State Park is one of Illinois’ most popular natural attractions. Nestled along the Illinois River, it features remarkable sandstone canyons amidst vibrant forests. The park is perfect for exploring nature, thanks to its extensive network of hiking trails, marked boardwalks, and stunning waterfalls. Nature lovers will appreciate the abundant wildlife and stunning landscapes.

• Distance from Chicago: 1.5 hours
• How to get there: Car

5. Cedarburg, WI

Cedarburg boasts charming aesthetics reminiscent of a movie set, with its old-school-style houses and vibrant atmosphere. Founded in the 1840s, this town offers a wonderful mix of local charm, brewery and winery tours, as well as unique attractions like the Wisconsin Museum of Quilts and Fine Arts. Cedarburg is truly a memorable day trip from Chicago.

• Distance from Chicago: 2 hours
• How to get there: By car

6. Illinois Beach State Park, IL

If you’re looking for a relaxing beach day, Illinois Beach State Park should be on your list. Encompassing over 4,000 acres, it features scenic hiking trails and picturesque shorelines along Lake Michigan. Start with a leisurely hike, then enjoy the beach or even stay overnight to fully immerse yourself in nature.

• Distance from Chicago: 1 hour
• How to get there: By car

7. Lake Geneva, WI

Lake Geneva is a beautiful resort city situated along the banks of Geneva Lake, northwest of Chicago. Once a retreat for wealthy Chicago residents, this city features stunning Gilded Age mansions and a picturesque Shore Path. Enjoy the local beaches and unwind before heading back to Chicago’s bustling atmosphere.

• Distance from Chicago: 1.5 hours
• How to get there: By car

8. Rockford, IL

Rockford, located on the banks of the Mississippi River, is known for its rich history and numerous attractions. This vibrant city features the koi ponds at Anderson Japanese Gardens, numerous public parks, and the Rockford Art Museum. Combining a trip to Rockford with a visit to Madison is highly recommended.

• Distance from Chicago: 1.5 hours
• How to get there: By car

9. Indiana Dunes National Park, IN

For those who appreciate natural beauty, Indiana Dunes National Park is a must-visit destination. This scenic park encompasses 15 miles of stunning shoreline along Lake Michigan, and it’s perfect for swimming or hiking. Additionally, it’s a great spot for birdwatching, making it a perfect spot for nature lovers.

• Distance from Chicago: 50 minutes
• How to get there: By car

10. Lakeshore State Park, WI

Lakeshore State Park is an urban oasis located just off Milwaukee’s shoreline. Best explored on foot, this park offers beautiful views of the city skyline and Lake Michigan. It’s an ideal choice for a romantic picnic during sunset or a leisurely stroll through nature.

• Distance from Chicago: 1.5 hours
• How to get there: By car

11. Monroe, WI

Monroe, recognized as the Swiss cheese capital, is a delightful city with a rich dairy farming history. Don’t miss the National Historic Cheese Making Center Museum and the Chalet Cheese Cooperative. The historic architecture adds to the charm, making Monroe a unique destination for foodies and history enthusiasts alike.

• Distance from Chicago: 2 hours
• How to get there: By car

12. St. Joseph, MI

St. Joseph is a picturesque coastal city along Lake Michigan, featuring beautiful attractions like Silver Beach County Park. Here, you can enjoy the charming beach, a vintage carousel, and stunning waterfront views, making St. Joseph an ideal seaside escape from Chicago.

• Distance from Chicago: 1.5 hours
• How to get there: By car

13. Channahon State Park, IL

Channahon State Park is a unique destination showcasing Illinois’ canal history. Surrounded by scenic trails, waterfalls, and wildlife, it’s just a short drive from Chicago. The park features a restored lock tender’s house, providing a glimpse into the area’s historical significance.

• Distance from Chicago: 50 minutes
• How to get there: By car

14. Oak Park, IL

Oak Park is a charming village filled with stunning architecture. Visitors can explore attractions like the Frank Lloyd Wright Home and Studio as well as Ernest Hemingway’s Boyhood Home. Conveniently accessible from central Chicago, it’s an ideal spot for culture and history enthusiasts.

• Distance from Chicago: 15 to 20 minutes
• How to get there: By train

15. Grand Rapids, MI

Grand Rapids features a dynamic cultural scene, with museums, art galleries, and a beautiful riverside setting. Known for its breweries, you can opt for guided tours or simply explore the city at your own pace. Whether driving or taking a shuttle, make sure to enjoy this vibrant city.

• Distance from Chicago: 3 to 5 hours
• How to get there: By car or shuttle

16. Windmill Island Gardens, MI

Windmill Island Gardens, featuring a 250-year-old windmill, is a celebration of Dutch heritage. Located near Holland, Michigan, visitors can enjoy self-guided tours and scenic gardens, especially stunning during springtime. It’s perfect for a themed day trip from Chicago.

• Distance from Chicago: 2.5 hours
• How to get there: By car

17. Galena, IL

Galena is a charming small town with rich Civil War history. As the former home of General Ulysses S. Grant, this town features scenic 19th-century architecture and a vibrant downtown filled with shops and historical landmarks. It’s a delightful day trip for history lovers.

• Distance from Chicago: 2 hours and 45 minutes
• How to get there: By car

18. Michigan City, IN

Michigan City is conveniently located just an hour away from Chicago, making it an excellent choice for a quick getaway. The city features beautiful beaches, picturesque lighthouses, and the Barker Mansion, showcasing 19th-century elegance. It’s a charming location for a beach day.

• Distance from Chicago: 1 to 2 hours
• How to get there: 1 hour by car or 2 hours by train

19. Peoria, IL

Peoria, situated along the Illinois River, offers lovely riverside parks and a historical atmosphere. Perfect for a day trip, it’s best reached by car from Chicago, allowing for a scenic journey through the heart of Illinois.

• Distance from Chicago: 2.5 hours
• How to get there: By car

20. Six Flags Great America, IL

For a day filled with excitement, Six Flags Great America offers thrilling rides and entertainment. It’s perfect for families and those seeking an adrenaline rush, conveniently located just north of Chicago.

• Distance from Chicago: 1 to 2 hours
• How to get there: 1 hour by car or 2 hours by train then bus

21. Glacial Park Conservation Area

Glacial Park is a stunning 3,400-acre reserve, ideal for photography and outdoor adventures. With its mix of wetlands and prairie, you can explore by hiking or canoeing. It’s a perfect place to escape the city and immerse yourself in nature’s beauty.

• Distance from Chicago: 1 hour and 20 minutes
• How to get there: By car

There’s so much to experience on day trips from Chicago—whether that’s Dutch heritage, rich history, or enjoying a day at an amusement park. With stunning natural beauty and vibrant local attractions within arm’s reach, there are plenty of opportunities for adventure. Make sure to explore the diverse offerings that surround this iconic city!