Considering a Midwest road trip? One of the most underrated and under-explored areas of the United States provides a refreshing perspective on hidden beauty!
Explore bustling cities, hidden landscapes, and great vibes.
Many top destinations in the Midwest are spread out. I recommend pairing your Midwest road trip activities by location to experience the best activities with less time in the car!
As a Midwest local, I have experienced many of these road trips firsthand and love any opportunity to get off the beaten path in my home region, and I encourage others to do the same!
These destinations exemplify the diverse experiences the Midwest has to offer, from urban exploration to the tranquility of nature and the nostalgia of historic paths less traveled.
Let’s uncover the best Midwest road trips for unique and memorable adventures!
1 – 2 Day Road Trips
Chicago to Indiana Dunes
Best for: City and nature
Chicago to Indiana Dunes is one of my favorite road trips from Chicago! This easy road trip is just over an hour and welcomes you to a whole new world outside of the windy city.
Chicago is one of the best cities in the United States for so many reasons. Experience top attractions like “The Bean” (or Cloudgate) or Navy Pier’s infamous Ferris Wheel.
Some of my favorite off-the-beaten-path activities include exploring Wicker Park and the city’s free conservatories. I can’t get enough of a Chicago trip.
After a full day of city exploring, drive one hour by car (OR catch a train at Chicago Union Station) to Indiana Dunes National Park.
Some of the best Indiana Dunes hiking trails include the 3 Dune Challenge and Dune Succession Trail. Sandy adventures overlooking Lake Michigan await on this road trip that combines urban and natural adventure!
Route: Starting from the heart of Chicago, the route to Indiana Dunes National Park primarily follows the I-90 East highway.
Exiting the bustling cityscape, the drive transitions into the scenic landscapes of Northern Indiana. The drive is straightforward and smooth.
Miles: 38
⭐Stay: Drake Hotel
Illinois State Parks: Starved Rock and Matthiessen
Best for: Nature
My next favorite place to experience serenity outside of the bustling city is at Starved Rock and Matthiessen State Parks.
You can easily explore both state parks on a quick-paced day trip from Chicago or Milwaukee.
Matthiessen and Starved Rock are located only 10 minutes away from one another- two state parks for the price of one? Priceless!
Actually… free! That’s right, this extremely inexpensive road trip allows you to cross off some of the best Midwest hiking for zero dollars.
Some of the best things to do in Starved Rock and Matthiessen are hiking, chasing waterfalls, and exploring sandstone canyons.
Route: Starting from Chicago, take I-55 S toward St. Louis, then merge onto I-80 W towards Iowa. Exit for IL-178 N and proceed towards Utica.
Miles: 93
Southern Illinois and St. Louis
Best for: City + Adventure Combo
Southern Illinois is often overlooked as a vacation destination, but it is unlike any other because it features Shawnee National Forest!
Begin your road trip in St. Louis with a ride to the top of the Gateway Arch for views of the Mississippi River.
Spend time at Forest Park, home to the Saint Louis Art Museum and the Science Center.
Walk through the Delmar Loop or grab barbecue in The Hill, a historic Italian neighborhood.
Then, drive two hours southeast to Shawnee National Forest in Illinois.
It easily features some of the best Midwest hiking trails!
Explore Garden of the Gods, with its dramatic sandstone cliffs, hike through Giant City’s maze-like rock paths, and relax by the lakes in the Shawnee Hills.
The contrast between city landmarks and rugged forest makes this road trip diverse and rewarding.
Route: From St. Louis, drive east on I-64, taking in the urban landscape as you exit the city.
Miles: 134
Wisconsin Cities: Milwaukee and Madison
Best for: Urban Vacation
Milwaukee is often referred to as Chicago’s younger sibling.
Less than a two-hour drive away from the windy city is neighboring Milwaukee, filled with its own style and flair.
Milwaukee’s vibrant blend of cultural attractions, historical landmarks, and culinary delights makes it a destination worth visiting!
