10 Chill Road Trips From Chicago You Have to Take

As great as it is there are many reasons to take road trips from Chicago. 

Chicago is brimming with world-class museums, live music venues, fabulous events, and international cuisine. Which is more than enough to keep you busy for weeks! Pound for pound it stands up to New York City, and Los Angeles. And that’s saying a LOT!

Chicago is iconic, lively, and undoubtedly one of the best cities to visit in the United States.

However, there’s a whole world waiting to be discovered just beyond the city’s limits. Where will your road trip from Chicago take you?

10 Sweet and Easy Road Trips from Chicago

The state of Illinois (where Chicago lies) is bordered by four other states. Each one has something great to offer in the way of landscape, atmosphere, and culture. By visiting some of the surrounding areas you’ll have a much better understanding of the mid-west. As much as we love Chicago, we think it’s imperative that visitors take at least one road trip from Chicago!

Whether you want to escape the city for a day or plan a romantic weekend getaway from Chicago – we’re here to help. We’ve compiled a list of the best places to visit near Chicago to help you narrow down your options. From lakeside retreats to nature parks to lively cities – there’s a place on the list for everyone.

Most of the spots on this list deserve at least a day to visit, and some require more time. You’ll want to save an entire weekend for the trip. If you’re able to travel by car you’ll have much more freedom to explore. However, most of these places to visit near Chicago can be reached by train or bus as well.

Are you ready to delve into our list of the best road trips from Chicago? Let’s go!

Milwaukee, Wisconsin

If you’re looking for great weekend getaways from Chicago, then Milwaukee should definitely be top of your list. This charming city has been under the radar for years, but recently it’s become a popular travel destination. If you thought there was nothing worth seeing in Milwaukee, then you were mistaken! This southern city has a great nightlife scene, plenty of fab museums and gorgeous riverside walks to keep you busy.

Explore Milwaukee’s historic Third Ward, where you’ll find a lively atmosphere and some cool architecture. There are loads of warehouses and trendy lofts popping up throughout the area, as well as some awesome boutiques, bars, and restaurants.

Milwaukee is famous for its beer culture, so while you’re there you should definitely join a brewery tour. What could be better than exploring the city, getting to know the locals, and drinking delicious beers at the same time?

The city has been settled by immigrants from all over the world, a fact which is reflected in the huge variety of food it offers. Head to the Milwaukee public market to sample international cuisine as well as the mouth-watering local delicacy: cheese curds!

Once you’re done with all the eating and drinking, it’s time to get cultural! Be sure to check out the Public Museum, as well as the Milwaukee Art Museum to learn about the city and see some unforgettable works. Don’t forget about the Harley-Davidson Museum where you can get in touch with your inner biker, or simply admire the bikes from a distance.

If you’re planning a road trip from Chicago then Milwaukee is a great option. Food, beer, culture, and a vibrant atmosphere – this is a southwestern city with plenty to offer.

Lake Geneva, Wisconsin

Lake Geneva has a reputation for being one of the best places to visit near Chicago – and for good reason! This famous resort spot has been a popular retreat for Chicago locals and tourists forever. It’s where wealthy Chicagoans came to build their mansions during the Gilded Age – which you can still admire today! Of course, many of them don’t leave the comfort of their hotel and pool area.

However, Lake Geneva has plenty of great off-the-beaten-track spots to discover and explore – if you know where to look. Whether you prefer getting lost in the great outdoors or chatting to locals in a dive bar – Lake Geneva has something for everyone.

Walk the famous 26-mile Lake Geneva Shore Path, which is an old Native American trail that circles the entire lake. The mostly flat track offers stunning panoramas, wildlife, and lakeside architecture. There are plenty of fun outdoor activities to do in Lake Geneva to get your adrenaline pumping. Hiking, biking, ziplining, and more – Lake Geneva is the perfect spot to escape city life and reconnect with nature.

Wisconsin has a lively drinking culture, and Lake Geneva is no exception. When the evening sets in, duck inside a local dive bar for cheap booze, live music, and memorable chats with the regulars. There are plenty of lakeside restaurants serving international cuisine, as well as spots to gorge on a huge plate of BBQ ribs.

If you’re there in summer you’ll find beaches dotted all around the lake where you can relax and take a dip in the clear water. If you’d rather escape the crowds in Lake Geneva, then head over to nearby Lake Como or Lake Delavan, both quieter and more secluded spots. Plenty of nature, sun, and swimming spots make this area the ideal choice for a weekend getaway from Chicago.

Indiana Dunes, Indiana

Lengthy grasses, wildlife-filled marshes, and looming white pine forests fill the stretch of Lake Michigan shoreline at the Indiana Dunes National Park. If you love the outdoors then Indiana Dunes is the perfect road trip from Chicago.

