Feeling cooped up in the city and longing for an autumn escape for a day?

We’ve handpicked 15 top self-drive day trips around Chicago, perfect for any season—especially fall!

From hiking through colorful autumn forests and exploring charming, festively decorated towns to cozy indoor attractions and thrilling seasonal events—get ready to discover the best-hidden gems and popular destinations just a short drive from Chicago!

1. Starved Rock State Park in Illinois (2-3 Hours)

Fall highlights: Witness breathtaking fall foliage as the trees transform into a vibrant palette of reds, oranges, and yellows. The park also hosts fall festivals and guided hikes that showcase the season’s beauty.

Starting at number one, we have Starved Rock State Park! With 15 miles of trails, you’ll be surrounded by lush forests, towering sandstone bluffs, and stunning waterfalls.

Visit Lover's Leap Overlook for breathtaking views of the Illinois River. Pack a picnic and join a guided tour to uncover the park's rich history and geology. In addition to hiking, the park offers fishing, boating, and camping facilities.

2. Indiana Dunes National Park in Indiana (1 Hour)

Fall highlights: Explore the park's stunning fall colors along the dunes and trails. Cooler temperatures make for comfortable hikes, and the park’s autumn bird migration offers fantastic birdwatching opportunities.

For a beach day, Indiana Dunes National Park is ideal even in the Fall! With 15 miles of sandy shores along Lake Michigan, it’s perfect for swimming, sunbathing, and beachcombing.

Over 50 miles of trails are also available for hiking, bird watching, and exploring diverse habitats. Don't miss climbing the dunes for a workout and stunning views. The visitor center is packed with information about the park's unique ecology and history.

Besides the beach, you can explore forest trails as well as nearby towns for local dining and shopping.

3. Milwaukee, Wisconsin (1 Hour)

Fall highlights: Enjoy Milwaukee’s fall festivals, like Oktoberfest, and explore the art galleries while cozying up in cafes during crisp autumn days.

When you're ready for some culture, Milwaukee is bursting with art and history. Begin your adventure at the Milwaukee Art Museum, home to over 30,000 works of art and a jaw-dropping architectural design by Santiago Calatrava.

Then, head to the Historic Third Ward, a treasure trove of trendy shops, galleries, and the bustling Milwaukee Public Market.

History buffs will enjoy the Milwaukee Public Museum's extensive exhibits, which include a life-sized replica of old Milwaukee and a captivating butterfly exhibit.

4. Holland, Michigan (2-3 Hours)

Fall highlights: The town’s charming downtown becomes even cozier with fall decorations and autumn festivals, and nearby farms offer pumpkin picking and hayrides. Holland State Park’s trails offer a scenic fall backdrop along Lake Michigan.

Looking for a touch of Europe? Holland, Michigan, known for its tulip festival each spring, offers a unique charm all year long.

Windmill Island Gardens features an authentic Dutch windmill and beautiful gardens.

Take a stroll through downtown Holland, filled with delightful shops, restaurants, and cafes. Make sure to try some traditional Dutch pastries like stroopwafels and poffertjes.

Holland State Park, with its stunning beach on Lake Michigan, also offers opportunities for swimming, picnicking, and hiking along scenic trails. This town's unique charm and welcoming vibe make for a delightful day trip.

5. Lake Geneva, Wisconsin (2 Hours)

Fall highlights: Take a boat tour on Lake Geneva to see the stunning fall foliage. The town’s Oktoberfest and fall-themed festivals add to the charm, with cozy shops and cafes to warm up in afterward.

For outdoor enthusiasts, Lake Geneva is the ultimate destination! The lake is perfect for boating, fishing, and swimming. Rent a boat or take a guided tour to soak in the scenic beauty of the clear waters and surrounding landscapes.

The Geneva Lake Shore Path is a unique way to explore the area. It offers a 21-mile trail through the yards of historic estates. Downtown Lake Geneva is also packed with shops, restaurants, and entertainment, so don't miss out!

6. Midewin National Tallgrass Prairie in Illinois (1 Hour and 30 Minutes)

Fall highlights: Experience the beauty of the prairie grasses turning golden and red in fall. Fall bird migrations and guided tours make this season a special time for nature enthusiasts.

Nature enthusiasts will love Midewin National Tallgrass Prairie where you can actually see bison in their natural habitat in Illinois.

With miles of trails for hiking, biking, and horseback riding, it's one of the largest open spaces near Chicago.

