Best Road Trips from Chicago

Lake Geneva is barely 90 miles from Chicago and can be easily accessed on a 90-minute car drive. This lake town is a pretty popular getaway for Chicago residents or for any outsider who wants to explore beyond the city limits. This city is located in the Southeast Wisconsin and is known for the famous Geneva Lake Shore Path which is open for public. It is great for sightseeing and get a closer view of some historic estates. A heaven for morning walkers, the sunsets at the lake must not be missed at any cost. The city has various golf courses too and offers finest restaurants to dine at. Thriving with life, the city does get a bit crowded during summers but is pretty relaxed during the fall.

Distance from Chicago: 1 hr 28 min (83.0 mi) via I-94 W and WI-50 W

Starved Rock State Park is located on the Illinois River and Fox River intersection, less than 100 miles from Chicago, . It boasts of over 13 miles of trails and is a paradise for hikers and adventure enthusiasts. Breathing in the lap of nature with waterfalls all around, Starved Rock State Park’s glacier-carved canyons and proximity to the Chicago city has made it a hot cake with visitors and camping lovers. Then there is fishing (ice fishing, too) and boating at the offer in the Illinois River. One can also opt for lodging overnight at the Starved Rock Lodge and enjoy various indoor activities like massage and live music performances. They also have river cruises, trolley tours, and guided hikes which one can opt for.
Distance from Chicago: 1 hr 48 min (98.9 mi) via I-80 W

The art coast of Michigan’, Saugatuck is not just any other beach city. It is known for its art galleries and various art fairs and exhibitions at the display. Attracting art lovers from around the globe, the city also houses one of the world’s most pristine beaches, the Oval Beach that offers kayaking, cruise on sailboats, and fishing to the visitors. Saugatuck is also known for its inclusive culture and open-minded lifestyle which celebrated the LGBTQ+ community. The city is gushing with life in the summers; however, it is equally pleasing during the fall.
Distance from Chicago: 2 hr 20 min (140.7 mi) via I-94 E and I-196 N

In the pristine surroundings of Sheboygan County, Wisconsin, lies the calm Elkhart Lake. Often overlooked by visitors, this laid-back destination boasts of pretty clear waters with fishing, kayaking, and paddleboarding opportunities. Elkhart Lake is also known for the famous racetrack. About 150 miles from Chicago, this place has many biking and hiking options, including the 1,200-mile Ice Age National Scenic Trail. Then there is Fireman's Park and Swimming Beach which is open for the public and is a great place to unwind with family and friends. One can even stay over at the beautiful lakeside resorts and cherish the local food and wine.

Distance from Chicago: 2 hr 42 min (150.5 mi) via I-94 W

Home to Ulysses S. Grant, Galena has over 1,000 buildings constructed before the 1900s. A dream town for any history lover, the 581-acre Galena Historic District is listed on the National Register of Historic Places. The town also has many art galleries and museums to spend quality time at. Galena is not only a town with a rich history, but also offers outdoor activities like rafting trips along the Mississippi River and hiking trails. The town has plenty of restaurants, pubs, and bars to enjoy nightlife as well, like the Galena Brewing Company, Nora Bar, and more.

Distance from Chicago: 3 hr 3 min (163.7 mi) via I-90 W and US-20 W/US Hwy 20 W

Madison is the capital of Wisconsin and is about 150 miles from Chicago. If one is looking for a fun getaway that celebrates mankind then this is the place to be. This state capital is full of students, professors, businessmen, politicians, and whatnot. Known for the beer and cheese, Madison is home to eight National Historic Landmarks, including one UNESCO World Heritage Site. Having said that, it does not make it only a historical city. Rather, it is known for its culinary scene. Enjoying live music while exploring local breweries is a dream that lies just about three hours’ drive from Chicago.
Distance from Chicago: 2 hr 17 min (147.3 mi) via I-90 W

Indianapolis or Indy, the state capital of Indiana is a must-visit place for anyone who wishes to experience life in full swing. Name it and the city has it. Indianapolis is also popular as the Racing Capital of the world and why not, the celebrations and festivals are in full swing all around the year. Also known for its museums, what attracts most people to Indy is its food scene. The City Market has many locally-owned eateries that serve as the gastronomical powerhouses. It is located about 185 miles from Chicago and serves as a brilliant getaway for those who want a break from routine and yet want to go out and have fun.
Distance from Chicago: 3 hr 1 min (185.4 mi) via I-65 S

Tired from the hustle of the city life and do not have much time in hand for an escape? South Haven, Michigan is the answer to that. This serene port city is a beauty to rejoice and unwind at. About two hours drive from Chicago, South Haven has various eateries where one can eat and enjoy the life in slow motion. The highlight, however, has to be the famous lighthouse that overlooks the Black River and has serves for over a century. The sandy and tranquil beach is the place to spend some time with family and friends, all the while taking in a spike of thrill with the water sports available.
Distance from Chicago: 1 hr 59 min (123.4 mi) via I-90 E and I-94 E