Explore the rugged beaches and breathtaking (literally) hiking trails that zig-zag up the sand and through the charming woodlands. If you’ve got plenty of energy to burn then try the 3 Dune Challenge, a stunning 1.5-mile climb that takes you to the park’s highest dunes: Mt Jackson, Mt Holden and Mt Tom.

If you prefer more challenging activities, you’ll find plenty of options for biking, paddling, and winter snowshoeing. Get a breath of fresh air in one of the best places to visit near Chicago.

Starved Rock State Park, Illinois

Just a 2-hour car ride from downtown Chicago is Starved Rock State Park. If you love the city but find yourself pining for nature then this is one of the best road trips from Chicago.

There are plenty of things to do in the park, like kayaking, rafting, horse riding, and lots and lots of hiking. Explore the park’s 15 canyons, all of which offer stunning views of the Illinois River, and the surrounding flatlands and farmlands. The park is bustling with wildlife, and if you visit in winter you might be lucky enough to spot some nesting bald eagles. Lush greenery, stunning vistas, and endless spots to explore make this one of the best natural areas near Chicago.

The trails can get slippery at times, so be sure to dress in appropriate clothes and wear good hiking boots. Once you’ve got your fill of the outdoors and have worked up a good appetite head to the park’s lodge where you’ll find a restaurant and bar area.

Indianapolis, Indiana

Indiana’s state capital Indianapolis is a great weekend getaway from Chicago, with something for everyone to enjoy. Filled with trendy districts, hipster cafes, and fab art – affectionately named “Indy” is a vibrant city with a lot to offer. Home of famous American novelist Kurt Vonnegut you’ll find a gigantic 38-foot-high mural of him on Massachusetts Ave.

A fantastic walking and biking trail connects the entire city, and we recommend using it as a base for exploring all the best spots. The Indy Cultural Trail is the 8-mile urban track connecting all six of the city’s downtown cultural districts. Work your way through Mass Ave, Fountain Square, Indiana Avenue, Canal & White River State Park, and the Wholesale District. Discovering a new city is always better when you can take your time and stumble upon hidden gems along the way, right?

Begin your Indianapolis journey in one of the city’s coolest neighborhoods: Massachusetts Avenue. In the city’s original arts and culture district, there are plenty of indie stores, great restaurants, lively bars, and awesome art to spot. Be sure to check out Newfields (Indianapolis Museum of Art). The expansive museum features indoor galleries, as well as outdoor gardens and artworks. Visit the historic City Market which was opened in 1886 and houses over 30 locally-owned artisan shops selling food, drink, and handmade gifts.

From wandering the banks of pretty canals to sipping beer in a brewery to chowing down on all the delicious fare that Indy has to offer – you’re in for a treat.

Madison, Wisconsin

Just 3 hours away by car, Madison is one of the best road trips from Chicago destinations. Madison is a big-time college town located in Wisconsin. With its thriving student population, numerous breweries, and a plentitude of cheese. You’re sorted if partying, eating, and drinking is your forte. With 2 great lakes, fantastic outdoor opportunities, and a vibrant art scene – Madison is certainly worth a visit.

One of the best things about Madison is how bike-friendly it is! Explore the city on two wheels by renting a bike at one of the numerous rental stores in the city. Being bike-friendly isn’t the only progressive thing about Madison. The city is known for being super inclusive and forward-thinking – a fact that is heavily reflected in the city’s music and arts scene.

Stroll down State Street where you’ll find an eclectic mix of trendy cafes, bohemian shops, bookstores, and food carts. There are plenty of museums to explore too including the Madison Museum of Contemporary Art (MMOCA), Wisconsin Historical Museum, and even the National Mustard Museum. Yes, you read that correctly. A museum dedicated to mustard. Be sure to visit the gorgeous Capitol building, which has been standing since 1907. You can visit the building as part of a free guided tour, or explore by yourself.

Madison is home to some 40,000 college students throughout the year, so there are plenty of opportunities to catch a concert. Check out the schedule at The Majestic Theater for national artists and local bands. Smaller venues like Sylvee and High Noon Saloon offer more intimate concerts and live music, which is a great way to spend a Saturday night in Madison.

Oak Park, Illinois

Once home to legendary architect Frank Lloyd Wright, Oak Park is a charming leafy Chicago suburb that’s definitely worth a visit. Just a 25-minute train ride from downtown, Oak Park is the perfect spot if you’re looking for great road trips from Chicago.

