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What Are The Top 21 Day Trips From Chicago In 2024

Welcome to the Windy City! Whether you’re a local or a traveler looking to explore the skyline beyond the skyline, our guide to the best day trips from Chicago is your ticket to adventure. In a day’s drive from Chicago, we’ll show you how you can transform the city streets with scenic excursions. From charming small towns to natural wonders, get ready to discover the Midwest’s most unforgettable experiences. Pack your sense of adventure and hit the road – Chicago-style day trips await!

Incredible Day Trips from Chicago

In this travel guide, we give you ideas for the best day trips from the United States’ third largest city. Many places are located on the shores of Lake Michigan, taking you away from the city center. After exploring all the great things to do in Chicago, from the Chicago River to historic landmarks, head to these amazing spots that are easily accessible from the city.

The city is ideally located and offers easy border crossing to Wisconsin, Michigan and Indiana. It’s also a great base for a day trip further south to central Illinois. With four states at your fingertips, be sure to make time for a day trip during your visit.

1. Milwaukee, WI

What Are The Top 21 Day Trips From Chicago In 2024

Milwaukee is a big deal. This major city is located on the western shore of Lake Michigan in Wisconsin; It’s just 1.5 hours north of Chicago by train or car. Since Milwaukee is known for its breweries, we recommend taking the train if possible. Brewery tours are one of the best things to do in Milwaukee. Besides alcohol, there’s Holler House and the Milwaukee Art Museum. Don’t forget the Harley-Davidson Museum, which houses a beautiful motorcycle exhibit and documents iconic biker culture. The Milwaukee Public Museum also includes a large European village.

If you want a great day trip from Chicago, Milwaukee is ideal. It has a strong sense of culture and many interesting niches, such as Harley-Davidson motorcycles and breweries. You can also easily travel by train or car.

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

2. South Bend, IN

Day Trips from Chicago South Bend IL

South Bend, St. As a university town on the banks of the St. Joseph River, it has a different atmosphere. Great if you’re looking for a quieter city experience. You can visit the University of Notre Dame campus, famous for its classic golden domed building. You can also experience plenty of local history downtown, including auto manufacturing past at the Studebaker National Museum and regional history at the History Museum.

South Bend is definitely slower than fast Chicago. But it also has many attractions. Think of it as a relaxing and intellectual place to spend a day of sightseeing. There are many fun and student-friendly features, such as cheap bars and coffeehouses.

The city is located east of Chicago, across from Indiana Dunes National Park and on the lower east shore of Lake Michigan. It’s best to reach by car and we recommend stopping by the national park along the way.

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

3. Madison, WI

Day Trips from Chicago Madison IL

Little Madison may not look like a capital, but it’s actually the capital of Wisconsin, not the big, sprawling behemoth Milwaukee. This small city has a lot of beautiful architecture to offer. You can approach the historic Wisconsin State Capitol with its dome and walk the Capital City State Trail to see a variety of city attractions. Olbrich Botanical Gardens also offers a botanical garden experience, as well as a more stylish city center area with bars and cafés. If you’re looking for a political day trip from Chicago, Madison is your best option.

Madison also has a beautiful location on two large lakes (Lake Mendota and Lake Waubesa). Summer offers plenty of opportunities for water sports and sunny coastal hiking trails. Follow this walking tour to see the city’s architecture, including the State Capitol, Rathskaller, Bascomb Hill, and Memorial Flour

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

4. Starved Rock State Park, IL

Day Trips from Chicago Starved Rock State Park IL

Starved Rock State Park is one of Illinois’ most popular tourist attractions. Located on the banks of the Illinois River, the park is home to a collection of sandstone canyons surrounded by beautiful forests. The gorges were originally formed by melting glaciers, and you can explore the landscape via a network of clearly marked boardwalks. Starved Rock State Park is also home to numerous waterfalls that become impressively powerful during the rainy months.

Nature lovers will love this day trip. Not only is the natural scenery breathtaking, but you can also spot wildlife like white-tailed deer and bald eagles. Starved Rock State Park covers more than 2,600 acres and has 13 miles of hiking trails and 18 canyons to admire. It is located inland from Chicago and Lake Michigan.

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

5. Cedarburg, WI

What Are The Top 21 Day Trips From Chicago In 2024

Cedarburg has real charm. It features old-style houses and is often compared to a movie set. The city was founded in the 1840s by a mixture of predominantly Irish and German settlers and is now considered a suburb of Milwaukee. Cedarburg offers many fun and aesthetic opportunities, including brewery and winery tours. You can walk vineyards, tour breweries, or visit unique attractions like the Wisconsin Quilt and Fine Arts Museum. A true gem, Cedarburg moves to its own rhythm, making it a memorable day trip from Chicago.

