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12 Best Day Trips From Chicago, Illinois

Looking for the best day trips from Chicago to travel to and from within 24 hours? If yes, I have listed the 12 best day trip options for you.

Even though Chicago has a lot to offer, such as the Willis Tower and the Navy Pier, sometimes, a getaway is refreshing.

Fortunately, being at the heart of the country, Chicago falls close to many explorable spots, ranging from beaten tracks and small towns to national parks and lakes. 

Chicago Skyline Summer

In this guide, we’ll discuss some of these places that you can visit for your day trips from Chicago. 

Whether you’re looking for state parks near Chicago or golf courses where you can enjoy the greens, you’ll find it all in this article. 

Best Day Trips From Chicago Area 

Once you’re done exploring Chicago with your CityPass, it’s time to head further. We’ve tried sticking to family-friendly day trips from the Chicago area in this guide, Therefore, you can take your kids and pets along for the ride too. 

Let’s explore what wonders lie in the close distance of your beautiful city

Lake Geneva

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

Lake Geneva, Wisconsin

In the Gilded Age, the wealthy people from Chicago used to come here to build their grand houses. Now, it’s a popular tourist spot, attracting thousands of visitors every year for its sheer beauty and grandeur. 

Since it’s a year-round spot, you can go whenever you feel like getting away from the hustle and bustle of the Chicago city.

The best thing to do at Lake Geneva is to walk along the shoreline. It’s a 21-mile shoreline that lets you take in the beautiful views of the natural beauty.

You can also bike on the path. 

Additionally, the resort offers other activities. These include enjoyable nightlife, shops, restaurants, and lots of outdoor activities, depending on the season. 

If you fall in love with the sight, you can even book a cozy Airbnb in the area and wake up to the view of Lake Geneva the next day. 


Just an hour and a half drive away 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 a lot more to do there too. 

Milwaukee Skyline

For instance, you can go on brewery tours to understand the history behind the city’s main business. Plus, you’ll find a ton of farm-to-table restaurants that serve locally-made beer. 

While it may initially seem so, not all activities in the city are centered around beer. Milwaukee is also popular 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 that has many artifacts, including the oldest ever Harley. 

Speaking of old, Milwaukee also seems to love its traditions. The city has many festivals throughout the year and is actually often called the City of Festivals. 

With more than 12 celebrations per year, you’re bound to catch one of them on your day trip. Don’t forget to leverage sites like Booking for accommodation if you’re too tired to go home after the celebrations.

If you’re in the city an extra day, be sure to 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 with pets and kids because there’s something for everyone. 

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St. Joseph, Michigan 

St. Joseph is also just over an hour’s ride from Chicago, but once you’re there, the ride will be worth it. The city is popular for holding one of the biggest multi-community festivals, which also happens to be one of the oldest in Michigan. 

St. Joseph, Michigan

The Blossomtime Festival marks the blooming of orchards every year in the most interesting way you could imagine – vintage baseball and a run are involved. 

If you’re an art lover, you should head over to the Box Factory for the Arts, which is a factory-turned-gallery, showing works of more than 40 artists. 

Moreover, the Krasl Art Center is another must-visit place that features sculptures and other arts in three galleries. 

Sometimes, it can be hard to keep the kids occupied when you go to cities near Chicago, 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 the 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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Woodstock, Illinois 

It wouldn’t be right not to mention Woodstock when talking about 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. 

Woodstock, Illinois

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’re visiting on a Saturday or Tuesday, you can visit the markets to socialize with the farmers and other locals. 

If you’re in the mood for some music and festivities, the Woodstock Folk Festival provides just that. Did you know that it was supposed to be a one-time thing? However, the people loved it so much that they managed to bring it back for every subsequent year since 1986. 

Mark your calendar for the third Sunday of July to enjoy the folk music at the event. 

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Kettle Moraine State Park

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

Kettle Moraine State Park

Today, it serves as an immensely enjoyable tourist spot with multiple activities, ranging from boating and 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 RVshare and take your accommodation along. 

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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. The Money Magazine named it as one of the best places to live.

Moreover, it has also been declared 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 1.75miles. You’ll also enjoy the sight of a clock tower, a bell tower, a cover bridge, three fountains, and many sculptures that show the heritage of the city. 

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

Six Flags Great America

While hiking 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 and for all the right reasons. 

Six Flags Great America

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 over 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, which is a water park featuring thirty attractions. Some of them include water playgrounds for children, water slides, and surf simulators. 

If you’d like to turn this into a family hangout, chill at the 14000 square-foot pool that’s designated for families.

Most importantly, the amusement park is only an hour away from Chicago, so you won’t be behind the wheel for long. 

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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, which is just 15 minutes away from the city. 

Village of Oak Park

One of the most interesting 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 to the area will allow you to marvel at Frank Lloyd-designed homes in the area. 

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: 16 Fun & Best Things to Do in Rockford, Illinois

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 for you. 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. Basically, 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 Kayak to stay the night in the area. 

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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 landscape, the town is a popular spot for day trips from Chicago since it has a lot to offer. 

If you’re interested in the state parks near Chicago, explore the Starved Rock State Park or the Matthiessen State Park. 

Alternatively, there are many other outdoor activities, such as fishing, hiking, canoeing, horseback riding, and kayaking. You don’t even have to look for golf courses near Chicago as the town has those too. 

Plus, Oglesby is surely on our list of the best hiking day trips from Chicago. 

Plus, there’s a Santa’s Holiday Open House in December that has a ton of festive activities and fun carriage rides. If you plan to spend the night, search for accommodation on Kayak. You might be able to get a discount on your American Express Platinum card rewards. 

If you’re visiting 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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Chicago Botanic Garden

Here’s one of the day trips from Chicago that’s close to home. If you enjoy nature and would want to spend the day amidst well-manicured lawns and flowerbeds, this is the best place for you. 

The easiest way to explore the garden is by downloading their app on your phone. It will take you on a walking tour of the garden. 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

Four Lakes Alpine Snowsports

For people who might be interested in skiing near Chicago, the Four Lakes Alpine is located in Illinois. 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 that will 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 the Villa 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

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