20 Best Day Trips From Chicago, Illinois

Uncover the gems beyond the Windy City with these day trips from Chicago, Illinois. Each location, easily reachable within a day’s journey, promises unique attractions and memorable experiences.

Even though Chicago has a lot to offer, such as the Willis Tower and the Navy Pier, sometimes a getaway is refreshing. Fortunately, Chicago falls close to many explorable spots: small towns, dynamic cities, National Parks, gorgeous lakeshores, and more.

In this guide, we’ll discuss some of these places you can visit for your day trips from Chicago. Once you’re done exploring Chicago with your CityPass, it’s time to head further.

In this guide, we’ve tried sticking to family-friendly day trips from the Chicago area so you can take your kids and pets along for the ride. Let’s explore what wonders lie close to the beautiful city of Chicago.

Day Trips From Chicago, Illinois 

1. Indiana Dunes National Park

Indiana Dunes National Park is only about 40 miles from Chicago down I-90 and is a stunning experience. It’s easily one of the best national parks in the Midwest. Over millions of years, the waves and winds coming off Lake Michigan have helped to shape these dunes, creating more than 15 miles of impressive coastline to explore.

Fishing, boating, and stargazing are a few ways to spend your time. There are historical sites to explore, too, including the 60 structures that are part of the National Historic Landmark called Bailly Homestead.

When visiting here on a road trip, plan to spend some time hiking or horseback riding through the area. Many spend a weekend trip in this area to enjoy the 15 miles of beaches.

There’s something special about the Lake Michigan sunset. Explore Lake Michigan’s Southern Shore on a kayak for a bit of a challenge or relax in the water off the shore.

2. South Bend, Indiana

South Bend is a modern city about 95 miles west of Chicago with much to offer. It is one of the best Midwest road trips for those who love a bit of sports history, thanks to the College Football Hall of Fame and the University of Notre Dame itself.

There’s much more to explore here, including touring the Studebaker National Museum and the Basilica of the Sacred Heart with its 125 years of history. Take in a show at the Morris Performing Arts Center, noted for its beautiful architecture and history as a vaudeville performance hall.

You can have some fun outside, too, including going whitewater rafting, ice skating during the winter months, and making a trip to the Potawatomi Zoo. You can always get freshly made local cuisine or shop at South Benefit Farmer’s Market. The Indiana Whiskey Company also has some fantastic brews on tap throughout the year.

3. Michigan City, Indiana

Michigan City is an excellent day trip for those who want to stay close to Lake Michigan (you can even see the towering Chicago skyline from here). It’s about 60 miles to the east, right along the shoreline. Located on Lake Michigan’s Southern Shore, it’s a beautiful place to visit from sunrise to sunset.

You can tour the Old Lighthouse Museum while here and check out the region’s historic shipwrecks (and the stories of those ill-fated trips).

Some come to spend time at Washington Park Zoo, where the wolves and alligator displays are noted for their conservation and focus on educational support. Be sure to check out Friendship Botanic Gardens on a spring day or fall afternoon for impressively beautiful nature.

Washington Park has a fun outdoor vibe, with a beach area and a rock garden to explore. Michigan City offers plenty of things to do, including the Blue Chip Casino and Spa and Lighthouse Place Premium Outlets, the perfect location for some retail therapy.

4. Evanston, Illinois

Here’s a short-day trip option. Evanston to Chicago is only about 15 miles, but it is well worth a day from start to finish. A fantastic, moderately sized community on the North Shore of the lake, it is noted as the home of Northwestern University.

However, there’s more to do and see here, including exploring Grosse Point Lighthouse, a historical mansion with exceptional architecture, and checking out the music lineup at Evanston SPACE.

When in Evanston during the spring and summer, check out the Merrick Rose Garden and the Evanston History Center, both of which offer tours by in-house staff. You can take in a bit of history in the Shakespeare Garden or Frances Willard House Museum. There’s also a waterfront to Evanston, making it possible to head out on a boat ride to Chicago, if you’d like.

See Related: Things to Do on the Magnificent Mile

5. Lake Geneva, Wisconsin

You might have Lake Michigan in the city, but Lake Geneva offers a whole experience. The lake is more like a resort city, offering multiple options for fun and scenic views. 

