10 Amazing Midwest Road Trips [2024]

Breathtaking autumn vista from a high vantage point on a Midwest road trip, overlooking a patchwork of fall foliage, tranquil water bodies, and distant towns.

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 landscape, 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 encourage others to do the same! 

Imagine starting your journey in the bustling streets of Chicago, then meandering through the serene beauty of Indiana Dunes, before being awestruck by the natural wonder of Pictured Rocks.

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

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 the ferris wheel at Navy Pier. 

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

Illinois State Parks: Starved Rock and Matthiessen

Stepping stones lead to a wooden staircase beside a small waterfall at Matthiessen State Park. The lush greenery and serene water create a perfect hiking backdrop.
Matthiessen State Park

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

St. Louis Arch by Chris Hardy via Unsplash

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! 

A road trip combining the natural beauty of Shawnee National Forest in Southern Illinois with the urban sprawl of St. Louis offers an unparalleled mix of city exploring, a national park, and outdoor adventures.

Starting in St. Louis, visitors can marvel at the Gateway Arch, explore the city’s vibrant food scene, and stroll through the historic neighborhoods before heading towards Shawnee National Forest.

The drive itself, which takes you directly into the heart of Southern Illinois, is scenic and tranquil, setting the stage for the adventure ahead.

Shawnee National Forest, with its expansive landscapes, hiking trails, and unique formations such as the Garden of the Gods and Cave-In-Rock, provides a stark contrast to the city’s hustle and bustle.  It easily features some of the best Midwest hiking trails. 

This road trip encapsulates the essence of the Midwest – a blend of urban exploration and the tranquility of nature.

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

An urban outdoor seating area in Milwaukee, featuring modern architecture with steel beams and glass canopies, set against a brick building with a faded mural. The inviting space, ideal for a leisurely spring break afternoon, blends contemporary design with historic elements.
Milwaukee by Tom Barrett via Unsplash

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 compelling destination for any traveler seeking a taste of Midwest charm.

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 city, 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 will relish exploring the extensive network of bike trails and the serene beauty of the UW Arboretum.

Route: Setting out from Milwaukee, you will take I-94 West, 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

3 – 4 Day Road Trips

Route 66: Chicago to St. Louis

Breathtaking view of Chicago's skyline from the Willis Tower, showcasing the city's architectural beauty, a must-see on a girls weekend in Chicago.
Chicago Skyline

Best for: Cities and hidden gems

Ah, Historic Route 66!   The quintessential American road trip that 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 and visit the famous Budweiser Clydesdales at the Anheuser-Busch Brewery. 

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

Pure Michigan: Small Towns and Beaches

New Buffalo, Michigan

Best for: Beaches

Pure Michigan didn’t gain it’s 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. 

If you’re keen, visiting Michigan wineries is also a staple of the region. 

Tip: This also makes for an amazing Midwest spring break

Badlands National Park: South Dakota

The Badlands' rugged landscape at dusk, with layered rock formations and eroded buttes standing prominently against the hazy sky. The dramatic scenery is a testament to the natural wonders found in the Midwest, perfect for a spring break road trip adventure.
Badlands National Park by Michael via Unsplash

Best for: Adventure

A road trip through Badlands National Park in South Dakota is an adventure that encapsulates the raw beauty and immense landscape of the American West.

The park’s rugged terrain, marked by layered rock formations, steep canyons, and towering spires, calls to those seeking solitude and exploration.

Key stops should include the Ben Reifel Visitor Center to gather insights into the area’s geology and history, the striking Panorama Point for unforgettable panoramic views, and the Roberts Prairie Dog Town to watch these amusing animals in their natural habitat.

For those seeking to immerse themselves deeper into the wilderness, the park offers hiking trails that range from the easy Window and Door trails to the more challenging Saddle Pass.

