If you live in or around Chicago, you’re lucky to be surrounded by a wide range of fascinating destinations that are just a road trip away. From charming small towns to vibrant cities, from natural wonders to cultural hotspots, the Midwest offers plenty of options for those who love to hit the open road and discover new places.
In this article, we’ll take a closer look at some of the best road trips from Chicago, and provide tips and ideas for planning your own adventure. Whether you’re looking for a weekend getaway or a longer excursion, whether you prefer the beach or the mountains, whether you’re traveling solo or with a group, there’s something for everyone.
So pack your bags, buckle up, and get ready for a journey that will take you through scenic landscapes, historic landmarks, and hidden gems that you won’t find in a guidebook. Road trips are a great way to create memories, bond with your travel companions, and experience the freedom of the open road. And with Chicago as your starting point, you’re in for a treat.
Plan Your Weekend Trip
Weekend road trips from Chicago offer a great opportunity to explore the many unique destinations that the Midwest has to offer. Whether you’re seeking outdoor adventure, cultural experiences, or simply a change of scenery, there are plenty of great places to visit within a few hours’ drive of the city. From charming small towns to big-city attractions, the options are endless.
For outdoor enthusiasts, there are plenty of options for hiking, camping, fishing, and other outdoor activities within a few hours of Chicago. From the rugged beauty of Starved Rock State Park in Illinois to the stunning vistas of the Apostle Islands National Lakeshore in Wisconsin, there are plenty of opportunities to get out and explore the natural beauty of the region.
Of course, not every weekend trip has to involve outdoor adventure or quirky roadside attractions. There are also plenty of charming small towns and big cities to explore, each with their own unique character and attractions.
The Advantages Of Road Trips For Travelers
Road trips are an incredible way to explore nearby destinations, and there are many reasons why they are a great option for travelers. One of the main benefits of a road trip is the freedom it provides. When traveling by car, you can set your own pace and create a customized itinerary that suits your preferences. You can also take detours and explore off-the-beaten-path destinations, which may not be easily accessible by other means of transportation.
Another advantage of road trips is the opportunity to immerse yourself in the local culture and scenery. Driving through a region or a city allows you to experience the sights, sounds, and smells of the area in a way that you wouldn’t be able to if you were traveling by plane or train. You can also stop and visit local attractions, sample regional cuisine, and meet locals, which can provide a deeper and more meaningful travel experience.
Road trips can also be more budget-friendly than other types of travel. By driving your own car, you can avoid the high costs of airfare, train tickets, or rental cars. Additionally, you have more control over your expenses and can save money on food and lodging by packing your own snacks and booking affordable accommodations along the way.
Finally, road trips can be a great bonding experience for friends and family. Spending hours in the car together can be a fun and memorable way to strengthen relationships and create shared memories. With the ability to choose your own activities and destinations, you can create a trip that caters to everyone’s interests and preferences.
Overall, road trips are a fantastic way to explore nearby destinations. They offer freedom, flexibility, immersion in local culture, budget-friendliness, and a chance to bond with your travel companions. If you’re looking for a unique and adventurous way to travel, a road trip is definitely worth considering.
10 Best Road Trips From Chicago
Whether you’re seeking a relaxing getaway or an action-packed adventure, there’s a weekend road trip from Chicago that’s sure to meet your needs. With so many great destinations to choose from, the hardest part will be deciding where to go first. Here are a few suggestions for popular road trip destinations that can be easily reached from Chicago:
Lake Geneva, Wisconsin
Lake Geneva, Wisconsin is a popular road trip destination from Chicago, located just 80 miles northwest of the city. The drive takes about 1.5 hours, making it an easy day trip or weekend getaway.
Lake Geneva is a resort town situated on the shores of a crystal-clear lake with stunning views of rolling hills and lush forests. The town is known for its historic mansions, scenic parks, and charming downtown area with unique boutiques, art galleries, and restaurants.
One of the main attractions in Lake Geneva is the lake itself, which offers a variety of water activities such as boating, kayaking, paddle boarding, and swimming. Visitors can also explore the miles of hiking and biking trails surrounding the lake, or take a leisurely stroll through the picturesque neighborhoods with stunning views of the water and gardens.
Lake Geneva is also home to many cultural attractions, such as the Geneva Lake Museum and the Horticultural Hall, which showcase the town’s rich history and artistic heritage. Additionally, visitors can indulge in local cuisine and wines, with many farm-to-table restaurants and vineyards located in the surrounding countryside.
