Overlooking view of Downtown Milwaukee during sunset

17 Day Trips from Chicago (By a Local!)

Looking for the best day trips from Chicago? Then you’ve come to the right place!

When it comes to cities, Chicago has it all: incredible architecture, access to Lake Michigan, and all the arts, culture, and attractions you could wish for. But every now and then, it feels good to escape the hustle and bustle and explore somewhere new. 

As a Chicago local, I can tell you that there are a ton of fun day trips from Chicago that are only within a few hours’ driving distance.

Whether you’re a midwestern local or just want to tack on a day trip to your visit to Chicago, I’ve got you covered with 17 destinations sure to give you that mini travel fix you’ve been craving. 

Oh, and be sure to also bookmark my guide to what to do in Chicago. Now, let’s get day tripping!

Disclosure: Travel Lemming is an independent reader-supported blog. You can support us by purchasing via the affiliate links on this page, which may earn us commissions. Thank you!

17 Best Chicago Day Trips

Milwaukee, WI

Relaxing view from the Riverwalk in Milwaukee
Enjoy a beer at one of the many breweries along Milwaukee’s famous RiverWalk

Distance from Chicago: 1.5 hours | Google Maps | Milwaukee Website | 👉 Top Milwaukee Tours

Located just an hour and a half north of Chicago, along the western shore of Lake Michigan, is Milwaukee, Wisconsin. This quintessential midwestern city is the perfect day trip for a city vibe with a slower pace. It has beautiful lakefront access and a RiverWalk that connects the city center to different neighborhoods that have a lot to offer.

One of the biggest things the city and region are known for is its thriving beer scene. For a true taste of Milwaukee, visit one of more than 30 breweries located throughout the city and surrounding areas. 

If beer isn’t your thing, then check out an impressive collection of art at the Milwaukee Art Museum, located along the lakefront. The Harley Davidson Museum is also a popular destination to learn about the history of the all-American motorcycle. 

Holland, MI

A field of colorful tulips in Holland and a windmill
Nothing says “Dutch” like a beautiful field of tulips

Distance from Chicago: 2.5 to 3 hours | Google Maps | Holland Website 

If you’ve been craving a European vacation, then look no further than Holland, Michigan. This small city on the eastern shores of Lake Michigan, nestled along Lake Macatawa, was settled by Dutch immigrants in 1847. Today, the town continues to celebrate that rich heritage.

Although Holland’s charming small-town feel is enough to make it a destination worth visiting, a huge attraction is the city’s Windmill Island Gardens. Here, you can transport yourself to the Netherlands and enjoy a walk around canals, a field of tulips, and an authentic Dutch windmill (open seasonally, April 18th – October 2nd, 2022). 

Holland is also a great destination for families. If you have younger kids, visit Nelis’ Dutch Village and let them experience a Netherlands all their own. The park features things like wooden shoe carving, rides, and a petting farm. 

If you plan on visiting in the springtime for the famous Tulip Time Festival, book ahead to avoid any hassle since this is a popular event (it runs from May 7th – 15th, 2022). If you plan on visiting any other time of year, don’t fret. Holland still has a lot to offer with great beaches, events, and a main street full of restaurants, shops, and breweries. 

🛏️ Need a Hotel? The Courtyard by Marriott Holland Downtown is a great option for where to stay in Chicago, since it’s within walking distance to downtown. 

Lake Geneva

View of the Lake Geneva during a sunny morning walk
Take a stroll on the Lake Geneva Shore Path to get a taste of the town’s history

Distance from Chicago: 1.5 hours | Google Maps | Lake Geneva Website | 👉 Top Suggested Tour

Just an hour and a half northwest of Chicago is the resort town of Lake Geneva. This family-friendly town sits along Geneva Lake and offers visitors a perfect balance of relaxation and outdoor activities. For some small-town charm, stroll around Lake Geneva’s downtown and enjoy great restaurants with plenty of local shops. 

