Panoramic view of State Harbor Marina on Mackinac Island, Michigan
Ricardo Reitmeyer/

20 Best Road Trips From Chicago

By Sasha Yanshin | Updated on 20 June 2020

If you live in Chicago and want to get out of the city or you're just visiting the Windy City and want to make a few drives out, there is a lot of road trip options.

Sitting right on Lake Michigan with the Great Lakes and a number of surrounding states within easy reach, there is every reason to get in the car and explore.

Featuring city breaks, small coastal harbor towns, outstanding natural parks and the occasional wineries and breweries, here are our 20 best road trips from Chicago ordered from closest to furthest away - make sure to read further down for more epic road trip itineraries!

1. Indiana Dunes, Indiana

1 hour from Chicago (50 miles)

Indiana sand dunes on the shoreline of Lake Michigan
Delmas Lehman/

Only an hour away from downtown Chicago, Indiana Dunes became the newest National Park in the United States in 2019.

You can easily visit on a short day road trip from Chicago, but if you want to explore the different trails and get away from it all, a weekend trip might work better despite being so close.

The dunes stretch along a 15-mile stretch of Lake Michigan and the National Park borders the State Park of the same name. The 3 tallest sand dunes are all in the State Park with the tallest, Mount Tom, standing at 192 ft.

There are a number of different trails that will take you up and down the dunes, past groups of trees that have been overcome by the sand, dune blowouts and pine forests.

With a lot of water activities on the lake, the parking lots can fill up quickly so make sure you get here in the morning to get a spot.

2. Harbor Country, Michigan

1 hour 20 minutes from Chicago (80 miles)

Sunset behind the Inner and Outer North Pier Lighthouses at St. Joseph, Michigan
Kenneth Keifer/

Harbor Country is one of the most popular getaway destinations for Chicagoans. This idyllic shoreline in Michigan's southwestern corner stretches from the Indiana border to the town of Sawyer.

Originally a very rural part of Michigan with a few small towns and their corresponding harbors on the lake, the area has grown into a popular tourist destination.

As a result, you will find some great restaurants and interesting art galleries and independent craft shops up and down the coast - New Buffalo is great for its boutiques and farm shops.

The area is also home to a number of very decent wineries. St Julian Winery or Lemon Creek are great to visit and well located just off the interstate.

With its artisan produce, a relaxed country vibe and outdoor activities on and off the lake, Harbor Country is a perfect antidote to the hustle and bustle of the city.

3. Milwaukee, Wisconsin

1 hour 30 minutes from Chicago (93 miles)

Skyline of downtown Milwaukee in the afternoon, Wisconsin, USA
Sean Pavone/

If there's one reason to visit Milwaukee, it is to see for yourself what the beer capital of the United States really looks like!

A quick road trip from Chicago to Milwaukee will take you north along the I-94 to the point where three separate rivers (Milwaukee, Menomonee and the Kinnickinnic) merge and flow into Lake Michigan.

You can easily visit Milwaukee for a day and see the beautiful architecture and the Harley-Davidson Museum where you can learn about the infamous motorcycle brand's history and have a go on a scarily realistic simulator.

To make the most of it, though, you really should consider stopping the night and exploring the local beer scene. Home to the huge Miller Brewing Company, Milwaukee is better known for having a huge selection of seriously good micro-breweries and small beer manufacturers.

Try the City Lights brewery tour - located in the renovated Milwaukee Gas Light Company buildings dating back to 1902, the brewery has a cool industrial vibe with its mix of old and new.

4. Rockford, Illinois

1 hour 30 minutes from Chicago (88 miles)

Water Powered Machine Shop replica in Rockford, Illinois

Nicknamed the Forest City due to the area's verdant woods and rivers, Rockford is also known as the Screw Capital of the World. The self proclaimed moniker comes from the factories in the city that supply the rest of the country with various kinds of fasteners, screws, nuts and bolts.

Rockford is the largest city in Illinois outside Chicagoland (the Chicago metropolitan area). You can easily visit for a day or stay the night to see more of the local sights and museums.

