If you live in Chicago and want to get out of the city, or if you just want to visit the windy city and take a few trips, there are many ways to get around by car.

Located on the shores of Lake Michigan, with the Great Lakes and neighboring states within easy reach, there is every reason to take your car and explore the area.

With city trips, small coastal ports, excellent natural parks and the occasional winery and brewery, these are our top 20 road trips from Chicago.

20 Best Road Trips From Chicago

Daytime driving from Chicago

1. Milwaukee, Wisconsin

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

20 Best Road Trips From Chicago

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A quick trip from Chicago to Milwaukee takes you north on the I-94 to the point where three different rivers (Milwaukee, Menomoni and Kinnikinnik) meet and flow into Lake Michigan.

You can easily visit Milwaukee Day and see the beautiful architecture and Harley-Davidson Museum, where you can learn the history of the infamous motorcycle brand and try out a scary realistic simulator.

However, to get the most out of it, you should really consider spending the night in a hotel and exploring the local beer scene. Milwaukee, the town where Miller, a large brewery, is located, is best known for its large selection of microbreweries and small producers of quality beer.

Try the City Lights Brewery, located in the renovated 1902 Milwaukee Gas Light buildings, offering a fresh industrial atmosphere with a mix of old and new.

Distance from Chicago: 93 miles (1 hour 30 minutes)

When to visit: From June to September to take advantage of the best weather.

2. Port State, Michigan

Harbor Country is one of the most popular destinations for Chicago residents. This idyllic southwestern coastline of Michigan stretches from the border with Indiana to the city of Sawyer.

20 Best Road Trips From Chicago

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Originally, this very rural area of Michigan, with several small towns and associated lakeside harbors, was a popular tourist destination.

You’ll find great restaurants and interesting art galleries and independent craft shops along the coast – New Buffalo is great for its boutiques and courtyard shops.

There are also a number of very solid vineyards in the region. Julian Winery of Lemon Creek is a great place to visit and is located near the Interstate.

With its crafts, relaxed country life and outdoor activities on and around the lake, Harbor Country is the perfect antidote to the hustle and bustle of the city.

Distance from Chicago: 80 miles (1 hour 20 minutes)

When to visit: August and September to make the most of the cellar and the weather.

3. Fenneville, Michigan

If you visit the coast of Michigan, you will reach Fennville, a small town in Allegan County in the Michigan Agricultural Belt.

20 Best Road Trips From Chicago

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Fenneville has original local museums and attractions. One of them is the Children’s Museum of Eternal Curiosity, a non-profit organization created to inspire children of all ages to learn. The exhibitions are very interactive and fun for the whole family.

Outside the centre of Fennville you will find carousel fields and orchards that are beautiful and produce delicious dishes. Stop by the Crane Garden to enjoy one of their legendary cakes while you’re on your way!

On the way to Lake Michigan you will see the small harbour village of Saugatuk. There is a large white sandy beach and you can walk along the promenade, watch the passage of the locals’ boats or explore the shops along the quays.

Distance from Chicago: 145 miles (2 hours 20 minutes)

When to visit: From June to September for summer happiness

4. Rockford, Illinois

Because of its forests and green rivers, Rockford is called the Forest City and is also known as the spiral capital of the world. The self-proclaimed nickname comes from the factories in the city that supply the rest of the country with various types of fasteners, screws, nuts and bolts.

20 Best Road Trips From Chicago

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Rockford is the largest city in Illinois outside Chicagoland (Chicago area). You can easily commute there for a day or stay overnight to see other local attractions and museums.

Rockford lives up to its main nickname, as there are many outdoor spaces to explore – Anderson Japanese Gardens, Clemus Botanical Gardens and Rock Kat State Park – all within the metropolis.

One of the interesting places to visit is the house of Laurent Frank Lloyd Wright. 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 design and accessibility – the views are incredibly modern, despite the fact that some 70 years have passed!