Overall, Lake Geneva is a fantastic road trip destination from Chicago, offering a blend of natural beauty, outdoor recreation, cultural attractions, and delicious cuisine.
Another great road trip destination from Chicago is Saugatuck, Michigan, located on the shores of Lake Michigan, about 140 miles northeast of Chicago. The drive takes around 2.5 hours, making it a perfect weekend or extended getaway.
Saugatuck is known for its picturesque small-town charm, pristine beaches, and unique art scene. The town is surrounded by dunes and lush forests, providing plenty of opportunities for outdoor activities such as hiking, biking, and boating.
One of the main attractions in Saugatuck is Oval Beach, a stunning mile-long stretch of sand dunes and clear blue waters. Visitors can relax on the beach, swim, sunbathe, and take in the breathtaking views of Lake Michigan.
Saugatuck is also home to many art galleries, studios, and theaters, showcasing the work of local artists and performers. Visitors can explore the town’s vibrant art scene, attend live music and theater events, and participate in art workshops and classes.
In addition to its natural beauty and art scene, Saugatuck has a charming downtown area with unique shops, restaurants, and cafes. Visitors can stroll along the streets, sample local cuisine, and browse for one-of-a-kind souvenirs and gifts.
Overall, Saugatuck is a wonderful road trip destination from Chicago, offering a mix of natural beauty, outdoor activities, artistic experiences, and small-town charm.
Galena, Illinois is another fantastic road trip destination from Chicago, located in the northwest part of the state, about 160 miles west of the city. The drive takes around 3 hours, making it a perfect weekend getaway.
Galena is a charming small town with a rich history and stunning architecture. The town is known for its well-preserved 19th-century buildings and its association with former President Ulysses S. Grant, who lived in Galena after the Civil War.
One of the main attractions in Galena is the downtown area, which is lined with unique shops, restaurants, and galleries housed in historic buildings. Visitors can explore the town’s rich history by taking a walking tour or visiting museums, such as the Ulysses S. Grant Home State Historic Site.
Galena is also surrounded by beautiful natural scenery, with rolling hills, scenic overlooks, and hiking trails. Visitors can explore nearby state parks, such as the Apple River Canyon State Park, or take a scenic drive along the Mississippi River.
In addition to its historic charm and natural beauty, Galena is known for its culinary scene, with many restaurants offering farm-to-table cuisine and local wines. Visitors can sample the town’s unique flavors and experience its vibrant culinary culture.
Overall, Galena is a wonderful road trip destination from Chicago, offering a blend of history, natural beauty, culinary experiences, and small-town charm.
Indianapolis, Indiana is a fantastic road trip destination from Chicago, located in the heart of the state, about 180 miles southeast of the city. The drive takes around 3 hours, making it a perfect weekend or extended getaway.
Indianapolis is known for its world-class museums, beautiful parks, and vibrant downtown area. Visitors can explore the city’s rich cultural heritage by visiting museums such as the Indianapolis Museum of Art or the Children’s Museum of Indianapolis, one of the largest children’s museums in the world.
One of the main attractions in Indianapolis is the downtown area, which is home to the Indianapolis Motor Speedway, home of the famous Indy 500 race. Visitors can tour the speedway and museum, or attend a race or other events throughout the year.
Indianapolis is also surrounded by beautiful parks and outdoor spaces, such as the White River State Park or Eagle Creek Park. Visitors can enjoy hiking, biking, or kayaking, or simply relax and take in the natural beauty.
In addition to its cultural and outdoor attractions, Indianapolis has a vibrant culinary scene, with many restaurants offering farm-to-table cuisine and local beers. Visitors can sample the town’s unique flavors and experience its vibrant culinary culture.
Overall, Indianapolis is a wonderful road trip destination from Chicago, offering a blend of history, culture, outdoor activities, and culinary experiences.
Mackinac Island, Michigan
from Chicago. The island is famous for its idyllic Victorian architecture, horse-drawn carriages, and delicious fudge shops. Visitors can explore the island on foot, bike, or horseback, and take in stunning views of Lake Huron from vantage points like Arch Rock and the Grand Hotel’s porch.
One of the island’s unique features is its ban on cars – the only motorized vehicles allowed on the island are emergency vehicles and service vehicles. This makes for a peaceful and relaxing atmosphere that feels like a step back in time. Mackinac Island is a perfect weekend getaway for those looking to escape the hustle and bustle of city life and immerse themselves in the natural beauty and small-town charm of this historic island.