This Wisconsin city is located north of downtown Milwaukee. The best way to get here from Chicago is by car, and you can always plan a stop in downtown Milwaukee – you can park and drive to the edge of town.

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

6. Illinois Beach State Park, IL

Day Trips from Chicago Illinois Beach State Park IL

If you’re looking for a beach, Illinois Beach State Park is the place to visit for a day trip from Chicago. The park covers more than 4,000 acres and has a beautiful network of riverside trails and hiking trails. It’s the ideal spot for a day at the beach on Lake Michigan. But Illinois Beach State Park is much more than a beach destination.

In addition to campsites and playgrounds, there are also shower blocks and a nature centre. You can spend the whole day at Illinois Beach State Park. Start with a hike and visit the nature center before heading to Isherwood Beach and even camping overnight if your schedule allows.

The park is very close to Chicago and can be reached by car in less than an hour. It’s a great day trip if you’ve had a hot day or want to go on a beach trip. Or if you want to take a break from your classic city break and go camping for a night, it’s the perfect adventure.

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

7. Lake Geneva, WI

Day Trips from Chicago Lake Geneva WI

Lake Geneva is a beautiful resort town on the shores of Lake Geneva in Wisconsin, northwest of Chicago. Since it is a small town outside of major public transport, it is best to reach by car.

As soon as you arrive, you will be greeted by Gilded Age mansions with impressive architecture and a scenic coastal path surrounding the Lake Geneva section of the city. Historically, Lake Geneva was used as a haven for Chicago’s wealthy residents, and when you look at the natural beauty of the city’s surroundings, it’s easy to see why.

Admire Victorian and Gilded Age architecture and visit the beaches of Lake Geneva. Big Foot Beach State Park has gorgeous beaches for a particularly relaxing afternoon. Lake Geneva is a nice day trip destination to relax before rediscovering Chicago’s chaotic travel scene.

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

8. Rockford, IL

Day Trips from Chicago Rockford IL

Rockford is a large city on the banks of the Mississippi, which is why it is called the “River City.” Rockford is also known as the “Forest City” because of its history of logging, forests and furniture industry. He is a shapeshifter with a long history and an important place in Illinois society. But today it is an ideal candidate for day trips and is full of popular tourist attractions and historical sites. You can visit the koi-filled ponds at Anderson Japanese Gardens, relax in one of the many public parks, or visit the Rockford Museum of Art. Tinker Swiss Cottage Museum and Gardens is also magnificent.

Rockford is located in northern Illinois, just below the Wisconsin border. We recommend combining this with a trip to Madison, about an hour uptown. A great stop for those heading to Wisconsin’s capital.

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

9. Indiana Dunes National Park, IN

Day Trips from Chicago Indiana Dunes National Park IN

If you love the beauty of nature, forget state parks; Go big with Indiana Dunes National Park. More than just sand dunes, this stunning park stretches over 24 kilometers of beautiful coastline, perfect for swimming and sunbathing. Indiana Dunes National Park is also a popular spot for bird watching and hiking. The national park is located at the southern end of Lake Michigan. It is a beautiful place to visit to enjoy the beauty of the lake. The entrance ticket costs around $20 and you can spend the whole day exploring the park.

Indiana Dunes National Park is located southeast of Chicago and can be ideally combined with visits to South Bend or day trips to Michigan or Indiana.

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

10. Lakeshore State Park, WI

Day Trips from Chicago Lakeshore State Park WI

Everyone loves the city park. This magnificent park is located on the Milwaukee waterfront. But we’ll include it as an attraction in its own right, as it deserves a visit on its own. The best way to explore Lakeshore State Park is to walk along the Hank Aaron State Trail. Enjoy expansive views of the city skyline and Lake Michigan. If you’re looking for a romantic day trip from Chicago, head to Lakeshore State Park for a sunset picnic.

The state park can of course be easily combined with a visit to Milwaukee. This little Island State Park is a beautiful spot close to town. It is located away from the historic third district and is accessible from the mainland via a pedestrian bridge.

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

11. Monroe, WI

What Are The Top 21 Day Trips From Chicago In 2024

Monroe is pretty cool. The quaint town is known as the cheese capital of Switzerland. It has a long history in dairy farming, which has earned it an excellent reputation for cheese. You can take part in highly recommended food tours and taste local products. Be sure to visit the National Historic Cheesemaking Center Museum and the Chalet Cheese Cooperative. There are also beautiful architectural and historical landmarks, such as the Green County Courthouse, completed in 1891. Monroe Historic Square is located in the city center, surrounded by shops and aesthetic landscaping.

Compared to some of Chicago’s neighboring larger cities, Monroe is a small city. It is about half the size of Madison and Rockford. It’s definitely best to reach by car.