Over three to four days, visitors can enjoy hiking, stargazing under one of the darkest night skies in the country, and wildlife watching, with the chance to spot bison, bighorn sheep, and prairie dogs, making a road trip through Badlands National Park truly worth it.

Route: Begin your adventure by driving the Badlands Loop Road (Highway 240), which offers stunning views and numerous overlooks to capture the unique topography.

Miles: 31

5-7 Day Road Trips

Upper Peninsula: Michigan

Cliffside view of a serene cove with crystal-clear turquoise waters along the coast of Lake Superior, framed by lush greenery. Kayakers enjoy the calm waters near a notable rock formation, making it an idyllic Midwest spring break destination for nature lovers and outdoor enthusiasts.
Pictured Rocks by Laura Heuer via Unsplash

Best for: Kayaking and hiking

Visiting the Upper Peninsula in Michigan is truly an adventure worth taking, especially for those passionate about kayaking, hiking, and immersing themselves in pristine natural surroundings.

The highlight of this region is undoubtedly the Pictured Rocks National Lakeshore, where the stunningly colorful cliffs soar above Lake Superior, creating a breathtaking panorama that is unmatched anywhere else.

Over a span of 5-7 days, travelers can deeply explore the diverse landscapes that range from dense forests to sparkling waterfalls, with scenic stops at Marquette for its rich history and vibrant arts scene, and the Keweenaw Peninsula for a glimpse into the area’s mining past.

This duration allows for an unhurried exploration of the key attractions, various hiking trails, and ample time for kayaking along the coastline, enveloped by the sheer beauty of the cliffs.

Route: The road trip route, starting from St. Ignace, moving westward along the coast to Pictured Rocks, then circling up through Houghton to Copper Harbor and back, offers an unforgettable experience.

Miles: 42

Mackinac Island

Mackinac Island by Vincent Yuan via Unsplash

Best for: Relaxation and adventure

Mackinac Island, set amidst the sparkling waters of Lake Huron, stands as an essential detour in any Michigan road trip for those seeking both relaxation and adventure.

Top stops on the island include the historic Fort Mackinac, the enchanting Arch Rock, and the bustling downtown with its fudge shops and boutique stores.

For a comprehensive Michigan adventure, road trippers often combine a visit to Mackinac Island with the scenic drives to the Upper Peninsula or exploring the Sleeping Bear Dunes National Lakeshore, both of which offer unparalleled natural beauty and outdoor activities.

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.

The Great River Road: Wisconsin and Minnesota

La Crosse, Wisconsin by Fern M. Lomibao via Unsplash

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.

Whether you’re an outdoor enthusiast or just looking for a peaceful and scenic drive, the Great River Road has something for everyone. 

Additionally, this route is also a great opportunity to learn about the history and culture of the region, with many museums and historical sites scattered along the way.

Don’t forget to try some local delicacies like Wisconsin cheese curds and Minnesota’s famous wild rice dishes while you’re on your adventure!

Overall, the Great River Road offers a unique and diverse experience for travelers, making it a must-see destination for your next road trip.

Route: Travelers will primarily follow State Highway 35 in Wisconsin and State Highway 61 in Minnesota, providing seamless access to the river’s wonders and beyond.

Miles: 360

Midwest Road Trip FAQ

Q: What’s the best time of year to undertake 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, offering optimal conditions for outdoor activities and exploration.

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 as well.

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 months, to secure the best locations.

Q: Is it easy to find accommodation, or should I book in advance?

A: While there are many accommodation options available, including hotels, motels, and Airbnb rentals, 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.

  • 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

Exploring the Midwest through road trips presents first-time visitors with an unparalleled opportunity to 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”!

Remember to prepare well, stay flexible, and open yourself up to the experiences and stories waiting for you along these scenic routes. Safe travels!

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As a full time employee who loves her job, learn how I honor my wanderlust while working a 9:00-5:00 (because I want to!) This blog welcomes all, and specifically provides resources for those seeking travel intertwined into a busy schedule (3 days to 5 weeks).