Distance from Chicago: 88 miles (1 hour 30 minutes)

Visiting hours: June-August

5. Lake Geneva, Wisconsin

You may not have heard of it, but the United States has its own Lake Guevena, and it’s in Wisconsin, right on the border with Illinois.

20 Best Road Trips From Chicago

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The inhabitants have not stopped giving the lake the name of a slightly more famous lake in Switzerland. The city at the western end is called Lake Geneva, the lake in the north is called Lake Como, on the shores of which the city of Como lies.

Welcome to the Alps of Wisconsin!

Local skiing may be limited, but there is plenty to see and do around Lake Geneva. The main attraction is the 21 mile circular walk around the lake, with breathtaking forest scenery and stunning views of the water.

You will pass impressive houses and quiet lake blocks with picturesque cafes. If 21 miles seems a little too much for you, concentrate on the 2 mile section of the West End.

On the south shore of the lake lies Black Point Manor. It is a large historic mansion built in 1888 by Chicago beer magnate Conrad Seip. You can visit the country house and explore the vast grounds, including 620 feet of coastline.

Distance from Chicago: 83 miles (1 hour 35 minutes)

When to visit: The best of spring and summer

6. Oglesby and Utica, Illinois

The small town of Oglesby, with 3,600 inhabitants, is famous for its natural beauty. Nestled in the bend of the Vermillion River, Oglesby and his neighbour Utica are ideal for exploring some of the best outdoor locations in Illinois.

20 Best Road Trips From Chicago

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The main attractions are two large parks – Hungry Rock State Park and Mattissen State Park.

Although the two parks are not as big as the others, there are many interesting things to discover, with paths leading through the ravines and some amazing rock formations.

You can easily take a day trip from Chicago, but if you decide to go there for the weekend, you can stay at the Starved Rock State Park Lodge, which has a swimming pool and a spa to relax after your walk.

Make sure you have something to eat at the Rothbie booth. This fast food classic, Mom n pop, has been based in Oglesbee since 1955 and serves first class root beer floats and hamburgers.

Distance from Chicago: 100 miles (1 hour 30 minutes)

When to visit: Best weather from May to September

Weekend trips from Chicago

7. Grand Rapids, Michigan

Grand Rapids is Michigan’s second largest city after Detroit and in recent years has become famous for its cool and hip atmosphere.

20 Best Road Trips From Chicago

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Several museums and attractions are worth a visit – the Grand Rapids Public Museum and the Art Museum. Alternatives are the Frederick Meyer Sculpture Park and the Fish ladder.

But the best thing about Grand Rapids is the food and drink. Restaurants like Grove and Terra serve locally produced ingredients, which means that the menu changes all year round. A wide range of breweries consists of European-style beer and Harmony Pizzeria.

You can make the round trip in one day, but it can take up to 3 hours one way from Chicago. So do it at the weekend and add a few stops at Fenneville and Harbor Country (see the two above).

Distance from Chicago: 186 miles (2 hours 45 minutes)

When to visit: Best weather from June to August

8. New Glarus, Wisconsin

Some of the upcoming options are on our list of trips to North Wisconsin. First the village of New Glarus. It was founded in 1845 by a group of Swiss settlers from the Swiss canton of Glar.

20 Best Road Trips From Chicago

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If you get to New Glar, they’ll forgive you if you think you’ve been teleported to Central Europe. Everything here looks, smells and smells like Switzerland.

The Historic Village of Switzerland is a large living museum with 14 buildings in the style of an original 19th century settlement. You can see how every aspect of village life would be complemented by a forge, a school and church buildings.

You should try the Glarner Stube restaurant in town. Despite the fact that there are many dishes to the taste of American tourists, you can try the Venerschnitzel (fried veal cutlet) or the cheese fondue (slices of bread dipped in melted cheese).

Cheese fondue is at the top of our list of the best products in the world!

Distance from Chicago: 145 miles (2 hours 40 minutes)

When to visit: From May to September, for better weather or to enjoy the alpine experience during the winter months.

