A 4-day road trip across three states, Illinois, Wisconsin, and Minnesota, that starts in Chicago and ends in Minneapolis is the best way to explore some natural and cultural gems of the Midwest.
Last updated: January 7, 2026
Chicago to Minneapolis Road Trip: A 4-Day Journey across the Midwest
Summer is the best and the worst time (think the heat and seasonal sites) to travel across the U.S. Longer days and open roads as many Americans vacation abroad play in favor of lengthy road trips. For reference, the entire route from Chicago to Minneapolis with stops in Rockford, Wisconsin Dells, and several gorgeous hidden gems in the Midwest spans approximately 425 miles. In terms of hours, it’s between 6 and 7 hours of driving.
Divide this number by four, and you’ll get roughly 2-3 hours on the road a day. If you’ve ever gone on a road trip, you know how doable and enjoyable this journey from Chicago to Minneapolis can be.
Planning 4-Day Chicago to Minneapolis Road Trip
Our 4-day Chicago to Minneapolis road trip raised some eyebrows. I came to believe that people don’t travel across three midwestern states often, moreover pick up a rental car in Illinois and drop it off hundreds of miles away in Minnesota.
Disbelief mixed with curiosity and a pinch of inspiration – or maybe I was just imagining the latter – were written on the faces of car rental employees and hotel owners when we were filling out some paperwork necessary to use their services.
A road trip across three states in the Midwest is indeed a long endeavor. We broke our journey from Chicago to Minneapolis into four feasible segments, leaving plenty of time a day to get out of the car and explore. From hiking to riding a boat, visiting some hidden lakes and gushing waterfalls, and touring small midwestern towns, this road trip couldn’t be more adventurous.
CHICAGO TO MINNEAPOLIS ROAD TRIP: 4-DAY MIDWEST ADVENTURE
DAY 1: CHICAGO, ILLINOIS
Chicago is one of the biggest cities in the U.S. and home to such iconic sites as Millennium Park with its mirror-surfaced Bean and the glass-bottomed ledges at the Willis Tower Skydeck.
To be precise, Chicago is ranked the third-populous city in the country after New York City and Los Angeles. Thus, with such a diversity and size, you need at least 3 full days to explore everything it offers, dive deeper into its bustling culture, immerse yourself in its culinary scene, and laze at the shore of great Michigan Lake.
We ached to see Chicago, the mighty Michigan Lake, and a few other urban sites, but didn’t have any intention to spend more than one day in the buzzing city during this Chicago – Minneapolis road trip. With technically two places at the top of our itinerary – the Willis Tower with its nerve-racking Ledge and one of the five Great Lakes – we had enough time and were ready to hit the road the next morning.
Where to Stay: We stayed at Best Western Grant Park Hotel. The 3-star hotel offers basic amenities and is located within a walking distance of Grant Park and the Museum Campus. The main downside of the place is the absence of a self-parking lot. The hotel offers only valet parking. You can find a more affordable public parking garage right around the corner.
Alternative Chicago – Minneapolis Itinerary
If you can add at least one more day to your Chicago – Minneapolis road trip, spend the next day in Indiana Dunes National Park. The place is located roughly 40 miles southeast of Chicago along the shore of Michigan Lake and is known for its diverse landscapes and year-round outdoor activities.
DAY 2: CHICAGO, IL – ROCKFORD, IL
Total drive time for the day: 2 hours 30 minutes (175 miles)
Stop 1: Starved Rock State Park, Illinois
If you skip Indiana Dunes National Park during this road trip, leave Chicago early in the morning (the city traffic is not that bad at this time) and head southwest to Starved Rock State Park.
This area enhances your Chicago – Minneapolis road trip with breathtaking canyons, such as French Canyon (arguably the most beautiful), Ottawa Canyon, and La Salle Canyon.
We saw only trickles. But if you drive from Chicago to Minneapolis with a stop in Starved Rock State Park in spring, get ready for a beautiful waterfall excursion. More than a dozen of seasonal waterfalls live within the intricate canyon system of the park.
Stop 2: Matthiessen State Park, Illinois
Just short 5 miles away, Matthiessen State Park expands the midwestern domain with more hidden canyons, a scenic lake that not many wander to, and stunning waterfall-gems. The park was named after the property’s former owner Frederick William Matthiessen.
The waterfalls in this secluded section of the Midwest, which is a short side trip from the straight route that connects Chicago and Minneapolis, also turn on and off their flows in response to the seasonal changes.
In the summer, you can hardly see a trickle where at the right time a roaring waterfall plunges over the cliff. But the coolness of the canyons along with the quiet of the lake are here to enjoy all year round.
Stop 3: Buffalo Rock State Park, Illinois
Buffalo Rock State Park is the last member of the trio. The place is a sanctuary where American bison, once abundant in the area, are preserved and reintroduced into the Midwest. During our visit, only two creatures existed in the state park. The bison dwell in a large, fenced grazing area with a parking lot and plenty of picnic spots nearby.
