9 Fun & Interesting Day Trips From Chicago

There’s no shortage of fun family things to do in Chicago, but sometimes you just need a break from the big city. Are you looking for something fun and interesting to do outside of Chicago?

There are plenty of interesting day trips within Illinois and the surrounding states that are just a short drive away.

Here are nine of our favorite day trips, all within 3 hours from the Windy City with superb scenic driving routes and byways, interesting historic towns and sensational state parks to explore.

Best Day Trips From Chicago

Starved Rock State Park, IL

Distance from Chicago: 93 miles via I-55/I-80 (1 hour 30 minutes)

Starved Rock State Park is about an hour and a half drive from Chicago, in the town of Oglesby, Illinois. The park gets its name from the sandstone cliffs that tower over the canyons and rivers below.

It’s a favorite among hikers, with over 13 miles of trails where you can traverse through canyons and see waterfalls created by melting glaciers. You might even spot a bald eagle or two if you’re lucky.

There are plenty of things to do in the park besides hiking. In the winter, you can go cross-country skiing or snowshoeing. And in the summer, you can cool off with a swim in one of the many swimming holes.

There are also boat tours available that take you through the canyons on the Illinois River.

If you’re looking for a longer trip, there are camping sites available in the park. Or, you can stay in one of the many lodges or cabins that are located nearby.

Galena, IL

Distance from Chicago: 163 miles via I-90/US-20 (2 hours 45 minutes)

Galena is a small city located in northwestern Illinois, about 3 hours from Chicago. It’s known for its stunning bluffs along the Galena River, its rich history dating back to the early 19th century, and warm, welcoming residents.

The city was once a booming lead mining town and was even home to President Ulysses S. Grant. Today, it’s a popular tourist destination for its historic downtown area and its scenic setting in the Driftless Area of Illinois.

USA Chicago Day Trips - fields overlooking Galena

While it may be small, Galena certainly packs a punch when it comes to things to do. Stroll down Main Street, lined with over 100 specialty shops, art galleries, and restaurants.

Be sure to stop in at the Galena Canning Company, a family-owned business that has been canning fruits and vegetables for three generations. Their biggest seller is the Apple BBQ Sauce, perfect for summer grilling.

Take a tour of the Ulysses S. Grant Home, or learn about the city’s history at the Galena History Museum. Galena is also home to five wineries, some of which offer tours and tastings. With vineyards nestled in the rolling hills, these wineries offer stunning views along with their delicious wines.

For some outdoor fun, hike around nearby Apple River Canyon State Park or take a Mississippi River Cruise.

Kalamazoo, MI

Distance from Chicago: 147 miles via I-94 (2 hours, 25 minutes)

If you’re looking for something a little more offbeat, consider a trip to Kalamazoo, Michigan. This quirky city is about 2.5 hours from Chicago and is known for its arts scene, craft beer breweries, and unique attractions.

One of the most popular things to do in Kalamazoo is visit one of the many craft breweries. Some of our favorites include Bell’s Brewery, Saugatuck Brewing Company, and the Kalamazoo Beer Exchange. Brewery tours are a great way to learn about the brewing process and taste some delicious beer.

Art lovers will want to check out the Kalamazoo Institute of Arts. The KIA is a world-renowned art museum with a collection of almost 5,000 works of art. Or maybe grab an ice cream and take a stroll to enjoy some of the many outdoor sculptures scattered throughout the city.

Kalamazoo isn’t all city, though! Surrounded by beautiful lakes, parks, and hiking trails, you can go swimming, kayaking, or stand-up paddle boarding on one of the nearby lakes in the summer. Its one of the best hidden gem family vacation spots in the Midwest.

And in the winter, there’s no shortage of outdoor activities either – hit the slopes at Timber Ridge ski area or go cross-country skiing at Fort Custer State Park.

Arthur, IL

Distance from Chicago: 174 miles via I-57 (2 hours 45 minutes)

Located in the heart of Illinois, Arthur is located less than 3 hours south of Chicago and is home to Illinois’ largest and oldest Amish community.

The Amish are a group of religious people who live simple lives without many modern conveniences. They are known for their handcrafted furniture, quilts, and delicious baked goods.

USA Chicago Day Trips - Amish Country around Arthur IL

A visit to Amish Country is like stepping back in time. There are no stoplights or billboards, and horse-drawn buggies are a common sight on the roads.

Be sure to explore some of the small towns and see the amazing handiwork of the Amish artisans. You can also take a tour of an Amish farm or go on a horse-drawn buggy ride.

For those looking for a more active experience, there are plenty of options, from hiking and biking trails to canoeing and fishing on Lake Shelbyville. And if you happen to be in town during the summer, the Arthur Strawberry Jam Festival is a must!