My personal favorite in the Milwaukee Public Market! I say it time and time again.. I LOVE a good market. (From Seattle to Lisbon, it’s just kind of my thing).
Just over an hour north is Madison, an even bigger metropolis, perhaps most famous for its Badgers Football (which you can plan to see EVERYwhere).
A visit to the State Capitol building provides an awe-inspiring view of the city and an educational glimpse into the state’s history.
Meanwhile, outdoor enthusiasts can explore Wisconsin’s extensive network of bike trails and the beauty of the UW Arboretum.
Route: Setting out from Milwaukee, you will take I-94 West. This is a direct route that cuts through the heart of Wisconsin’s picturesque landscapes.
The drive covers approximately 80 miles and takes just under 1.5 hours.
Miles: 80
⭐Highly Rated Milwaukee Tours
3 – 4 Day Road Trips
Route 66: Chicago to St. Louis
Best for: Cities and hidden gems
Ah, Historic Route 66! The quintessential American road trip stretches from Chicago to Los Angeles.
Although you could easily spend weeks exploring all the sights along the route, we’ll focus on a 3-4 day stretch from Chicago to St. Louis.
Starting in Chicago, make sure to stop by Willis Tower (formerly known as Sears Tower) for stunning views of the city’s iconic skyline.
Don’t forget to take a picture at the official starting point of Route 66 in Grant Park before hitting the road.
The first major stop on this leg of the trip is Springfield, the capital of Illinois and also home to Abraham Lincoln’s Presidential Library and Museum.
From there, continue on through Bloomington and down to St. Louis, where you can see the iconic Gateway Arch.
End your trip with a visit to the charming neighborhood of Soulard, known for its historic buildings and vibrant nightlife.
Tip: For those looking to extend this road trip, continue on to explore more of Missouri or head west towards Kansas City.
Route: Historic 66, the whole way down. That’s it!
Miles: 300
⭐Stay: Hotel Saint Clair
Pure Michigan: Small Towns and Beaches
Best for: Beaches
Pure Michigan didn’t gain its name overnight.
Thanks to the massive Lake Michigan, tons of visitors enjoy this great lake’s glory every year.
Whether it’s experiencing Chicago’s beaches beneath its expansive skyline or relaxing on a long stretch of lakeshore on one of Michigan’s many tiny, gem-filled towns, there is certainly relaxation to be found on Lake Michigan.
Start your road trip off by experiencing Michigan’s coastal beauty in New Buffalo, Michigan. This is one of the best small towns.
Next, stop in Saugatuck and Douglas. Each small town is filled with its own character and charm.
Visiting Michigan wineries is also a staple of the region.
Tip: This also makes for an amazing Midwest spring break!
⭐Stay: Starlite Resort
Badlands National Park: South Dakota
Best for: Adventure
Badlands National Park in South Dakota features jagged rock spires, fossil beds, and vast prairie.
The Badlands Loop Road offers stops like Big Badlands Overlook, Burns Basin, and Pinnacles Overlook for sweeping views. Notch Trail leads through a canyon and up a log ladder to a dramatic cliff edge.
Fossil Exhibit Trail showcases ancient fossils and the area’s geologic history.
Wildlife such as bison, pronghorn, and bighorn sheep are often seen along the road and trails.
Route: Begin your adventure by driving the Badlands Loop Road (Highway 240).
The drive offers stunning views and numerous overlooks.
Miles: 31
⭐Stay: Cambria Hotel Rapid City
5-7 Day Road Trips
Upper Peninsula: Michigan
Best for: Kayaking and hiking
A road trip through Michigan’s Upper Peninsula should include at least 5 days to explore its remote beauty.
Start in Munising to hike or kayak along Pictured Rocks, where multicolored cliffs rise over Lake Superior. Visit Miners Castle, Chapel Rock, and take the boat tour for the best views.
