Are you looking for some great Midwest 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. This way, everyone in your group can find something to enjoy!
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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 plan checks all the boxes so you can have a vacation to remember!
This 7-10 day itinerary is best in the summer when you can enjoy the warm weather and fun summertime festivals. Ready for a great road trip? Come join me!
Best Midwest Road Trip Itinerary
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.
There are countless great activities to experience in Chicago! 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.
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. 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. It is home to the most significant collection of Impressionist and Post-Impressionist art outside of the Louvre in Paris.
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!
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!
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.
And, 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. You can also partake in fun activities from the shores of the Chicago River, such as renting a kayak or taking an 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).
See the unique Chicago architecture from the river and save some wear and tear on your feet. Plus, learn all kinds of interesting information from your guide about the buildings and the history of Chicago.
Tip: 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!
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.
Madison is the capital of Wisconsin, so one of the best things to do in Madison is to visit the Capitol building. The 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).
You can tour the Capitol building for free. Admire the multicolored granite and marble inlays decorating the Capitol. 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.
Madison is also a college town, home to the University of Wisconsin-Madison campus. It is worthwhile to stroll through the sprawling campus and enjoy the architecture of the campus buildings.
The university campus is where you will 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.
There are plenty of great ways to enjoy nature in Madison. Check out the Arboretum at the University of Wisconsin. The 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.
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!
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. Then 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 has plenty of gorgeous waterfront parks to enjoy. 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 is a fantastic destination for art lovers. You will find sculptures and public art scattered throughout the city. Visit Black Cat Alley to admire the incredible murals. With a collection of over 30,000 works of art, the Milwaukee Art Museum is the largest in Wisconsin and one of the top attractions in Milwaukee. You will want to see its unique architecture, with stunning Burke Brise Soleil wings that can open and close.
Milwaukee is home to some 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.
Milwaukee is also the location of SummerFest, one of the largest music festivals. 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.
You will notice the German heritage of the city when you visit Old World 3rd Street. Milwaukee hosts one the largest GermanFests in the United States and is also 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.
Milwaukee was made famous by its many breweries. That is how it earned the nickname the beer capital of the world. You can learn more by taking a beer history tour or brewery tour during your visit to Milwaukee.
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.
Whether your idea of a perfect vacation day is visiting a museum or relaxing in a park, you will have a great time on this classic road trip through the Midwest!
Author bio: Lisa Garrett
Although she works full-time in the semiconductor industry, Lisa travels as much as possible throughout the year. Her travel blog, Waves and Cobblestones, is chock-full of city guides and destination tips to help you make the most of your vacation time.
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