The town also has a unique connection to Chicago history. After the Great Chicago Fire of 1871, lots of wealthy Chicagoans built large, Gilded Age estates along the lake. These estates can be visited by taking a walk along the Lake Geneva Shore Path, which is one of the top attractions for the town. This 26-mile path provides lakefront views and the opportunity to see the gilded mansions up close. 

If you’re looking for a little adventure, there are a ton of outdoor activities to choose from all year round. Think hiking, biking, skiing, snowboarding, and even ziplining.

👉 Pro Tip: When walking along the Lake Geneva Shore Path, homeowners ask that guests be respectful and refrain from wandering up into their yards. The homes themselves are still private property.

Indiana Dunes National Park, IN

Scenic view from Lake Michigan
There’s nothing like a day spent on Lake Michigan

Distance from Chicago: 1 hour | Google Maps | Indiana Dunes Website 

If you’re looking for an experience similar to Sleeping Bear Dunes, then Indiana Dunes National Park on Lake Michigan’s southern shore is a great option close to Chicago. The park is open all year long and is known for its beautiful beaches and tall sand dunes including Mt. Baldy–the tallest dune in the park. 

Whether you plan on spending a few hours or a full day at Indiana Dunes, there’s no limit to what you can do. Take a hike and swim in the lake during the warmer months, and go cross country skiing when visiting Chicago in the winter. Bird watching is also a popular activity. 

When in doubt, simply sit on the beach and enjoy an incredible sunset. On a clear day, you can actually see the Chicago skyline across the lake!

👉 Pro Tip: Looking for a relaxing walk? The boardwalk and trails at West Beach are a good option. Note that there may be entry fees.

Michigan City, IN

View of a lake along Michigan City
Michigan City is one of many lakefront towns along Lake Michigan’s southern shore

Distance from Chicago: 1.25 hours | Google Maps | Michigan City Website

Although Michigan City (which is in Indiana by the way–I know, a little confusing), is near the Indiana Dunes National Lakeshore, it’s still a good day trip to make on its own. 

Spend some time exploring Michigan City’s Washington Park and Beach area. The park sits on a stretch of the Lake Michigan coastline just outside of town and has tons of activities for the whole family to enjoy. 

On a day when the waves are calm, take a walk on the pier and enjoy a lakeside picnic. If you’re looking for something more interactive, Washington Park Zoo and the Old Lighthouse Museum are good options. Lake activities like boat tours and kayaking are also available in the warmer months.

👉 Did You Know? Washington Park is home to Indiana’s only working lighthouse.

South Bend, IN

View of the University of Notre Dame Golden Dome and a Basilica from the outside
An iconic campus to explore

Distance from Chicago: 1.75 hours | Google Maps | South Bend Website 

At first glance, you might not be familiar with South Bend, Indiana. But, chances are, you’ve heard of its nearby university: Notre Dame. 

The city of South Bend is just under 2 hours from Chicago. For a day trip, start at the South Bend Farmer’s Market for some shopping and a light meal at the cafe (located in the center of the market). If museums are your thing, the Studebaker National Museum and Snite Museum of Art are good options. 

Lastly, a trip to South Bend would be incomplete without a visit to Notre Dame’s beautiful campus. Check out Notre Dame Stadium and end your trip by exploring Basilica of the Sacred Heart–a stunning, Gothic-style church with frescoes and gold detailing.

👉 Pro Tip: Entry to the Basilica is free. If you’re wanting to see the inside of the church outside of mass hours, be sure to visit in the afternoon. 

Oglesby

View of a waterfall from a cave in Oglesby
A zen escape

Distance from Chicago: 2 hours | Google Maps | Oglesby Website 

When you think of Illinois, you probably don’t think of waterfalls. But, along the Illinois River southwest of Chicago, is the town of Oglesby. This is the perfect landing spot for nature lovers to spend the day at Starved Rock State Park and Matthiessen State Park, which are only a 5-minute drive from each other. 

Visit Starved Rock State Park during the springtime to see the canyon waterfalls that come from heavy rain and melted snow. This state park is family-friendly and anyone in decent shape can do these hikes. In total, Starved Rock State Park has 18 canyons and 13 miles of trail and forest to explore. 

For some hiking trails, picnicking, and waterfalls just a little more off the beaten path, head to Matthiessen State Park. This state park has peaceful trails, cool geological features to see, and abundant flora and fauna. 

For some fresh air and outdoor adventure, this is one of the best day trips from Chicago.

👉 Did You Know? Starved Rock State Park is actually one of the best places in the country to see Bald Eagles.

Chicago Botanic Garden

View of a small bridge in Chicago Botanic Garden
The Japanese Garden is one of many themed gardens to see

Distance from Chicago: 30 minutes | Google Maps | Chicago Botanic Garden Website

Another one of the best day trips from Chicago, plan to spend at least a couple of hours wandering this garden gem just north of Evanston. 

The Chicago Botanic Garden is a 385-acre garden filled with countless varieties of flowers and lush greenery. Visitors of all ages can enjoy strolling through the themed and landscaped gardens or natural areas. Along the walkways, visitors will find an ample amount of benches to sit and rest if need be. A tram is also available for those who’d rather ride through the popular gardens or are unable to walk. 

For transportation to Chicago Botanic Garden, driving is the quickest option. However, public transportation from downtown Chicago is available, too. The garden is open every day and all year round for you to enjoy. Just note that hours can vary based on the season. 

👉 Pro Tip: Purchase tickets online and in advance to get the best pricing. The website will also have you choose a specific time slot.  

Oak Park

The Frank Lloyd Wright Home and Studio from the outside in Oak Park
The Frank Lloyd Wright Home and Studio is one of the most iconic places in Oak Park (photo: Thomas Barrat / Shutterstock)

Distance from Chicago: 30 minutes | Google Maps | Visit Oak Park | 👉 Frank Lloyd Wright’s Home Tour

About 9 miles west of Chicago’s downtown Loop is the Oak Park neighborhood. This historic neighborhood is best known for the homes of two iconic American figures: famous architect, Frank Lloyd Wright, and influential writer, Ernest Hemingway. 

For art lovers and architect aficionados, this nearby city neighborhood is one of the best day trips from Chicago. 

To get the most out of a day spent in Oak Park, be sure to visit the Frank Lloyd Wright Home & Studio as well as Ernest Hemingway Birthplace Museum. These two destinations are within two blocks of each other, making it easy to see both. Lastly, downtown Oak Park offers great shopping, restaurants, and places for the arts. 

👉 Pro Tip: If you’re coming from Chicago and want to take the “L,” take the Blue Line headed for Forest Park and get off at the Austin stop. This is an hour-long train ride, but a good way to get some extra sightseeing in while you’re at it. 

Door County, WI

Aerial view of the Cana Island Lighthouse and the blue water around it
Cana Island Lighthouse peaks out on the beautiful Lake Michigan coastline

Distance from Chicago: 3.75 to 4 hours | Google Maps | Door County Website | 👉 Cave Point Kayak Tour

Nature lovers, get ready for one of the most scenic day trips from Chicago. Door County is a county made up of more than 10 small towns situated on the peninsula outside of Green Bay, Wisconsin. The area is famous for its natural beauty, parks, and plethora of outdoor activities. Although a trip to Door County can be made in one day, a long weekend is the best way to experience this gem. 

Lake Michigan is the real star of the show here, and luckily, there are many places and ways to enjoy its beauty. Visit Cave Point for picturesque views of limestone cliffs, as well as hiking, swimming, and kayaking. Door County is also home to 11 beautiful lighthouses and unique activities like shipwreck diving.

🛏️ Need a Hotel? The town of Sturgeon Bay is a great landing spot for other Door County activities. For a homey feel and touch of history, stay at the Scofield House B&B. Looking for a little more privacy? The Westwood Shores Waterfront Resort offers suite accommodations and lakefront views. 

Madison, WI

Aerial view of Madison in Wisconsin
The Wisconsin State Capitol peaks out above Madison

Distance from Chicago: 2.5 hours | Google Maps | Madison Website 

It might be easy to overlook a day trip to Wisconsin’s capital, but Madison is a city worth visiting for its quintessential American look and feel. 

Drive 2.5 hours northwest of Chicago and you’ll be greeted with stunning views of the capitol building’s dome peeking out above the skyline. Not to mention, the city is situated on an isthmus between Lake Mendota and Lake Monona, making for great views and awesome photo ops. Overall, Madison is a place for the whole family to enjoy a change of scenery. 

Other attractions include the Olbrich Botanical Gardens, Henry Vilas Zoo, and fun museums for your kids to explore. 

Monroe, WI

View of cars and establishments from a small town in Monroe
Can’t beat the charm of small town America (photo: Sandra Foyt / Shutterstock)

Distance from Chicago: 2.25 hours | Google Maps | Monroe Website 

When you think of Wisconsin, you probably associate the state with cheese; and a day trip to Monroe will give you just that. Known as “the Swiss cheese capital of the USA,” this central Wisconsin city is famous for its dairy farming. 

To learn more about Monroe and the area’s long-standing cheese history, head to the National Historic Cheesemaking Center. Here, friendly volunteers offer tours and will guide you through the old Imobersteg Farmstead Cheese Factory. 

Once you’ve had your cheese fill, be sure to spend some time in Monroe’s charming downtown. Walk around and enjoy the small-town vibe centered around the historic Green County Courthouse.

Grand Rapids, MI

View of a Japanese Garden in Frederik Meijer Gardens & Sculpture Park
The Japanese Garden at Frederik Meijer Gardens & Sculpture Park

Distance from Chicago: 2.75 hours | Google Maps | Grand Rapids Website

For a smaller city, Grand Rapids is home to an impressive 158-acre garden, park, and outdoor art museum: the Frederik Meijer Gardens & Sculpture Park. For visitors of all ages and interests, this is a must-see part of your day trip from Chicago. Some highlights include The Caterpillar Room, Butterfly Maze, Japanese Garden, and outdoor Sculpture Park.

Grand Rapids is also known as Beer City USA, boasting an impressive craft brewing scene. There’s even a Beer City Ale Trail for visitors to explore 80+ breweries. For foodies, downtown Grand Rapids has farm-to-table cuisine for everyone to enjoy.  

Rockford

View of a pond in Anderson Japanese Gardens during fall season
Head to the Anderson Japanese Gardens for some peace and tranquility

Distance from Chicago: 1.5 to 2 hours | Google Maps | Rockford Website 

Another one of the top day trips from Chicago, Rockford is a big city with a small-town feel located in the rolling hills of northern Illinois. Sometimes called “the city of gardens,” this day trip destination is known for its plethora of gardens, conservatories, and arboretums. Among their most popular is Anderson Japanese Gardens. Here, you can explore 12 acres of beautifully landscaped paths, water features, and Japanese architecture. 

This city is also a great destination for families with young children. There are tons of kid-friendly and interactive museums to choose from like the Burpee Museum of Natural History (featuring amazing dinosaur displays!) and the Discovery Center Museum for hundreds of hands-on exhibits.

If you’re looking to get out into nature while in Rockford, check out Rock Cut State Park. Hiking trails are plentiful and canoeing and kayaking are popular activities. Rockford has something for everyone!

Peoria

View of the skyline in Downtown Peoria and the reflection of it in Illinois River
Downtown Peoria backdropped behind the Illinois River

Distance from Chicago: 3 hours | Google Maps | Peoria Website

A few hours from Chicago is Peoria, a classic river town situated in the center of the state along the Illinois River. In the 19th century, it was nicknamed “the whiskey capital of the world.” Today, Peoria still offers an array of beer, wine, and whiskey options. It also boasts a vibrant arts and culture scene for the whole family to enjoy.  

One of the city’s largest attractions is the Peoria Riverfront Museum. This arts, science, and history museum is an educational must-see. Not to mention, it has a planetarium, too. Another wonderful feature of Peoria’s arts and culture scene is the Peoria Civic Center. Here, everyone of all ages and interests can enjoy a packed calendar of events and performances all year long. 

🏖️ Read Next: 14 Best Beaches in Chicago

Galena

A woman sitting on a chair admiring the view in Grant Park
Fall in love with this charming small town

Distance from Chicago: 3 hours | Google Maps | Galena Website 

In northwestern Illinois, just 3 hours from Chicago, is the town of Galena. With its historic sites and small-town charm, it’s easy to see why this destination often makes the list for things like “best small towns in America.” As far as day trips from Chicago go, Galena is perfect for families, and couples looking for a quaint, romantic getaway. 

The untouched history of this town is what really sets it apart. Places like the Ulysses S. Grant Home, Belvedere Mansion, and Dowling House (which is the oldest building in Galena) are just a few of many historic sites. 

Just outside of town, visitors can spend some time outdoors at Apple River Canyon State Park or Horseshoe Mound Preserve. Blaum Bros Distilling Co. is another popular attraction for those interested in fine spirits and the distilling history of Galena. 

👉 Pro Tip: Miss Kitty’s Grape Escape is a local favorite for drinks, live music, and all-around good vibes.  

🛏️ Need a Hotel? For couples, stay at Farmers Guest House, a bed and breakfast within walking distance of downtown Galena. For families, Stoney Creek Inn Galena is a good option that’s also close to downtown. 

New Glarus, WI

A bowl of cheese fondue on a table
Stop for some cheese fondue!

Distance from Chicago: 2.75 to 3 hours | Google Maps | New Glarus Website 

For visitors of all ages, New Glarus is one of the most unique day trips from Chicago. Originally named after Glarus, Switzerland, this charming Wisconsin town is now known as “America’s little Switzerland.” 

New Glarus will give you a Swiss experience with a midwestern touch. In the town center, you will find Swiss heritage all around. There are chalet-style buildings, specialty shops, and two museums. The town also puts on Swiss festivals and events throughout the year. For that extra touch of Switzerland, visit during the Wilhelm Tell Festival in early September, the New Glarus Oktoberfest in late September, and the New Glarus Christkindli Market in early December. Check the website for the full list of events and dates.

For a taste of Switzerland (and maybe some cheese fondue?) head to the Chalet Landhaus Restaurant or Glarner Stube. The Swiss Historical Village Museum is another great place to immerse yourself in the town’s unique history. For beer aficionados, be sure to check out New Glarus Brewing Co. for a taste of its famous Spotted Cow beer. 

🛏️ Need a Hotel? Book the Fairfield Inn & Suites by Marriott Madison Verona for a comfortable stay with modern amenities. Or check out Nilani’s guide to staying in Chicago for more accommodation suggestions.

FAQ’s About Day Trips from Chicago

What cities are 2 hours from Chicago?

Milwaukee is the largest city within a 2-hour driving distance of Chicago. Other smaller cities within 2 hours of Chicago include Rockford, IL, Michigan City, IN, and South Bend, IN. 

Where should I go from Chicago by car?

Chicago day trips that require a car to go include national and state parks like Indiana Dunes National Park, Starved Rock State Park, and Matthiessen State Park. As far as cities go, Chicago is pretty car-friendly and generally easy to navigate. You can reach almost any destination via car.

Where should I go on a road trip from Chicago in winter?

Lake Geneva, Michigan City, and Door County are good options for winter road trips from Chicago. The roads are almost always salted, making most roads around the city safe for driving in Chicago.

🌇 Read Next: 33 Best Things to Do in Chicago (By a Local)

***

Thanks for reading my list of the top 17 unique day trips from Chicago! As a Chicago local, I’m constantly on the lookout for great day trips, and I hope you have a blast exploring all the area has to offer. 

For more midwestern USA inspiration, check out these 33 unique things to do in Minneapolis

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.