If a luxurious break with gourmet food is the mood of the hour, then Milwaukee in Wisconsin is the stop to be at. Located less than 100 miles north of Chicago, the city is known for its rich historical and cultural attractions. The city housed many German immigrants and hence one can witness the rich brewing tradition that began with them. The city has over 15 brewery tours making it difficult for one to not be spoilt for it. Then there is the Harley-Davidson Museum, Haggerty Museum of Art, and the Black Cat Alley which features the works of local artists. What’s more, bring a kayak or take one here, and vibe with the city while paddling in the Milwaukee River.
Distance from Chicago: 1 hr 28 min (93.1 mi) via I-94 W

An unconventional choice for a vacation, New Glarus, Wisconsin is located in Green County, Wisconsin. A small village, the place is known for its breweries and Swiss heritage. The old-world architecture is visible throughout the village and a small tour can take one to another time frame. Away from the crowds, New Glarus is indeed an escape in true sense. The New Glarus Brewing Company offers samples of custom beers and one can chill while getting lost in the rustic surroundings. There also are family restaurants where one can relax with kids and celebrate with Santa in the month of December.
Distance from Chicago: 2 hr 29 min (145.3 mi) via I-90 W

Situated in Cook County and barely nine miles from Downtown Chicago is the friendly neighbourhood of Oak Park, Illinois. Its proximity to the city makes it a hotspot for the last-minute getaway destinations from Chicago. It is a fun place to be with family and friends as it boasts of active art and culture scene. Home to various artists, Oak Park’s history comprises of Frank Lloyd Wright's Historic Home & Studio, Oak Park-River Forest Museum, and even the Birthplace of Ernest Hemingway. The cherry on top are the fun outdoor activities like rope bridges, zip lines at Go Ape Zipline Tree Top Adventure Course, and even spending time in the wild and bird watching.
Distance from Chicago: 12 min (9.1 mi) via I-290 W

Located about two hours drive from downtown Chicago, South Bend is a city in Indiana that is home to the famous University of Notre Dame. The city is a very interesting choice to visit for any historical or automobile enthusiast. The Studebaker National Museum is a mandatory visit for an autophile where the classic cars are at display. Visiting the scenic campus of Notre Dame or watching the Fighting Irish in person are dreams for any Irish fan that are fulfilled here. And then, contrary to this classic ambience, one can hit the rapids on North America’s first artificial white-water course, the East Race Waterway, which cuts through the city.
Distance from Chicago: 1 hr 41 min (95.7 mi) via I-90 E

Indiana Dunes is a United States National Park that is located about 45 miles from Chicago. Covering about 15 miles of Lake Michigan’s southern shore, this park is managed by National Park Service. Visitors have a plethora of activities to do which make it a brilliant and quick drive from Chicago for families and friends. Spread across 15,000 acres, Indiana Dunes offers 50 miles of trails for hikers, bird watching opportunities, kite flying on the sunny beach, or simply a walk in the mysterious and serene park. One can also witness the Chicago skyline from the beach and is definitely a sight to witness and introspect on the day away from the city hustle.
Distance from Chicago: 55 min (48.4 mi) via I-90 E

Holland is located on the shore of Lake Macatawa, just 150 miles from Chicago. It is a city bringing together the charm of a small-town and the facilities of a big city. The city boasts of white-sandy beaches, beautiful sunsets, and the famous Big Red Lighthouse. The downtown area of Holland is one of the world’s best Christmas markets and is a brilliant place to collect souvenirs and gifts.
The highlight of Holland has to be the Tulip Time Festival that celebrates the Dutch roots of the city and is a sight to behold with tulips blooming all around. Holland offers a perfect blend for vacationing after a busy week.
Distance from Chicago: 2 hr 27 min (150.9 mi) via I-94 E and I-196 N

To unwind the monotony of the week and release the pent-up tiredness, one has to make a stop at the Delavan Lake. Located in Walworth County, Wisconsin, Delavan Lake is full of recreational activities. Visitors can access the lake from the beach. Although the lake has murky waters, it boasts of fishes like the Musky, Panfish, Largemouth Bass, Smallmouth Bass, and Walleye, making it a nice fishing spot with friends and even kids. Delavan Lake has a depth of 52 feet and the most favourable time for fishing in the lake are early summer mornings or evenings. However, swimming is not allowed in the lake.
Distance from Chicago: 1 hr 38 min (88.4 mi) via I-90 W

Warren Dunes is a state park located along the Lake Michigan and spread across 1,952 acres. The park consists of a beautiful three-mile-long beach where one can swim, relax, and have a picnic with their families. What makes this park stand apart from others are the large sand dunes that are spread all over the park. The highest one being Tower Hill which is a fun place to scrambling up and sliding down its slopes. Another noteworthy activity in the park is metal hunting which is permitted in designated areas. It also has six miles of hiking trail and what’s more, it is a pet-friendly beach.
Distance from Chicago: 1 hr 28 min (82.8 mi) via I-90 E and I-94 E

Located just 70 miles from Chicago, New Buffalo is a beach town in Michigan. The main attraction of the town is the large beach, New Buffalo MI Beach, that provides an ideal family outing location. There are two waterfront hotels which can be reserved for a pristine view and a quality time. New Buffalo is a nice place to explore the nearby village along the lakeshore, breweries, and wineries. There are several cafés in the town itself and various antique shops for collectables. To add to it all, the town has many beautiful parks that serve as a nice picnic spot with kids.
Distance from Chicago: 1 hr 12 min (70.4 mi) via I-90 E and I-94 E