Discover the prairie’s rich history and natural beauty as you explore the vast grasslands and restored ecosystems.

Bird watching is a treat here, with many species calling the prairie home. In addition to hiking, you can attend educational programs and guided tours to learn about restoration efforts and the importance of prairie ecosystems.

7. Shipshewana (Indiana) (2-3 Hours)

Fall highlights: This charming Amish town hosts fall festivals, pumpkin patches, and beautiful country roads lined with autumn colors.

Just over two hours from Chicago, Shipshewana offers a peaceful retreat with local shops, bakeries, and a glimpse into Amish culture during the fall months.

Enjoy authentic Amish dining experiences or explore the local quilt shops for a cozy autumn vibe. You can also visit the indoor flea markets (check for days of operation) or take a horse-drawn buggy ride.

8. Kankakee, Illinois (1 Hour)

Fall highlights: Enjoy Kankakee River State Park’s vibrant fall foliage while hiking or fishing. The cooler weather makes exploring the town’s historical sites even more enjoyable, and local fall festivals add seasonal charm.

For a mix of history and outdoor activities, head to Kankakee. Start at the Kankakee Railroad Museum to dive into the area's rich railway history. The museum offers interactive exhibits and vintage train cars that kids and adults will both enjoy.

The French Heritage Museum is another must-see, showcasing the local French-Canadian culture and the region’s early settlers.

Besides the museums, the Kankakee River State Park is ideal for outdoor fun. Enjoy hiking, fishing, and canoeing in a beautiful setting along the Kankakee River.

9. Oglesby, Illinois (2 Hours and 30 Minutes)

Fall highlights: Matthiessen State Park becomes a photographer’s dream with its colorful fall foliage. Fall weekends bring fewer crowds, making it an ideal time for peaceful hikes.

Oglesby offers scenic parks and a rich history. Matthiessen State Park is a highlight, with trails, canyons, and waterfalls. It's a perfect spot for hiking, photography, and soaking in nature’s beauty.

The park is divided into the Dells and River areas, each offering unique landscapes and experiences.

Explore the unique geological formations and diverse habitats that make Matthiessen State Park a fascinating destination. Besides hiking, you can enjoy picnicking and horseback riding in designated areas.

10. Morton Arboretum (Under an hour)

Fall highlights: Explore over 1,700 acres of stunning fall colors as the trees burst into vibrant reds, oranges, and yellows. Seasonal events like the Glass Pumpkin Patch and evening Illumination walks make it a perfect fall destination.

Just 45 minutes from Chicago, Morton Arboretum offers beautiful walking trails, family-friendly activities, and peaceful spots to enjoy the autumn landscape.

You can also visit the Children's Garden and enjoy interactive exhibits that make it fun for all ages.

11. Cantigny Park, in Wheaton, IL (Under an hour)

Fall highlights: The gardens at Cantigny Park come alive with the warm hues of fall. Explore the stunning display of chrysanthemums, enjoy fall-themed events, or take a leisurely stroll through the grounds.

Only an hour from Chicago, Cantigny features gardens, museums, and nature trails that are perfect for a relaxing fall day trip.

Don’t miss the First Division Museum, which offers fascinating military history. Check their website for dates of historic military reenactments and other events.

12. Rock Cut State Park in Illinois (1 hour)

Fall highlights: The park’s 3,000 acres of forests transform into a beautiful fall landscape, offering scenic views from hiking and biking trails. Bring a picnic and enjoy the peaceful autumn atmosphere by the lakes.

Located just under two hours from Chicago, Rock Cut State Park is ideal for outdoor enthusiasts, with opportunities for fishing, hiking, and boating in a serene fall setting.

The tranquil Pierce Lake offers great opportunities for kayaking while soaking in the autumn scenery.

Which Day Trip Will You Choose?

These fantastic destinations offer an array of experiences, from outdoor adventures to cultural treasures. Each spot is just a short drive from Chicago, making them perfect for a spontaneous day trip.

Whether you’re looking to hike scenic trails, relax on sandy beaches, or explore charming towns, there’s something here for everyone. Pack your bags, gather your friends or family, and embark on an unforgettable adventure.

If you're bringing elders along, check out our guide to Chicago's best attractions for seniors.

The Midwest’s hidden gems await your discovery. Enjoy the diverse beauty and unique attractions these places offer.

12 Top Day Trips Around Chicago For Fall