Rockford lives up to its main nickname with plenty of outdoor spaces to explore - the Anderson Japanese Gardens, Klehm Botanic Garden and the Rock Cut State Park are all within the metropolitan area.

One interesting place to visit is Frank Lloyd Wright's Laurent House. The famous architect built the house in 1951 and it is interesting to see how far ahead of its time it is in terms of its design and accessibility - the look is incredibly modern despite some 70 years passing!

5. Oglesby and Utica, Illinois

1 hour 30 minutes from Chicago (100 miles)

Illinois Canyon at dawn in the Starved Rock State Park, Illinois
Eddie J. Rodriquez/

The small town of Oglesby, home to 3,600 people, is renowned for its natural beauty. Oglesby and its neighbor Utica lie nestled into a curve of the Vermilion River and is perfect for exploring some of the best outdoors in Illinois.

The main attractions are the two major parks - the Starved Rock State Park and the Matthiessen State Park.

While both parks are not as large as some, there is plenty to explore with trails going through canyons and some amazing rock formations.

You can easily do a day trip from Chicago, but if you decide to come for the weekend, you can stay over at the Starved Rock State Park Lodge that comes complete with a pool and spa to unwind after your hiking.

Make sure you grab some food at the Root beer Stand. This Mom n pop classic fast food diner has been in Oglesby since 1955 and serves top notch root beer floats and burgers.

6. Lake Geneva, Wisconsin

1 hour 35 minutes from Chicago (83 miles)

Shoreline of Geneva Lake in Wisconsin with houses spread among trees
Thomas Barrat/

You might not have heard of it, but the United States has its very own Gevena Lake and it's located in Wisconsin, just across the border from Illinois.

The locals didn't stop at naming the lake after the slightly better known one in Switzerland. The town on its western end is called Lake Geneva, the lake just to the north is called Lake Como with the town of Como sitting along it.

Welcome to the Wisconsin Alps!

The local skiing may be limited, but there is a lot to see and do around Lake Geneva. The main attraction is a 21-mile loop around the lake with stunning forest scenery and great views of the water.

You will pass by some imposing homes and quiet lakeside neighborhoods with picturesque cafes. If 21 miles seems a little much, focus in on the 2-mile stretch on the West End.

On the south side of the lake is the Black Point Estate. It is a huge historic mansion built by Chicago beer tycoon Conrad Seipp in 1888. You can get a tour of the mansion and explore the vast grounds which include 620 feet of shoreline.

7. Cedarburg, Wisconsin

2 hours from Chicago (112 miles)

The old mill on water's edge in the fall in Cedarburg, Wisconsin
James Meyer/

A little further north from Chicago than Milwaukee is the town of Cedarburg. Named after the tall cedar trees, it is particularly well known for its lush forests that cover the hills around Cedarburg.

You could come to Cedarburg on a long day drive, but it's really perfect as a weekend getaway destination.

As with everywhere in Wisconsin, the food and drink scene takes center stage. The local Fermentorium brewery has some 24 different beers on tap - not too shabby for a local place!

You can also go on a tour of the Cedar Creek Winery and try the local wines which might just surprise you. Plus the views from the vineyard are sublime!

September and October are the best times to come to Cedarburg - the trees glow with their oranges and maroons and the locals celebrate Oktoberfest with special events, seasonal beers and great food.

8. Fennville, Michigan

2 hours 20 minutes from Chicago (145 miles)

Steps down to Lake Michigan in the fall in Fennville, Michigan

If you head further up the Michigan coast on a road trip around Lake Michigan from Chicago, you will get to Fennville - a small city in the Allegan County of Michigan's Agricultural Belt.

Fennville has a few quirky local museums and things to see. One is the Forever Curious Children's Museum - a non-profit organization created to spark a love for learning in kids of all ages. Exhibits are very interactive and fun for the whole family.

Outside of the downtown Fennville, you'll find rolling fields and orchards that are both pretty and make some great food. Stop at the Crane Orchards to sample one of their legendary pies as you make your way around!

Heading towards Lake Michigan, you will find the small harbor village of Saugatuck. Here you will find a great white sand beach and stroll along the boardwalk, watch local boats go by or explore the shops along the docks.