In the Gilded Age, wealthy people from Chicago came to build grand houses on Lake Geneva for their summer hideaways. It’s a popular tourist spot, attracting thousands yearly for its beauty and unparalleled summer weekends.

Since it’s also a year-round spot, you can go whenever you feel like getting away from the hustle and bustle of Chicago. The best thing to do at Lake Geneva is to walk or bike along the shoreline. It’s a 21-mile shoreline that lets you take in the beautiful views of the natural beauty.

Depending on the season, there is enjoyable nightlife, shops, restaurants, and many outdoor activities. If you fall in love with the lake, you can even book a cozy vacation rental on VRBO in the area and wake up to the view of Lake Geneva the next day. 

6. Milwaukee, Wisconsin

Just an hour and a half drive from Chicago, Milwaukee is known for its beer. But that’s not the only thing that makes it one of the most fascinating cities near Chicago.

Although the city still boasts its brewing heritage, there’s much more to do. For instance, you can go on brewery tours to understand the history behind the city’s central business. Plus, you’ll find many farm-to-table restaurants serving made beer. 

While it may initially seem so, not all activities in the city are centered around beer. Milwaukee is also famous for being the cultural representative of Harley-Davidson. If you love bikes or have a family member who does, this is a much-needed getaway for you. 

You can visit the local museum with many artifacts, including the oldest ever Harley. Speaking of old, Milwaukee also seems to love its traditions. The city is often called the City of Festivals. 

With more than 12 annual celebrations, you’ll probably catch one on your day trip. Don’t forget to leverage sites like Booking for deals on accommodation if you’re too tired to go home after the celebrations.

If you’re in the city for an extra day, visit one of the 150 parks in the area or try to enjoy a game at one of the city’s 75 golf courses near Chicago. If you’re a film fan, Milwaukee also has 25 theatres, serving you entertainment on a platter.

In short, it’s one of the best day trips from Chicago. If you’re traveling with pets or with kids, I’d bump this to the top of your list.

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7. Starved Rock State Park, Illinois

Starved Rock State Park, an enticing haven of natural splendor, is tucked away along the Illinois River in North Central Illinois. Its proximity to Chicago makes it an ideal day trip for those seeking a respite from the city.

The park is a portal to many outdoor adventures, catering to everyone from seasoned adventurers to those who enjoy the peacefulness of nature. With over 13 miles of hiking trails, the park beckons visitors to journey through its landscapes that shift with the seasons.

Secret waterfalls nestled within sandstone canyons, verdant forests brimming with wildlife, and sweeping views of the Illinois River are some of the park’s most mesmerizing features. The river is a hub for fishing, boating, and even spotting eagles during winter.

Starved Rock State Park is steeped in history as well. The intriguing name of the park stems from a Native American tale of injustice and vengeance, adding a touch of mystery to this natural wonder. A visitor center provides a glimpse into the area’s bygone era, ensuring history buffs will find their visit rewarding.

8. St. Joseph, Michigan 

St. Joseph is also just an hour’s ride from downtown Chicago. Once you’re there, the city is famous for holding a huge multi-community festival, and it’s one of the oldest in Michigan. 

The Blossomtime Festival marks the blooming of orchards every year in the most exciting way you could imagine – vintage baseball is just the start. There’s a parade

 If you’re an art lover, you should head to Box Factory for the Arts, a tory-turned-gallery showing the works of more than 40 artists. The Krasl Art Center is another must-visit place that features sculptures and other art in three galleries. 

Sometimes, it can be hard to keep the kids occupied on day trips, but that’s not the case with St. Joseph. It has a Curious Kids’ Museum where your little ones can be ambulance drivers for the day, blow giant bubbles, or be amused by the many onsite exhibits. 

Another place to take the kids is Silver Beach Country Park, which offers water activities along with amusement rides. The carousel will offer a lot of entertainment for you and your kids. 

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9. Woodstock, Illinois 

It wouldn’t be right not to mention Woodstock when discussing day trips from Chicago. Most people would recognize the town from the Bill Murray classic film Groundhog Day. That should give you an idea that you’re in for a cinematic treat in Woodstock. 

While most people debate the authenticity of books over movies, Woodstock seems to love both. The town has a bookshop called Read Between the Lynes, where you can enjoy interesting book-ish treats while playing quirky yet fun games. 

Moreover, the town also has a Farmer’s Market from May to October. If you visit on a Saturday or Tuesday, you can see the markets to socialize with the farmers and locals. 