Shawnee National Forest
Shawnee National Forest is a vast expanse of protected wilderness located in southern Illinois, around a 6-hour drive from Chicago. The forest covers over 280,000 acres and offers visitors a variety of outdoor recreation opportunities, including hiking, camping, fishing, and hunting. The forest is known for its rugged landscapes, including towering sandstone bluffs, deep canyons, and cascading waterfalls. Visitors can explore miles of trails that wind through the forest, including the popular River to River Trail that spans the length of the forest.
Some of the most popular attractions in Shawnee National Forest include Garden of the Gods, a breathtaking rock formation that offers sweeping views of the surrounding landscape, and the 155-foot-tall Pomona Natural Bridge, one of the largest natural bridges in the world. With its diverse array of landscapes and outdoor activities, Shawnee National Forest is a must-visit destination for nature lovers and outdoor enthusiasts.
Milwaukee is a vibrant city located on the shores of Lake Michigan, just a 90-minute drive from Chicago. The city is known for its rich history, cultural attractions, and world-class breweries. Visitors can explore the Milwaukee Art Museum, which features a stunning collection of over 25,000 works of art from around the world, or take a tour of the Harley-Davidson Museum, which showcases the history of this iconic American motorcycle company. Beer lovers won’t want to miss a visit to the Miller Brewery, where they can take a tour and learn about the beer-making process.
Other popular attractions in Milwaukee include the historic Third Ward neighborhood, which is home to many galleries, shops, and restaurants, and the beautiful Lakefront Trail, which offers stunning views of Lake Michigan and the city skyline. With its unique blend of culture, history, and natural beauty, Milwaukee is a fantastic destination for a day trip or a weekend getaway from Chicago.
Michigan Maritime Museum
The Michigan Maritime Museum is a fascinating destination located in South Haven, Michigan, around a 2.5-hour drive from Chicago. The museum is dedicated to preserving and sharing the maritime history of the Great Lakes region, and features a collection of historic vessels, artifacts, and exhibits that offer insight into the area’s rich maritime heritage.
Visitors can explore the museum’s exhibits, which include a working replica of a 19th-century Great Lakes schooner, a restored 1920s commercial fishing boat, and an exhibit on the Michigan lighthouse system. The museum also offers a variety of educational programs and events throughout the year, including sailing lessons, boat-building workshops, and live music performances. South Haven itself is a charming lakefront town with plenty of shops, restaurants, and attractions to explore, making the Michigan Maritime Museum a great destination for a day trip or weekend getaway from Chicago.
The Chicago Botanic Garden is a world-renowned destination for plant lovers and garden enthusiasts, located around a 30-minute drive north of downtown Chicago. The garden covers over 385 acres and features 27 display gardens and four natural areas, including a Japanese garden, a rose garden, a sensory garden, and a prairie garden. Visitors can take a leisurely stroll through the gardens, attend one of the many educational programs or events offered throughout the year, or explore the many walking and hiking trails that wind through the natural areas.
The garden also offers a variety of dining options, including a cafe and a fine-dining restaurant. With its stunning array of plants and flowers, tranquil water features, and breathtaking landscapes, the Chicago Botanic Garden is a must-visit destination for nature lovers and anyone seeking a peaceful escape from the city.
New Buffalo is a charming lakefront town located just across the border from Michigan, around a 1.5-hour drive from Chicago. The town is known for its beautiful beaches, quaint shops, and excellent dining options. Visitors can spend the day lounging on the sandy shores of Lake Michigan or explore the nearby Galien River Marsh Preserve, which offers opportunities for hiking, birdwatching, and kayaking.
New Buffalo’s downtown area is home to a variety of shops and boutiques, selling everything from artisanal cheeses to locally-made pottery. The town is also known for its excellent dining options, with several restaurants offering farm-to-table cuisine, fresh seafood, and other delicious options. With its laid-back vibe, beautiful scenery, and easy access from Chicago, New Buffalo is a great destination for a day trip or weekend getaway.
In conclusion, the Midwest offers a wealth of exciting and unique destinations that are just a short drive away from Chicago. Whether you’re seeking outdoor adventure, cultural experiences, or just a change of scenery, there are plenty of great options for weekend road trips from the city. From charming small towns to big-city attractions, quirky roadside stops to natural wonders, there’s something for everyone within a few hours’ drive of Chicago. So pack your bags, hit the road, and explore all that the Midwest has to offer on your next weekend getaway.