9. Monroe, Wisconsin

The city of Monroe is about 20 kilometers south of New Glarus and a little closer to Chicago. If you want to make the most of your Swiss experience, combine your trip to New Glarus with a stop in Monroe, the American capital of Swiss cheese.

20 Best Road Trips From Chicago

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It’s all about cheese. You can take part in a cheese route, visit cheese tastings, meet local cheese producers and eat any cheese dish in the sun.

If you want to test your feelings: Limburger is the title of the most terribly smelly cheese in the world and is only produced in Monroe. The smell is so bad that the US Postal Service has banned the Limburger because of the stench.

Otherwise you will find a selection of different cheeses and varieties. Everything is used – from cow’s, goat’s and sheep’s milk to imitations of European cheeses and unique local flavours.

If you’ve eaten enough cheese, you can mountain bike on a network of trails around Monroe. It’s called – you guessed it – Cheese Country Trail!

Distance from Chicago: 130 miles (2 hours 20 minutes)

When to visit: Best weather from June to September

10. Madison, Wisconsin

The capital of Wisconsin is often neglected in favor of his big brother Milwaukee, 80 miles to the east.

20 Best Road Trips From Chicago

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The trendy city has a lot to see and do. There are two enormous lakes on either side of the city centre, creating a unique relaxed atmosphere. There are a dozen other small lakes with dots that divide the city into smaller areas and give it a lot of character.

The Capitoline building and several large museums are well worth a visit – the Madison Museum of Modern Art and the Chasen Art Museum have huge collections covering different styles and periods.

The best thing about Madison, like so many places in Wisconsin, is the food. There are festivals all year round, from the world’s largest roasting festival (you can eat lots of sausages here!) to the Bacon and Brews event, where you can enjoy delicious bacon-and-beer couples, there’s always something going on.

Distance from Chicago: .147 miles (2 hours 30 minutes)

Visiting hours: May-September

11. The Netherlands, Michigan

The city of Holland lies on the length of Lake Maccata, which flows into Lake Michigan. The name says that everything here revolves around the Dutch origin.

20 Best Road Trips From Chicago

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The city moved the 250 year old windmill from the Netherlands to the Netherlands and established it on its own island, which is now called Windmill Island. It is the only working Dutch windmill in the United States, and it is beautiful in May, when the weather is nice and thousands of tulips are in bloom.

If an authentic windmill and tulip fields are not Dutch enough, there is an entire Dutch village to visit. The village has a historic view over the Dutch villages and you can even visit a clog factory.

The inhabitants of the Dutch village wear traditional clothing, play Dutch music and you can take part in one of the mass dances if you wish.

There are many activities for children – special attractions and a zoo for pets. So bring your family and enjoy a great weekend away!

Distance from Chicago: 155 miles (2 hours and 30 minutes)

When to visit: May for the tulip flower

12. Sedarburg, Wisconsin

A little further north of Chicago than Milwaukee is the city of Chederburg. Named after the great cedars, it is best known for the lush forests that cover the hills around Sedarburg.

20 Best Road Trips From Chicago

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You can come to Kederburg for a long day, but it really is the perfect place to relax at the weekend.

As everywhere in Wisconsin, food and drink are the focus of attention. The local brewery Fermentorium offers about 24 different beers – not too poor for the place!

You can also visit the Cedar Creek Winery and taste local wines that might just surprise you. And the view from the vineyard is beautiful!

September and October are the best times to come to Sedarburg: The trees sparkle with oranges and burgundy, while locals celebrate Oktoberfest with special events, seasonal beers and delicious food.

Distance from Chicago: 112 miles (2 hours)

When to visit: Come in autumn to see the incredible shades of gold and red on the leaves.

13. Dunes Indiana, Indiana

One hour from downtown Chicago, the Indiana Dunes became the newest national park in the United States in 2019.

20 Best Road Trips From Chicago

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It’s easy to get from Chicago in a day trip, but if you want to explore other routes and escape the daily grind, a weekend trip can be more efficient, even if you’re so close.

The dunes stretch for 15 miles across Lake Michigan, and the national park is adjacent to the state park of the same name. The three highest sand dunes are in State Park and the highest, Mount Tom, is 192 feet.