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10. Kettle Moraine State Park

If you’re looking for state parks near Chicago, the Kettle Moraine State Park should be the first on your list. The park was formed millennials ago by the melting of glaciers and the formation of depressions. 

Today, it is a delightful tourist spot with multiple activities, from hiking to swimming. Since the Kettle Moraine South section is nearest to Chicago, you can head there for the day to enjoy the flower fields and forests. 

Even better, if you want to stay the night, you won’t have to look for campgrounds near Chicago, as the park has three of its own. Or, you benefit from an RV rental on RVshare and take your accommodation along. 

See Related: Chicago vs. Detroit

11. Madison, Wisconsin

Located 145 miles west of Chicago, Madison, as the capital city of Wisconsin, is noted for numerous amenities, including the beautifully domed Wisconsin State Capitol Building.

Regarding road trips from Chicago for outdoor lovers, that’s easy to do here, thanks to the Henry Vilas Zoo and Olbrich Botanical Gardens, noteworthy locations with outstanding exhibits. It’s also one of the most bike-friendly cities with miles of trails (you can hike them, too!)

The city is also noted for its numerous museums and cultural events, including several music venues. It’s home to the Wisconsin Historical Museum, UW Geology Museum (with its huge fossil collection), and the Madison Masonic Center, a noted landmark with historical memorabilia. 

Consider a show at the Overture Center for the Arts or American Players Theater for things to do in Madison. And, with dozens of restaurants in Madison, it’s undoubtedly a full-day experience.

12. Naperville 

Naperville is one of the shortest day trips from Chicago, less than an hour away from the city. Besides its small-town charm, Naperville is also known for its many accolades. Money Magazine named it one of the best places to live.

Moreover, it has also been declared one of the best five kid-friendly cities in the country. So, if you’re planning day trips from Chicago with pets or kids, you know where to go. 

Naperville’s Riverwalk is one of the best attractions in the region, spanning beside the DuPage River for 1.75 miles. You’ll also enjoy the sight of a clock tower, a bell tower, a covered bridge, three fountains, and many sculptures that show the city’s heritage. 

If you get hungry, head to the Centennial Beach and Grill, an amalgamation of a beach waterpark and an eatery. Overall, it makes one of the best fall day trips from Chicago. 

13. Six Flags Great America

While hiking or outdoorsy day trips from Chicago aren’t always possible with the kids’ school schedules, you can take them to an amusement park instead. Six Flags America is one of the most popular amusement parks nationally for all the right reasons. 

It has 17 kid-specific, 24 family-friendly, and 17 thrill rides – just what you need to turn a boring weekend around. When your stomach starts rumbling, you can walk to one of the 50-plus eateries and food stands to fulfill your cravings. We suggest doing that after you come off the rides, though. 

Along with the rides, the park also offers other forms of entertainment, such as Hurricane Harbor, a water park featuring thirty attractions. Some include water playgrounds for children, water slides, and surf simulators. 

If you’d like to turn this into a family hangout, chill at the 14,000-square-foot pool designated for families. Most importantly, the amusement park is only an hour from Chicago, so you won’t be behind the wheel long. 

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14. Village of Oak Park

If you prefer less happening and more calming day trips from Chicago, don’t forget to visit the Village of Oak Park, just 15 minutes away from the city. 

One of the most exciting things about Oak Park is its diversity. The local community is a hub of racial, religious, socio-economic, and ethnic diversity. To put it in simpler words, you’re welcome in the village irrespective of your social status, ethnicity, race, color, or profession. 

If you’re into history and architecture, you might want to go to Wright District. Your walking tour of the area will allow you to marvel at Frank Lloyd-designed homes. 

Moreover, you can visit his studio and home. As for the kids, they’d like to spend the day at the Brookfield Zoo. It also won’t be wrong to say that this is among the best fall trips from Chicago because the village has a lot of scenic value. 

See Related: Things to Do in Rockford, Illinois

15. Holland, Michigan

Make the 150-mile trip to Holland, Michigan, if you’re looking for another option for a weekend trip out of the Windy City. You’ll find a vibrant community that feels much like Holland itself.

It’s located on the shore of Lake Macatawa, which gives you lots of access to beachfront property, fishing, swimming, and stunning sunrise views in the morning. You can see the Big Red Lighthouse, where Lake Macatawa links to Lake Michigan.