Drive west to Marquette for beaches, breweries, and a hike up Sugarloaf Mountain.
Don’t miss Tahquamenon Falls, the ghost town of Fayette, or sunset at Lake of the Clouds in Porcupine Mountains Wilderness.
Route: The road trip route begins in St. Ignace. It then turns west along the coast to Pictured Rocks. Finally, it circles up through Houghton to Copper Harbor and back.
Miles: 42
⭐Stay: Beach Inn Motel
Mackinac Island
Best for: Relaxation and adventure
Mackinac Island is located on the sparkling waters of Lake Huron.
It’s an essential detour on any Michigan road trip!
Visit historic Fort Mackinac, stroll through downtown shops, and try the island’s famous fudge.
Hike or bike to Arch Rock and enjoy views of Lake Huron from the shoreline.
The island’s slower pace and 19th-century charm make it a one-of-a-kind Midwest road trip stop.
Route: Travelers typically start their journey from the mainland at Mackinaw City or St. Ignace, where they can catch a quick ferry.
Tip: While a National Parks Pass isn’t required here, it’s useful for those combining their trip with visits to nearby national parks.
⭐Stay: Pine Cottage Bed & Breakfast
The Great River Road: Wisconsin and Minnesota
Best for: Scenic drives and outdoor adventures
If you’re looking for a road trip that combines breathtaking scenery and outdoor activities, the Great River Road is the perfect choice.
Starting in La Crosse, Wisconsin, this scenic route follows the Mississippi River all the way to Grand Rapids, Minnesota.
Along the way, you can stop at numerous state parks and wildlife refuges to go hiking, fishing or even spot bald eagles.
Make sure to visit the charming river towns of Red Wing, Minnesota and Pepin, Wisconsin for a taste of local culture and cuisine.
End your trip with a visit to the Headwaters of the Mississippi in Itasca State Park, where you can walk across the iconic source of this famous river.
Don’t forget to try some local delicacies like Wisconsin cheese curds and Minnesota’s famous wild rice dishes!
Route: Travelers will primarily follow State Highway 35 in Wisconsin and State Highway 61 in Minnesota.
Miles: 360
Midwest Road Trip FAQ
Q: What’s the best season for a Midwest road trip?
A: The ideal time for a Midwest road trip is between late spring and early fall, specifically from May to October.
During these months, the weather is warm, and the scenic landscapes are at their most vibrant.
Q: Are there any specific items I should pack for a Midwest road trip?
A: Given the variety of activities and weather conditions you might encounter, it’s wise to pack layers of clothing, comfortable hiking shoes, a rain jacket, sunscreen, and insect repellent.
Don’t forget your camera and a power bank for your devices.
Q: Can I find good camping spots along the route?
A: Yes, the Midwest is home to numerous state and national parks with excellent camping facilities.
It’s recommended to book your camping spots in advance, especially during the peak summer month.
Q: Is it easy to find accommodation, or should I book in advance?
A: Booking in advance is advisable, especially during peak tourist seasons or if you’re visiting popular destinations like Mackinac Island.
Q: How do I prepare my vehicle for the trip?
A: Ensure your vehicle undergoes a thorough check-up before you set out, focusing on its fluids, tires, brakes, and battery.
Also, pack an emergency kit, spare tire, and keep a map or GPS device handy for navigation.
Midwest Road Trip Tips
- All of these itineraries can be reversed- choose whichever order makes most sense for you, or that you like the most!
- Depending on your pace and how long you want to spend in each location, you can easily add or take away stops from these routes.
- Always check weather conditions before setting off on your road trip and plan accordingly.
That’s a Wrap
Taking a Midwest road trip is an amazing way to experience the region!
Travelers can immerse themselves in the region’s vast natural landscapes, cultural sites, and friendly communities.
Whether you’re marveling at the Great Lakes, tackling adventurous trails, or enjoying the local culinary delights, there is something for everyone in this region that isn’t always “mid”!