There are several routes that take you up and down the dunes, through groups of trees overgrown by sand, dunes and pine forests.

Because there is a lot of water fun on the lake, the parking spaces can fill up quickly, so make sure you come here in the morning to get a spot.

Distance from Chicago: 50 miles (1 hour)

When to visit: Summer for hiking or winter for cross-country skiing and snowshoeing!

14. Photo CD in Wisconsin Dells, Wisconsin

Wisconsin Dells is known for two things: the picturesque gorge of the Wisconsin River and the many water parks that have earned the city the nickname Peace Water Park Capital.

20 Best Road Trips From Chicago

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Although many people come to Wisconsin Dells to visit a water park, don’t forget to take a tour of the Wisconsin River Gorge.

The Dells boat trips take you through narrow river passages – these Dells are gorges through layered rock formations that turn into small high islands as the river widens.

There are 4 large water parks (Kalahari, Big Wolf, Chula Vista and Wilderness) and a total of about 20 stations, with more under construction. Many of them are built indoors, so you can swim, relax and get off the crazy slides at the weekend when everything on the road is frozen!

Distance from Chicago: 195 miles (3 hours)

When to visit: Summer, to make the most of the river, but all year round for covered water parks.

Weekly trips by car from Chicago and longer trips

15. Detroit, Michigan

Motor City is after Chicago the biggest city in the Midwest and is worth the trip.

20 Best Road Trips From Chicago

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After a period of rapid growth in the first two thirds of the 20th century, the company is now in the middle of a new era. From the 1970s Detroit experienced an economic collapse and a huge recession.

Car production shifted to other cities in the United States, factories in Asia and Mexico, and large parts of Detroit became ghosts of their own past.

Today the city is in the midst of reconstruction, as the centre of Detroit becomes increasingly fashionable and lively, as old dilapidated factory buildings are gradually rebuilt or replaced by new buildings.

Be sure to visit the Heidelberg Project – this outdoor art installation uses life-saving materials to draw attention to Detroit’s plight and the current period of change through noisy modern sculptures.

The classic city of Ann Arbor is an ideal stopover on your way. This campus offers classical architecture, art galleries and large, small cafes where you can relax or have a bite to eat.

Distance from Chicago: .290 miles (4 hours 20 minutes)

When to visit: It’s worth a walk all year round…

16. Disk along the upper course of the Mississippi

The Great River Route runs along the Mississippi, and part of it can be reached via Chicago Scenic Drive.

20 Best Road Trips From Chicago

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You can reach the river in Savannah or a little further in Clinton, depending on the route you choose.

The route then follows the river to the north – you can cross from Iowa and then Minnesota from Illinois and Wisconsin, as the river continues to form the state border along this passage.

Follow the Grand Fleuve road through the bends and curves and you will be rewarded with stunning views across the entire road. There are many places to stop and many parks and footpaths if you want to get out of the car.

The route to La Crosse passes several excellent stops – look out for the Black Hawk Bridge over the Mississippi River at Lansing and some of the best panoramic views of the river and surrounding forests at Nelson Dewey State Park.

Distance from Chicago: .300 miles (6 hours)

When to visit: Go out in the summer because of the weather and walking possibilities.

17. Louisville, Kentucky

To get from Chicago to Louisville, you have to drive all the way to Indiana to the Ohio – St. Louis River. Louis is across the John F. Kennedy Memorial Bridge.

20 Best Road Trips From Chicago

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Louisville is best known as the owner of the Kentucky Derby – the famous races take place on the first Saturday of May and have been held since 1875. If you don’t come to Derby, you better not go in May, because hundreds of thousands of people are coming to the event and prices are rising.

Louisville, founded in 1778, is an amazing combination of old and new. The classic design may look more like a city on the east coast, where Louisville has the second largest number of cast-iron facades after New York, especially in the main western area.

There are several museums that are worth visiting – some of the most important are along the Museumstraat. The Mohammed Ali Centre in Louisville and the Fraser Museum of History will take you there!