9. Monroe, Wisconsin

2 hours 20 minutes from Chicago (130 miles)

A street in Monroe - the Swiss Cheese Capital of the USA, Wisconsin
Sandra Foyt/

Around 20 miles south of New Glarus and a little closer to Chicago is the city of Monroe. If you want to maximize your Swiss experience, then combine your road trip to New Glarus with a stop in Monroe - the Swiss Cheese Capital of the USA.

Everything here is about cheese. You can go on cheese tours, go to cheese tasting venues, explore local cheese producers and eat every cheese-based dish under the sun.

If you want to test your senses, the Limburger cheese holds the title of the world's worst smelling cheese and is only made in Monroe. The smell is so bad, the United States Postal Service banned the posting of Limburger because of the stench.

Otherwise you can find a selection of different cheese styles and types. Everything from cow's milk to goat and sheep milk is used and there are imitations of European cheeses and unique local flavors available.

If you've had about enough of cheese, you can go on an ATV ride around the trail network around Monroe. It's called - you guessed it - the Cheese Country Trail System (no, really)!

10. Madison, Wisconsin

2 hours 30 minutes from Chicago (147 miles)

Skyline of downtown Madison with the Wisconsin State Capitol on Lake Monona
Sean Pavone/

The capital of Wisconsin is often overlooked in favor of its bigger brother Milwaukee 80 miles east.

The hip city has a lot of things to see and experience. There are two giant lakes right in the middle of the city, either side of downtown which creates a uniquely relaxed vibe. There's another dozen smaller lakes dotted around which breaks up the city into smaller neighborhoods and adds a lot of character.

The capitol building and a few great museums are definitely worth seeing - the Madison Museum of Contemporary Art and the Chazen Art Museum both have huge collections spanning different styles and time periods.

The best thing about Madison, like many places in Wisconsin, is the food. There are festivals throughout the year from the world's largest Bratfest (you can eat a lot of sausages here!) to the Bacon and Brews event where you can sample fine bacon and beer pairings, there is always something happening.

11. Holland, Michigan

2 hours 30 minutes from Chicago (155 miles)

Big Red Lighthouse where Lake Macatawa meets Lake Michigan in Holland, Michigan
Lonny Garris/

The town of Holland sits along the length of Lake Makcatawa that flows into Lake Michigan. The name gives away what this place is all about - everything here stems from Holland's Dutch origins.

The town transported a 250-year old windmill from the Netherlands to Holland and placed it on its very own island that is now called the Windmill Island. It is the only working Dutch windmill in the United States and it is beautiful in May when the weather gets good and the thousands of tulips flower.

If an authentic windmill and fields of tulips is not Dutch enough, there is an entire Dutch Village to go to. The village represents a historic view of Dutch settlements and you can even visit a wooden clog (shoe) making factory.

People in the Dutch Village wear traditional clothing, play Dutch music and you can join in one of the mass dances if you'd like.

There are a lot of activities for children - special rides and a petting zoo so bring the family and enjoy a great weekend out of the city!

12. New Glarus, Wisconsin

2 hours 40 minutes from Chicago (145 miles)

A traditional house with flowers in New Glarus, Wisconsin
John E Anderson/

A few of the upcoming options on our road trip list are all due north in Wisconsin. First is the village of New Glarus. It was founded by a group of Swiss settlers from the Swiss canton of Glarus in 1845.

You will be forgiven for thinking you were teleported to central Europe the moment you get to New Glarus. Everything here looks, feels, smells and tastes Swiss.

The Swiss Historical Village is a great live museum which has kept 14 buildings in the style of the original 19th century settlement. You can see how every aspect of the village life would have been complete with the blacksmith shop, school and church buildings.

You must try the Glarner Stube restaurant in town. Although it serves a lot of dishes to serve American tourist tastes, you can try the Wienerschnitzel (pan fried breaded veal cutlet) or the cheese fondue (dipping pieces of bread into molten cheese).

The cheese fondue is right up there on our list of the best foods in the world!