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

12. St. Joseph, MI

Day Trips from Chicago St Joseph MI

St Joseph , a picturesque seaside town in southwestern Michigan. St. Joseph is an ideal day trip if you want to take a day trip from Chicago to Michigan. Located on the shores of Lake Michigan, it features beautiful attractions such as Silver Beach County Park and Lions Park Beach. Particularly worth a visit is Silver Beach, which has a 1910 carousel and restored pavilion, giving the town a wonderful vintage aesthetic. A classic red-and-white lighthouse stands near the city’s north pier.

If you want to join one of the traditional seaside day trips, visit St. Joseph is a great choice. Even though you pass through Indiana and cross the Michigan border, it’s a short drive from Chicago. Cheers to the close network of US states on Lake Michigan. It combines fantastically with Indiana Dunes National Park and Michigan City.

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

13. Channahon State Park, IL

Day Trips from Channahon State Park IL

Channahon State Park is an absolute must. Located on the edge of some of Illinois’ most historic canals, the state park is home to a restored lock tender house of special historic value. You can enjoy the network of hiking trails with waterfalls, birds and historical paths where you can take photos. Distance is not an issue when visiting interior Illinois; Channahon State Park is less than an hour’s drive from downtown Chicago. A great day trip if you want minimal travel time and a look at Illinois’ canal history.

You can take guided tours around Channahon State Park, including canoe trips. The state park is a designated part of the Illinois and Michigan Canal National Heritage Corridor. It is widely celebrated as an integral part of the state’s history. It is an adventure park created by nature.

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

14. Oak Park, IL

Day Trips from chicago Oak Park IL

Oak Park is a beautiful village in the suburbs of Chicago. For such a small space it is truly an achievement that goes beyond beautiful architecture. Visitors can enjoy attractions such as the Frank Lloyd Wright Home and Studio, Ernest Hemingway’s Boyhood Home, Mills Park National Historic Landmark, and the Oak Park River Forest Museum. Oak Park is a quick selection of museums in a small area accessible by public transportation from downtown Chicago. What is not love? It’s the perfect choice if you want a hassle-free trip from Chicago.

It is so easy to get on the train and be among dozens of museums. Additionally, the Temple of Unity was recently declared a UNESCO World Heritage Site in 2019. Despite all the attractions and amenities available, Oak Park is on the rise in terms of visitor awareness and tourism value.

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

15. Grand Rapids, MI

Day Trips from chicago Grand Rapids MI

Grand Rapids is another big city; Think of a beautiful riverscape full of skyscrapers and stunning bridges. Grand Rapids has a lot of culture to offer through museums like the Gerald Ford Presidential Museum and the Grand Rapids Public Museum. There’s also a great, safe, walkable area downtown that includes the Grand Rapids Museum of Art, an attraction and initiative that highlights local artists.

We love taking shuttles to Grand Rapids because it has a glorious brewing history. It is especially known for New Holland Brewing, and you can take guided tasting tours of local breweries that are still in operation. Otherwise the drive is faster and includes Indiana Sand Dunes National Park, St. You can stop in places like St. Joseph and South Bend. They hug the lower shore of Lake Michigan, a long but very scenic journey. Ideally, you will change drivers and make a few stops along the way.

  • Distance from Chicago: 3 to 5 hours
  • How to get there: By car in just under 3 hours or by shuttle in under 4

16. Windmill Island Gardens, MI

Day Trips from chicago Windmill Island Gardens MI

Chicago may be known as the Windy City, but check out Windmill Island Gardens. This seasonal park features a 250-year-old windmill as a nod to the city’s Dutch influence. You can take self-guided tours of the park, admire the windmill, and meet guides wearing traditional Dutch costumes. There is also a tulip garden that is dazzling in spring.

If you want to enjoy Dutch heritage, this is one of the most popular day trips from Chicago, and it even takes in a city called Holland. Since Windmill Island Gardens is in Michigan, you’ll travel along the southern shore of Lake Michigan, through northern Indiana, and along the Michigan border. Distance can be an issue when visiting Michigan. Long day of driving? Yes. But it’s incredibly picturesque and a great way to combine various attractions. If you have more than one driver, you won’t have any problems as you can easily change driving times.

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

17. Galena, IL

Day Trips from chicago Galena IL

Galena is an absolute gem of a charming little town on the Galena River with lots of Civil War history. The city was the home of Civil War General Ulysses S. Grant, and its former home is a state historic site. Of course, Ulysses S. Grant later became President of the United States, so his story has been immortalized. Galena is a great place to visit if you are interested in politics and history. The city center is relatively walkable and full of history and picturesque 19th-century architecture.

Galena is located in the upper left corner of Illinois, on the Iowa-Wisconsin border. It’s a great addition to Rockford or Starved Rock State Park, which is about an hour and a half drive away.

18. Michigan City, IN

Day Trips from chicago Michigan City IN

Michigan City is just an hour away, offering a perfect, easily accessible destination. If you’re looking for a one-way trip from Chicago, Michigan City is for you. Do you want to go for a ride? You can get there within an hour by car, passing Indiana Dunes National Park. How about a train journey? You can read a book or take a nap and reach the city in less than 2 hours. There’s plenty of culture and history along the lakefront, with many lighthouses to admire and picturesque Washington Park Beach.

Historic history also abounds at Barker Mansion, which showcases English-inspired decorations and furnishings in a 19th-century mansion. Marvel at history, spend a day at the beach, or enjoy shopping at the outlet stores downtown. Michigan City offers a lot, and at least it’s a change.

You can easily visit Michigan City; Convenient day trips have little travel time and lots of attractions. That pretty much sums up the lakeside town.

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

19. Peoria, IL

Day Trips from chicago Peoria IL

Michigan City is just an hour away, offering a perfect, easily accessible destination. If you’re looking for an easy trip from Chicago, Michigan City is for you. Do you want to go for a ride? You can get there with an hour’s drive past Indiana Dunes National Park. How about a train journey? You can read a book or take a nap and reach the city in less than 2 hours. There is a lot of culture and history along the lakeshore, with many lighthouses to admire and the picturesque Washington Park Beach.

Barker Manor is also steeped in history, showcasing English-inspired decorations and furnishings in a 19th-century mansion. Marvel at history, spend a day at the beach, or enjoy shopping at the outlet stores downtown. Michigan City offers a lot, and at least it’s a change.

You can easily visit Michigan City; Decent day trips have little travel time and lots of attractions. That pretty much sums up the lakeside city.

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

20. Six Flags Great America, IL

Day Trips from chicago Six Flags Great America IL

What about a day at an amusement park? Six Flags Great America is a chain of amusement parks scattered across the US. And there is one on the outskirts of Chicago, creating the best day trip for fun-loving tourists. The park has water park rides, rollercoasters, and all-round fun entertainment. You can get adrenaline on rides like Sky Striker or the American Eagle. Alternatively, try the sedate, family-friendly rides like the Big Easy Balloons or Cubasco tea cups.

Everyone loves a fun day out. And Six Flags Great America is the perfect day trip to skip sightseeing and escape the city to enjoy some quality ‘fun’ time. It is the ideal place to let your hair down and has an impressive range of rides, making it suitable for adults and children. Six Flags Great America is located north of Chicago, just under the Wisconsin border.

  • 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

Day Trips from chicago Glacial Park Conservation Area

Finally, there is the beautiful Glacial Park Preserve. This 3,400-acre preserve is a stunning mix of wetlands and grasslands with glacial ridges and numerous natural opportunities for canoeing or fishing. It is one of the most photogenic places where you can experience the beauty of nature on a day trip from Chicago. You can explore Glacial Park on foot or by boat, or switch things up and book a horseback riding tour. The park has a total of 8 miles of shared trails, and you’ll definitely want to bring a camera.

Glacial Park Preserve is open year-round from sunrise to sunset. Ideal if you want to switch from the usual suburban park experience to something more rugged and remote.

  • Distance from Chicago: 1 hour and 20 minutes
  • How to get there: By car
What Are The Top 21 Day Trips From Chicago In 2024

Whether it’s Dutch heritage, rich Civil War history, or rides at Six Flags America water park, there’s so much to experience on your day trip from Chicago. Enjoy the small-town charm of Oglesby, the natural beauty and wonder of Indiana Dunes National Park, or enjoy craft beers at a local brewery. Chicago’s location on the border with three other states means you have a lot of variety when choosing day trips. And the constant presence of beautiful Lake Michigan means a constant stream of water sports and beaches. I hope you have at least 5 or 6 day trip options.

Looking for more inspiration? Check out our guides to the best things to do in Wisconsin and the best things to see in Michigan. We’ve also put together tips on the best and most unique things to do specifically in Northern Michigan. If you have time to squeeze in a few more days at the end of your Chicago trip, check these out. If you have longer time, why not take a 2-3 day trip from Chicago? It’s a great base to explore more experiences in the states surrounding Lake Michigan. Chicago’s location is by far its plus point and you should take advantage of this when planning day trips and excursions.

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Daniyal is an accomplished travel blogger boasting two years of extensive experience. Proficient in captivating narratives, Daniyal unveils the allure of undiscovered destinations and divulges insights into everything regarding traveling. Beyond the prose, he serves as the editorial architect, seamlessly incorporating editing finesse, SEO mastery, and strategic content deployment to ensure a sophisticated and enriching online travel experience.
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