Be sure to visit the Slugger museum and the factory – this baseball bat manufacturer offers guided tours where you can see the whole process. On the side of the building is an exact scale replica of Babe Ruth’s Louisville Slugger baseball bat, although it is slightly longer at 120 feet.

Distance from Chicago: .300 miles (4 hours and 30 minutes)

When to visit: It works well all year round – avoid crowds and high prices in May.

18. Full circle from Lake Michigan to Makinak Island

It’s a trip that will show the best of Lake Michigan – a complete naval tour with a trip to Makinak Island in the opposite corner for the return trip.

20 Best Road Trips From Chicago

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To get the most out of your trip, take a few weeks and make many stops along the way. You will pass through the cities of Milwaukee, Green Bay, Traverse City and Grand Rapids, which are all worth a trip on their own.

Then there are dozens of beautiful natural parks worth exploring, especially in the direction of the northern tip of the lake. In addition, the city has beautiful beaches, several large sand dunes, including Indiana Dune National Park, and beautiful port cities.

Once you’re halfway there, you should spend a day or more on the island of Makinak.

You cannot take the car to Mackinac – you must park the car in one of the designated car parks and drive through it. Fast ferries get you there in less than 20 minutes.

There are no cars on the island and you can walk, visit the lighthouses and walk to the Arc Rock on the east side of the island.

Distance from Chicago: 430 miles (6 hours 30 minutes) clockwise around Lake Michigan, 455 miles (7 hours 30 minutes) clockwise.

When to visit: In summer, to ensure that the roads and railways are open, and the Mackinac ferry service is only available during the summer months.

19th St. Louis, Missouri.

No, it’s not a typo – it’s the third destination on our list of destinations in Chicago, which is exactly 300 miles away! It’s very easy to get to St. John’s, Newfoundland. Louis – the I-55 will take you to Gateway City.

20 Best Road Trips From Chicago

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As you approach St. John’s In St. Louis you’ll see the city’s first and most important attraction – a huge steel doorway arch 630 feet high. To get a great view of the city, you have to go upstairs – tickets cost $14 for adults and $11 for kids with weekend discounts.

Beer and baseball are two things the city is particularly famous for. The Anheuser-Busch Brewery and the Biergarten Brewery are home to the Budweiser, but there are many small local breweries where you can enjoy a more authentic experience.

When the cardinals at St. John’s play… In St. Louis, it’s worth going if you can get (expensive) tickets – it’s one of the most successful baseball teams of all time, and baseball is the number one sport in the city.

Don’t forget to go to certain concert halls. From jazz to soul, St. John’s St. Louis was one of the most famous cities in the United States in the field of music – that’s where Tina Turner and Scott Joplin, among others, started their careers.

Distance from Chicago: 300 miles (4 hours 20 minutes)

When to visit: Works well all year round, but chooses the summer for musical events and the baseball season.

20. Minneapolis, Minnesota

You may not have thought of Minneapolis as a Chicago vacation destination, but Minnesota’s largest city is an amazing combination of culture, music, great food and outdoor activities that you really should visit.

20 Best Road Trips From Chicago

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Minneapolis is located on both sides of the Mississippi and has more than a dozen lakes within the city limits creating an amazing landscape. In St. Paul, these two metro zones together are known as Twin Cities and are among the largest in the Midwest.

The City of Lakes is a dynamic center of activity – 6 of the Fortune 500 companies are located here and are known as an important cultural and artistic center.

Don’t forget that Minneapolis can be cold in the summer, even ice-cold. Winters are very cold and snowy – a trip from Chicago in mid-February might not be the best idea!

The quickest route from Chicago to Minneapolis is via the I-90 and I-94 through Wisconsin. If you want to enjoy the best scenery, you can always cross the Mississippi and take the Great River Road (see #16 above).

The detour takes about two and a half hours. So plan a stop along the way.

Distance from Chicago: .410 miles (6 hours)

When to visit: From June to August to take advantage of the summer weather.

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