Buffalo Rock State Park can be a several-minute or a half-day stop on your Chicago to Minneapolis road trip. If you need more time to stretch your legs, hit one of a few hiking trails. Otherwise jump back in the car and head north to the final destination of the day.
Stop 4: Rockford, Illinois
Rockford, a Midwestern town we finished this stretch of our Chicago – Minneapolis road trip in, had a cosy feel about it. Charming and clean (probably one of the cleanest cities we’ve been to in the U.S.) with beautiful architecture, at first it puzzled us with an almost complete absence of pedestrians. It looked like a modern ghost town.
It took us a quick, after-dinner trip to the Rock River to see some friendly locals fishing and strolling along the banks.
Where to Stay: For a mid-size city, Rockford has a big number of hotels, motels, and Airbnbs to choose from. We opted for a simple Airbnb near the downtown area.
DAY 3: ROCKFORD, IL – WISCONSIN DELLS, WI
Total drive time for the day: 2 hours 30 minutes (133 miles)
Stop 1: Devil’s Lake State Park, Wisconsin
About 2 hours north of Rockford lies a lovely lake surrounded by 500-foot quartzite bluffs. It’s a place of unique beauty and one of the most cherished jewels of Wisconsin.
Devil’s Lake State Park is a favorite spot for boating, kayaking, hiking, and rock climbing. The place attracts with its clear natural lake and quaint rock formations, such as Devil’s Doorway, whose colors range from purple to maroon, pink, and white.
TIP: Plan your trip to Devil’s Lake State Park thoroughly. It’s easy to get sidetracked and spend more time here than your 4-day Chicago to Minneapolis road trip allows. A few hours will be enough to hike some rocky trails or kayak on the lake.
Alternative Itinerary: Alternatively, allot more days for your Midwest road trip or skip Wisconsin Dells’ sightseeing and spend the entire day in the Devil’s Lake State Park.
Stop 2: Witches Gulch, Wisconsin
The reason we included Wisconsin Dells in our Chicago – Minneapolis road trip was the gorgeous Witches Gulch. The eerie slot canyon is not even a mile long. But it astounds with its dreamy, almost mystical ambiance and moss-covered guarding bluffs.
The secluded canyon is a seasonal attraction and accessible only by boat tours. There are several tour options you can choose from. We booked a 2-hour Upper Witches Gulch tour with two landings at Witches Gulch and Stand Rock.
Stop 3: Wisconsin Dells, Wisconsin
The central focus of our Chicago – Minneapolis road trip wasn’t the number of places to visit, but the quality and in-depth (as far as the time allowed) experiences. Thus, we didn’t drive far after our Witches Gulch tour came to an end. In fact, we didn’t even move the car from the parking lot behind the boat dock until hours later. Instead, we explored downtown Wisconsin Dells with its many restaurants, shops, and green spaces on foot.
After a quick or hours-long city immersion, you can start looking for solitude in Mirror Lake State Park or Wisconsin Deer Park. The latter is probably not the best choice for the most pristine experience, though.
Where to Stay: A double room at Lakeside Motel was our home for the night. We wished we had one more day to spend at the property. While the rooms were simple (for some people might have been too simple), the motel had access to a lake where it offered free boats and kayaks for guests.
DAY 4: WISCONSIN DELLS, WI – MINNEAPOLIS, MN
Total drive time for the day: 3 hours 30 minutes (225 miles)
Stop 1: Willow Falls, Wisconsin
3 hours 30 minutes was the longest we drove in one day during this Chicago – Minneapolis road trip. We could save some 15-20 minutes had we headed straight to Minnesota after leaving Wisconsin Dells. But the opportunity to see one of the most beautiful waterfalls in the Midwest was too irresistible.
Willow Falls is the central landmark in Willow River State Park. At 45 feet high and about 100 feet wide, it’s not the tallest or largest waterfall in the region. But cascading over three prominent ledges, it’s a sight to behold.
A wide, well-trodden and partially paved trail leads to Willow Falls and an observation deck overlooking the park. Several trails dive deeper into the forest. You can hike along and admire the beauty of the region in more detail.
Our time, however, was limited. Although we didn’t rush, we were aware of the clock ticking. Our 4-day Chicago to Minneapolis road trip was coming to an end and we still had two more cities to explore.
Stop 2: St. Paul – Minneapolis, Minnesota
Separated by the Mississippi River, St. Paul and Minneapolis are known as the Twin Cities of Minnesota. Two largest cities in the state, they enhance your Midwest road trip with both urban and natural treasures.
The area ended up on our itinerary as a means to see one of the greatest natural sites in the U.S. It was Dylan’s idea to visit the Mississippi River, the second longest river in the country. You can see it from many places in both St. Paul and Minneapolis. The most beautiful views of the river and St. Anthony Falls, however, open up from the Stone Arch Bridge.
From here, you can also see the Mill City Ruins, historic remains of once large flour mills.
As the evening was approaching, we ventured to the greener side of Minneapolis to see Minnehaha Falls. A few hours later, we dropped off our rental car and boarded a return flight to Los Angeles. Our 4-day Chicago to Minneapolis road trip was officially over.