13. Grand Rapids, Michigan

2 hours 45 minutes from Chicago (186 miles)

View of downtown Grand Rapids, Michigan from the Grand River
Suzanne Tucker/

Grand Rapids is the second largest city in Michigan after Detroit and has gained notoriety for its cool vibe and hipster feel over the recent years.

There are a few museums and sights to see - the Grand Rapids Public Museum and the Art Museum are both worth going to. Alternative options are the Frederik Meijer Sculpture Park and the Fish Ladder Park.

The best thing about Grand Rapids, however, is the food and the drink. Restaurants like the Grove and Terra serve locally sourced ingredients which means the menu changes throughout the year. A wide selection of breweries includes European-style beers and the pizza-serving Harmony.

You could probably make the return trip in a day, but the journey can take up to 3 hours one way from Chicago so make it into a weekend and add a few stops at Fennville and the Harbor Country (see both above) on your way.

14. A scenic drive to Wisconsin Dells, Wisconsin

3 hours from Chicago (195 miles)

Wisconsin Dells sandstone formations in the Wisconsin River
Lorraine Swanson/

Wisconsin Dells is known for two things - its scenic Wisconsin River gorge and the high number of waterparks which has given the town its nickname as the Waterpark Capital of the World.

Although a lot of people will travel to Wisconsin Dells for the waterparks, don't forget to go on a tour down the Wisconsin River gorge.

The Dells Boat Tours will take you through the narrow river passages - these Dells are gorges through layered rock formations that become small tall islands as the river widens.

There are 4 large waterpark resorts (Kalahari, Great Wolf, Chula Vista and the Wilderness) and around 20 in total with more being constructed. A lot of these are built indoors so you can enjoy a weekend swimming, relaxing and going down crazy slides when everything outside is frozen!

15. St Louis, Missouri

4 hours 20 minutes from Chicago (300 miles)

St. Louis downtown in the evening with the Gateway Arch behind the Old Courthouse

No, it's not a typo - this is the third destination on our list of road trips from Chicago that is exactly 300 miles away! Getting to St Louis is easy - the I-55 will take you all the way to the Gateway City.

As you approach St Louis, you will see the first and main sight in the city - the huge 630-foot tall steel Gateway Arch. You should ride to the top of it to get unbelievable views of the city below - tickets are $14 for adults and $11 for children with discounts outside weekends.

Beer and baseball are the two things the city is particularly known for. The Anheuser-Busch Brewery and Biergarten are the home of Budweiser but there are loads of small local breweries where you will get a more authentic experience.

If St Louis Cardinals are playing, it's worth going if you can get your hands on some (expensive) tickets - they are one of the most successful baseball teams of all time and baseball is the number one sport in town.

Make sure you check out a few live music venues. From jazz to soul, St Louis has been one of the most prominent musical cities in the US - Tina Turner and Scott Joplin started their careers here among others.

16. Detroit, Michigan

4 hours 20 minutes from Chicago (290 miles)

A street in downtown Detroit with the Renaissance Center and the People Mover monorail

Motor City is the second largest city in the Midwest after Chicago and is worth making the drive for.

After a rapid period of growth through the first two thirds of the 20th century, Detroit suffered an economic collapse and a massive decline since the 70s.

Car production moved to other cities in the US, factories in Asia and Mexico and large blocks of Detroit became ghosts of their own past.

Today the city is undergoing a massive regeneration effort - downtown Detroit is becoming more hip and vibrant and one by one, the delapidated old factory buildings are being converted or replaced by new structures.

Make sure you visit the Heidelberg project - the outdoor art installation uses salvage materials to highlight the plight of Detroit and its ongoing period of change through loud modern sculpture.

The classic town of Ann Arbor is a great stop on your way - this university town has classic architecture, art galleries and great small coffee shops for you to relax or grab some lunch.

17. Louisville, Kentucky

4 hours 30 minutes from Chicago (300 miles)

The old City Hall at night  in downtown Louisville, Kentucky

To get to Louisville from Chicago, you will need to drive the length of Indiana until you reach the Ohio River - St Louis is right across the John F. Kennedy Memorial Bridge.