Frank Lloyd Wright lived in Oak Park for 20 years and developed his famous Prairie style in his home and studio there. You can take a two-hour tour through the Frank Lloyd Wright Trust, which has 10 stops and allows plenty of time to gawp in wonder at the beautiful architecture. Visit his home and studio, as well as Unity Temple which was recently named a world heritage site. If you’re an architecture lover then Oak Park is one of the places to visit near Chicago that you can’t miss!

Frank Lloyd Wright wasn’t the only famous Oak Park local. Ernest Hemingway is the town’s other notable son. He was born in an imposing Victorian home just a few blocks from Wright’s birthplace. Now the house is the Hemingway Birthplace Museum, where you can learn about the modernist writer’s formative years.

Oak Park also offers plenty of great spots to eat and drink after a day of exploring. Check out the Kingslahger Brewing Company and sample some delicious local brews. The charming neighborhood provides a great weekend getaway from Chicago and the chaos of the city.

Holland, Michigan

If you love small towns with a European feel, then Holland Michigan is one of the best road trips from Chicago. As its name suggests, Holland was founded by Dutch Calvinists separatists escaping from persecution in the Netherlands. It’s been called one of America’s prettiest towns, a sentiment which is particularly applicable when the annual May Tulip Time Festival takes place and the city is covered in brightly colored flowers.

Holland is located on the shores of two lakes – Lake Michigan and Lake Macatawa. There are plenty of sandy spots to relax before taking a dip in the clear waters. Immerse yourself in the town’s Dutch heritage by visiting the 251-year-old windmill De Zwaan. Be sure to Nelis’ Dutch Village where you can explore the 10 acres of this “authentic” Dutch village led by a guide in traditional Dutch costume. After a day of exploring you’ll be ready to eat, and one of the lakefront restaurants is the perfect place to end a wonderful day.

Holland oozes small-town charm and is one of the best places to visit near Chicago to escape the big city and unwind.

New Glarus, Wisconsin

Another small town brimming with European heritage, New Glarus is one of the best road trips from Chicago if you want some peace and quiet. Located in Wisconsin, it’s a 2.5-hour drive from downtown Chicago.

New Glarus was named after Glarus, a township, located in Switzerland. The quaint town was founded by immigrants from the Swiss town in the late mid-19th century. The town reflects its Swiss heritage with charming architecture resembling that in Switzerland, restaurants serving authentic Swiss food, and shops where you can get traditional Swiss gifts. Today, America’s “Little Switzerland”, thrives with a close-knit community of businessmen and artists that celebrate Swiss culture and tradition.

Visit the Swiss Historical Village to get a taste for what life was like when the Swiss settlers came. Then pop into the Chalet of the Golden Fleece Museum where you can view a unique collection of weird and wonderful items including jewelry that belonged to a Mexican empress, to historic 16th-century tapestries.

After you’ve learned all about New Glarus it’ll be time for a refreshing beer at the New Glarus Brewing Company. Then head to Glarner Stube, a popular Swiss-German restaurant that’s popular with locals and serves authentic European food. Try the mouth-watering hand dipped cheese curds!

Transport yourself to Switzerland by visiting New Glarus – one of the best places to visit near Chicago!

Detroit, Michigan

Detroit is a bit further afield than the other spots on our list, but if you’ve got the time and a good driving playlist then it’s definitely worth visiting as a weekend getaway from Chicago.

After decades of neglect, in recent years Detroit has undergone a renaissance and is no longer held at arm’s length by Michigan tourists. Although there are still sketchy areas of the city (like most cities in the world), Detroit breathes new life and thrives with art, music, sport, and nightlife. Young and innovative people have transformed many of the city’s previously abandoned spaces into cafes, trendy galleries, and distilleries. Birthplace of the automobile, home to Motown, and buzzing with breweries and eateries – Detroit will have something that captures your interest.

Marvel at downtown’s art deco skyscrapers, discover the city’s tranquil parks and spot some edgy street art along the way. Visit the Detroit Institute of Arts to see some of the best art in the city. It’s also where you’ll find the famous Detroit Industry Murals by Mexican artist Diego Rivera (Frida Kahlo’s husband) which depicts industry at the Ford Motor Company.

There’s plenty of outdoor art to discover in Detroit, with installations in parks and street art hidden around every corner.

Be sure to check out the City Market, where you’ll find a range of fresh produce, great coffee, and street food stalls. When the sun begins to set head to Belle Isle, an island in the middle of the Detroit River, to snap the quintessential Detroit sunset photo.

Detroit’s music scene is nothing short of fantastic. Whether you’re into jazz, blues, rock, or pop – Detroit has it all. From intimate gigs in dive bars to jazz sessions in moodily lit clubs to international concerts – your live music needs will be more than satisfied.

Like This Article? Pin It!