Plan to be busy in Holland, whether biking along the paved paths near the waterfront or touring the Windmill Island Gardens. You can take in the Nelis’ Dutch Village, an amusement park with fun food and entertainment.

The Outdoor Discovery Center is an excellent way to explore a nature preserve, while the Windows on the Waterfront allows for a day of on-the-beach fun. It’s a bigger city with all the small-town charm you want on a road trip.

16. North Utica 

If you love everything to do with nature, rustic shops, and antique stores, this is one of the best day trips from Chicago. Situated close to the Illinois River, North Utica is a small town that appeals to people who love nature. 

The town has everything from flea markets and collectible shops to wine shops and a pottery studio. You won’t be short of things to do. If you want to dive deeper into the history of North Utica, you can head over to the LaSalle County Historical Museum. 

The town also offers fine dining at places like the Cajun Connection. If you plan on spending the whole day here, get a day pass from the Grand Bear Resort. You’ll get access to their sports bar, restaurant, sweet shop, and indoor waterpark.  If you want to explore one of the four state parks near North Utica, search for a hotel on Booking.com to stay the night in the area. 

See Related: Day Trips from Des Moines

17. Oglesby 

If North Utica isn’t your cup of tea, here’s another river town falling where the Vermillion River and Illinois River meet. Blessed with scenic landscapes, the city is a popular spot for day trips from Chicago since it offers much. If you’re interested in the state parks near Chicago, explore the Starved Rock State Park or the Matthiessen State Park. 

Other outdoor activities include hiking, canoeing, horseback riding, and kayaking. You don’t even have to look for golf courses near Chicago, as the town has those, too. By is undoubtedly on our list of the best hiking day trips from Chicago. 

There’s a Santa’s Holiday Open House in December with many activities and fun carriage rides. If you plan to spend the night, search for accommodation on Booking.com. You might bet a discount on your American Express Platinum card rewards. 

If you visit the town in October, you can turn it into one of the best winter day trips from Chicago by going to the Harvest Fest. It takes place in mid-October and has a lot of activities for kids and adults alike. 

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18. Chicago Botanic Garden

Here’s one of the day trips from Chicago close to home. This is the best place if you enjoy nature and want to spend the day amidst well-manicured lawns and flowerbeds. 

The easiest way to explore the garden is by downloading their app. It will take you on a walking tour of the park. If you’re bringing kids along, take them to the Nature Play Garden. Here, they can explore the flora of the region.

Additionally, you can take birding classes and buy souvenirs from the gift shop. Plus, you can rent a bike or enjoy lunch at the onsite restaurant. 

See Related: Chicago CityPASS Review

19. Grand Rapids, Michigan

Grand Rapids is a large city that makes for the perfect weekend trip. It’s about 180 miles or about 3 hours from Chicago. Start with spending some time on the Grand River, which runs along the east of the lake. There are plenty of great things to do in Grand Rapids in a short period or a quick getaway.

Take in the area’s best museums, including the Grand Rapids Public Museum and Frederik Meijer Gardens & Sculpture Park (perfect on a cool day). You can also take a haunted walking tour with a guide if you need an adventure.

Explore the city’s natural areas, including the Blandford Nature Center, a natural preserve with a boardwalk to explore the various habitats. Another option is to shop at the Grand Rapids Downtown Market and Fulton Street Market (for a true farmer’s market experience).

Stop in for a drink at the Founders Brewing Co. or Brewery Vinant, which are excellent choices for local craft brews. Bring the whole family to the Grand Rapids Children’s Museum that’s nearby, too. Given the number of activities, it might be better suited for a weekend road trip to see all that the city has to offer.

20. Four Lakes Alpine Snowsports

The Four Lakes Alpine Snowsports is located in Illinois for people interested in skiing near Chicago. It is just over half an hour’s drive away from the city. 

Although it’s a smaller complex compared to many others that are a bit farther from Chicago, it offers different trails to keep you occupied for the day. To make it one of your best winter day trips from the Chicago area, you can take a skiing lesson or rent gear if you’re already a pro. 

Another similar area for skiing near Chicago is Tilla Olivia. It is 45 minutes away and also has a chairlift. You can make a romantic day trip with your partner even better by spending the night at the Marriott Downtown Magnificent Mile. 

Related Resources

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