Louisville is best known as the host of the Kentucky Derby - the famous horse race takes place on the first Saturday in May and has run since 1875. If you're not visiting for the Derby, it's best to avoid going in May as hundreds of thousands come for the event and prices go sky high.

Founded in 1778, Louisville is a really amazing mix of old and new. The classic design may look more like an East Coast city with Louisville having the second highest number of cast iron fa├žades after New York, primarily in its West Main District.

There are a number of museums to explore - some of the main ones located along the Museum Row. The Louisville Muhammad Ali Center and the Frazier History Museum will keep you busy!

Make sure you visit the Slugger Museum and Factory - this baseball bat manufacturer has tours where you can see the whole process and the side of the building has an exact scale replica of the Babe Ruth's Louisville Slugger bat, albeit a little larger at a length of 120 feet.

18. A drive along upper Mississippi

6 hours from Chicago (300 miles)

Mississippi River running between Wisconsin and Minnesota near La Crosse

The Great River Road runs the length of the Mississippi river and you can drive part of it on a scenic road trip from Chicago.

You can join the river at Savanna or a little further down at Clinton depending on the route you take.

The route then follows the river north - you can cross in and out of Iowa and then Minnesota from Illinois and Wisconsin as the river continues to be the state border along the length of this drive.

Follow the Great River Road as it twists and turns and you will be rewarded with great views the entire way. There are plenty of places to stop and a lot of parks and trails if you want to get out of the car.

The route up to La Crosse will pass a few great stop off points - check out the steel Black Hawk Bridge over the Mississippi at Lansing and the Nelson Dewey State Park has some of the best panoramic views of the river and surrounding forests.

19. Minneapolis, Minnesota

6 hours from Chicago (410 miles)

Downtown Minneapolis, Minnesota in the evening as seen from the Stone Arch Bridge

You might not have thought of Minneapolis as a city break destination from Chicago, but Minnesota's largest city is an amazing mix of culture, music, awesome food and the outdoors which you really have to visit.

Minneapolis straddles both sides of the Mississippi and has over a dozen lakes within it's city limits which makes for amazing scenery. Combined with St Paul, the two merged metro areas are known as the Twin Cities and are one of the largest in the Midwest.

The City of Lakes is a bustling hub of activity - 6 of the Fortune 500 companies are headquartered here and it's known as a major cultural and arts center.

Remember that Minneapolis can get cold, and even feel cool in the summer. Winters are bitterly cold and very snowy - that drive from Chicago might not be the best idea in the middle of February!

The fastest way to get to Minneapolis from Chicago is to go the I-90 and I-94 route across Wisconsin. If you want to get better scenery, you can always cut across to the Mississippi and drive up the Great River Road (see #18 above).

The detour will add around two and a half hours so bake that into your planning and consider stops along the way.

20. A complete circle of Lake Michigan to Mackinac Island

6 hours 30 minutes from Chicago (430 miles)

Picturesque path down to the State Harbor Marina on Mackinac Island, Michigan
Gary Richard Ennis/

This is a trip that will show off the best of what Lake Michigan has to offer - a complete circle of the lake, heading to Mackinac Island on the opposite corner before making the return trip.

To make the most of the trip, take a couple of weeks and make a lot of stops along the way. You will pass through the cities of Milwaukee, Green Bay, Traverse City and Grand Rapids which are all worth going to in their own right.

Then there's dozens of amazing natural parks to explore, especially towards the northern tip of the lake. Add in beautiful beaches all over, some big sand dunes, including the Indiana Dunes National Park and the pretty towns of Harbor Country.

Once you get to halfway point, you should spend a day or longer on Mackinac Island.

You can't take your car with you to Mackinac - you'll have to park it at one of the designated ferry parking lots and make your way across. The fast ferries will take under 20 minutes to get you there.

With no cars on the island and a super relaxed vibe, you can take strolls, visit lighthouses and hike to see the Arch Rock on the east side of the island.

READ MORE - Road trip from Chicago To Mackinac Island

Longer road trips from Chicago

For those who want to go on a longer road, trip, the options above may not quite cut it so here are some longer routes that you might like the sound of: