Best Chicago Road Trip to Wisconsin: Midwest Fun!

Are you looking for great Chicago road trip ideas?  

Planning amazing road trips can be a challenge. The first step is to pick a good mix of cities that have a diverse array of activities.

At least one city needs a good airport so that it is easy to reach. The additional destinations should be close to each other geographically to avoid wasting too much time on the road.

I have the perfect Midwest road trip itinerary for you right here! This 7–10-day road trip is best in the summer when you can enjoy the warm weather and fun summertime festivals.

Ready for a great road trip from Chicago? Come join me!

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Chicago, Illinois

Chicago is the best city to use as the starting location for your road trip. It is easy to get to the Windy City from just about any destination — domestic or worldwide — via the O’Hare International Airport.

Field Museum

The Field Museum is another perennial favorite for visitors to the Windy City (and is part of the Chicago Museum Campus).

This natural history museum has diverse collections ranging from Ancient Egypt to meteorites. It also has extensive taxidermy exhibits containing hundreds of species of birds.

But the star of the Field Museum is Sue. Sue is the skeleton of a Tyrannosaurus Rex — the largest one ever discovered!

(Traveling with the family? The Field Museum is one of the best museums in Chicago for kids!)

Art Institute of Chicago

Chicago is home to an incredible number of world-class museums. If you enjoy museums, you are going to love visiting Chicago!

Art lovers will want to plan a visit to the Art Institute of Chicago, or “AIC”.

This venerable museum was founded in 1879 and is one of the largest art museums in the world, with over 300,000 works of art (wow!).

It is home to the most significant collection of Impressionist and Post-Impressionist art outside of the Louvre, one of my favorite attractions in Paris. (I love Impressionist art!)

Grant Park / Buckingham Fountain

When visiting Chicago, one of the best things to do is to take a walk. Relax as you enjoy the parks and green spaces scattered throughout the city. 

Grant Park is one of the most popular parks in Chicago. This is where you can see Buckingham Fountain, a stunning 3-story rococo fountain. Be sure to get a photo of this beautiful fountain with the iconic Chicago skyline as the background!

Millenium Park / Cloud Gate

Another must-see destination in Chicago is Millenium Park.

This is where you will find the unique Cloud Gate sculpture, affectionately called the Bean. Like a fun-house mirror, the mirrored surface of this one-of-a-kind sculpture reflects its surroundings.

This park is also home to the Jay Pritzker Pavilion, a bandshell designed by famous architect Frank Gehry. Many musical events are held in this open-air pavilion, including a free summer music series.

Chicago RiverWalk

No trip to Chicago is complete without a walk along the Chicago RiverWalk!

This space is chock-full of restaurants and bars where you can enjoy famous Chicago foods, such as deep-dish pizza and Chicago-style hot dogs.

Looking for some fun activities on the shores of the Chicago River? Try renting a kayak or taking an architectural river cruise!

Architectural River Cruise

One great way to get introduced to Chicago is to take an architectural river cruise. 

The Chicago skyline consists of a dazzling array of skyscrapers, from the Willis Tower (with the highest observation deck in the United States) to the Marina Towers (called Corn Cob Towers by locals).  

A river cruise is the best way to see Chicago’s incredible architecture.

Plus, you’ll learn all kinds of interesting information from your guide about the buildings and the history of Chicago. (Our guide was an architecture major, and her enthusiasm was contagious!)

Chicago Travel Tips

Tip #1: Chicago has an excellent public transit system. If you plan to spend most of your time downtown, get around on foot and use public transportation.

This will help you to save money on your car rental (and avoid sky-high city parking fees). Then pick up your car on your way out of town!

Tip #2: Do some reading before your trip to see which attractions are best for you. If you want to do it all, you may be able to save some money by purchasing city passes that cover many of the top attractions in Chicago.

Madison, Wisconsin

Your next stop on this Midwestern road trip is Madison, Wisconsin. Madison is only about a 2.5-hour drive from Chicago, so you will have plenty of time to explore the city once you get there.

Wisconsin Capitol Building

Madison is the capital of Wisconsin, so one of the best things to do in Madison is to visit the Capitol building.

The Wisconsin Capitol building is a stately and impressive structure, complete with classic columns and topped with an immense dome (the largest granite dome in the world).

Best of all, you can tour the Capitol building for free!

Be sure to climb to the observation deck of the dome and stroll around the perimeter. From here, enjoy gorgeous panoramic views of Madison and the surrounding lakes, Lake Monona and Lake Mendota.

Chazen Museum of Art

Madison is also a college town, home to the University of Wisconsin-Madison campus. (And my dad’s alma mater!)

Take a stroll through the sprawling campus and enjoy the architecture of the campus buildings.  

This is also where you’ll find the Chazen Museum of Art. The lovely museum is free and contains a fabulous and diverse collection of art, ranging from the Italian Renaissance to sculpture and Oriental arts. 

There are even works of art from world-famous artists such as Pablo Picasso, Joan Miró, and Andy Warhol.

Arboretum

There are plenty of great ways to enjoy nature in Madison, including exploring the Arboretum at the University of Wisconsin.

The massive Arboretum spans 1200 acres and contains specimens from habitats ranging from conifer forests to prairies. If you enjoy hiking, this is the best place in Madison for you!

Olbrich Botanical Gardens

Another must-see attraction in Madison is the Olbrich Botanical Gardens. The outdoor gardens are free (although there is a small fee if you want to check out the displays in the Bolz Conservatory).

You must see the Thai pavilion and garden, one of the highlights of the Botanical Gardens.

The Thai pavilion is one of only four outside of Thailand. The stunning pavilion is completely covered in gold leaf. So look, but do not touch!

(Love gardens? Check out this post about the Montreal Botanical Gardens!)

Mount Horeb

For a unique day trip from Madison, visit Mount Horeb, one of the quirkiest small towns in Wisconsin.

Mount Horeb is about 30 minutes west of Madison and bills itself as The Troll Capital of the World. Stop by Main Street to check out all of the carved troll statues.

Venture further down the road to see the natural wonders of Cave of the Mounds State Park. Go spelunking and see the unique rock formations in these limestone caves.

Milwaukee, Wisconsin

The last stop on your road trip through the Heartland of America is the fabulous city of Milwaukee, Wisconsin. From Madison, drive an hour and a quarter east to reach Milwaukee.

Milwaukee is located on the banks of Lake Michigan, where several rivers flow into the lake.

Milwaukee River Walk

You’ll want to spend time in Milwaukee’s gorgeous waterfront parks. Enjoy a stroll or paddle a kayak along the Milwaukee River Walk.

Check out the public art along the river, including the life-sized statue of the Bronz Fonz. (This is a nod to the TV show, Happy Days, set in Milwaukee).  

Milwaukee Art Museum

Milwaukee is a fantastic destination for art lovers!

With a collection of over 30,000 works of art, the Milwaukee Art Museum is the largest in Wisconsin and one of the top Milwaukee attractions. You will want to see its unique architecture, with stunning Burke Brise Soleil wings that can open and close.

(Prefer street art to museums? Then don’t miss the amazing murals in Black Cat Alley!)

Unique Milwaukee Museums

Milwaukee is home to some cool one-of-a-kind museums. Motorcycle enthusiasts will want to visit the only Harley-Davidson Museum in the world. 

And for an offbeat experience, visit the National Bobblehead Hall of Fame and Museum. It is the only bobblehead-focused museum, with a collection of 10,000 bobbleheads from around the globe.

Old World 3rd Street

You will notice the German heritage of the city when you visit Old World 3rd Street.

(Did you know that Milwaukee hosts one the largest GermanFests in the United States and is a great place to celebrate Oktoberfest?)

Bratwurst and sausages are a staple on Milwaukee menus, alongside fried cheese curds (you are in Wisconsin, after all) and local brews.  

Why not learn about Milwaukee’s beer history (and sample some local favorites) on a brewery tour during your visit?

SummerFest Music Festival

Milwaukee is also the location of SummerFest, one of the largest music festivals in the world!

This celebration of music is held for three weekends at the end of June and early July.

Hundreds of bands perform at SummerFest, so there is certainly something for any music lover to enjoy.

Getting Back Home

You can choose to end your road trip in Milwaukee and fly out of the General Mitchell International Airport.

A second option is to close the loop and return to Chicago, where you started.

The route from Milwaukee to Chicago is only a 1.5-hour drive, so it is a good choice if you prefer having more flight options from the larger Chicago airports.