Springfield, IL

Distance from Chicago: 201 miles via I-55 (3 hours)

Located just 3 hours from Chicago, Springfield is the capital city of Illinois. The city is known for its many historical sites and museums, including the Abraham Lincoln Presidential Library and Museum, which chronicles the life of America’s 16th president.

Springfield was also home to President Barack Obama during his time as an Illinois state senator.

In addition to its presidential history, Springfield is also home to a number of other interesting attractions. Explore the Dana-Thomas House, designed in 1902 by renowned architect Frank Lloyd Wright and one of the best examples of his work.

Shop till you drop on vibrant Sixth Street where you’ll find everything from unique boutiques to mainstream retailers.

For some outdoor fun, hike or bike through one of Springfield’s many parks, including Lincoln Memorial Gardens, with 6 miles of trails around a pond or stop to smell the roses (or any of the other 1800 plants species) at Washington Park Botanical Garden.

And no trip to Springfield would be complete without a stop at Cozy Dog Drive In, the home of the original corn dog in operation since 1946!

Kankakee, IL

Distance from Chicago: 60 miles via I-57 (1 hour)

Just an hour south of Chicago, Kankakee is a small city with a number of historical sites, including the Kankakee Railroad Museum, which chronicles the history of the local railroads.

Architectural buffs will enjoy the B. Harley Bradley House, designed by architect Frank Lloyd Wright, along with the many custom-built Victorian era homes along the riverfront.

USA Chicago Day Trips - Kankakee River State Park

Kankakee is also a great place for nature lovers. The Kankakee River Trail is a 10-mile walking path perfect for a leisurely stroll or to go for a run.

Look for the Rock Creek Suspension Bridge, originally built in 1929, which spans 75 feet across the river at a height of about 75 feet.

For a more active experience, rent a kayak or canoe and paddle down the river, or try catching dinner on a fly fishing tour.

Rockford, IL

Distance from Chicago: 89 miles via I-90 (1 hour 35 minutes)

Just a short drive from Chicago, Rockford is the third largest city in Illinois and the county seat of Winnebago County.

The city is home to several historical sites, including the Midway Village Museum, which chronicles the area’s history from the days of the Native Americans through the present day.

Rockford is also a great place for nature lovers with its many parks and trails, including Sinnissippi Park, situated along the Rock River. The park is perfect for hiking, biking, fishing, or just enjoying a picnic lunch.

Be sure to stop by the Nicholas Conservatory & Gardens to enjoy its orchid gardens and butterfly house.

Families will want to check out the Burpee Museum of Natural History. Open since 1942; this museum is home to a wide variety of exhibits, including a hands-on discovery center for kids. Spend an afternoon learning about dinosaurs, mammals, and reptiles from around the world.

Holland, MI

Distance from Chicago: 152 miles viaI-94E & I-196 (2 hours 30 minutes)

Holland is a charming city situated on the shores of Lake Michigan, about 2.5 hours from Chicago. This quaint town is known for its Dutch heritage and culture and feels like you’ve been transported to the Netherlands.

USA Chicago Day Trips - Holland

It’s home to a number of Dutch-themed attractions, including the Dutch Village, which features a replica of a traditional Dutch windmill. Visitors can also take a tour of the Windmill Island Gardens to learn about the history of the area’s Dutch settlers.

Holland is also known for its tulips! Every April to May, the city celebrates Tulip Time with parades, music, and plenty of tulips. Be sure to check out Veldheer’s Tulip Garden, one of the largest tulip gardens in the country with over 850 varieties and 6 million tulips in bloom.

Lake Geneva, WI

Distance from Chicago: 82 miles via I-94W & WI-50 (1 hour 30 minutes)

If you’re looking for a beautiful and relaxing spot to visit, you can’t go wrong with Lake Geneva, which is just 2 hours from Chicago. This charming Wisconsin lakeside town is known for its stunning views, clear blue waters, and friendly residents; no wonder it’s one of the best midwest lake vacation destinations!

Here are some things to do on your next visit:

  1. Take a scenic stroll or bike ride around the Lakeshore Path. Lined with jaw-dropping mansions, there’s no better way to take in the beauty of Lake Geneva than by getting out by the water. Several miles of trails wind around the lake, making it perfect for a leisurely stroll, an invigorating run, or a bike ride.
  2. Visit one of the area’s wineries. The Lake Geneva region is home to several excellent wineries. You can tour the facilities, taste some of the wines, and learn about the wine-making process.
  3. Visit downtown Lake Geneva, full of charming shops and restaurants. Don’t forget to check out the iconic Riviera Water Fountain, a New York City Angel of the Waters Fountain replica.
  4. Get your adrenaline going at the Adventure Center at Grand Geneva. This family-friendly spot offers a variety of activities, including mountain biking, archery and disc golf.

More Tips For Your Family Road Trip

  • Crossing into Michigan? Remember you’re changing time zones; Michigan is an hour ahead on EDT (ESDT), while Illinois is on CDT (CSDT).
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