BEST ROAD TRIPS FROM CHICAGO: 10 Epic Journeys to Embark On

Chicago is a great city to start a road trip from. With its central location in the United States, there are many different directions you can go and many different types of scenery you can see.

In this blog post, we’ll share 10 epic road trips from Chicago, each with its own unique attractions. Whether you’re looking for a scenic drive, a cultural experience, or an outdoor adventure, there’s a road trip on this list for you.

Road Trips From Chicago

Chicago is a great starting point for road trips, offering a variety of destinations within a few hours’ drive. Whether you’re looking for a day trip, a weekend getaway, or a longer adventure, there are plenty of options to explore.

Types of Road Trips From Chicago

There are various types of road trips from Chicago, ranging in duration and distance. Some options include:

#1. Day Trips

If you’re looking for a quick getaway or want to explore nearby destinations, day trips are a great option. You can visit places like South Bend, Indiana, which is just an hour and 35 minutes away from Chicago. Other day trip options include Elgin, Illinois, known as the City in the Suburbs.

#2. Weekend Getaways (2-4 Days)

For a weekend getaway, consider visiting St. Louis, Missouri, and Cincinnati, Ohio, both within a 4- to 4.75-hour drive from Chicago, each with its own unique attractions to explore.

#3. Longer Road Trips (7–10 Days)

For those who want to embark on a more extended adventure, longer road trips are a great option. Consider destinations like Door County, Wisconsin, known for its coastal towns and outdoor activities, or Saugatuck, Michigan, famous for its dune rides and art galleries.

#4. Luxury Road Trips

For a luxurious road trip, consider luxury resorts, wineries, or scenic coastal drives. For instance, a Lake Michigan shoreline trip can involve exploring upscale beach towns and gourmet dining experiences, offering a more upscale and luxurious experience.

#5. Themed Road Trips

A themed road trip can be a unique way to explore different destinations and experiences, such as a foodie road trip where you try local specialties or a road trip focused on outdoor activities like hiking or camping. This allows you to customize your journey to your specific interests and passions.

#6. Historical Road Trips

A history enthusiast can embark on a road trip to visit significant historical sites and landmarks, such as Route 66, which starts in Chicago and extends to California. Along the way, they can visit iconic attractions, towns, and museums.

#7. Scenic Road Trips

Sightseeing road trips offer breathtaking landscapes and natural beauty, allowing visitors to explore picturesque national parks, scenic byways, or coastal drives. Popular destinations include the Great Smoky Mountains, the Door County Peninsula, and the Upper Peninsula of Michigan.

#8. Fall Foliage Road Trips

During the autumn season, you can plan a road trip to witness the vibrant colors of fall foliage. Explore destinations like Michigan’s Upper Peninsula, Wisconsin’s Door County, or the Shawnee National Forest in southern Illinois, where you can enjoy scenic drives surrounded by beautiful autumn colors.

#9. Coastal Road Trips

If you’re a fan of coastal scenery, you can plan a road trip along the shores of Lake Michigan. Explore charming beach towns like Saugatuck, Michigan, or drive along the Indiana Dunes National Park. These road trips offer stunning lake views, sandy beaches, and opportunities for water activities.

#10. National Park Road Trips

For nature enthusiasts, consider planning a road trip to nearby national parks like Cuyahoga Valley National Park in Ohio, Mammoth Cave National Park in Kentucky, or Voyageurs National Park in Minnesota, offering hiking, wildlife spotting, and nature-inspired beauty experiences.

Best Road Trips From Chicago

The best road trips from Chicago offer diverse experiences, including city exploration, nature immersion, and scenic drives. It’s crucial to plan your itinerary, check for travel restrictions, and enjoy the adventure!

The best road trips you can take from Chicago are:

#1. St. Louis, Missouri

St. Louis offers attractions like Forest Park, the Saint Louis Art Museum, the Saint Louis Science Center, and the Saint Louis Zoo. It’s a great destination for a family road trip.

#2. Cincinnati, Ohio

Cincinnati is a fantastic family-friendly destination with attractions such as the Cincinnati Zoo, the Cincinnati Museum Center, and the Newport Aquarium.

#3. Indiana Dunes, Indiana

Located just an hour away from downtown Chicago, Indiana Dunes National Park offers beautiful beaches, hiking trails, and stunning dunes.

#4. Saugatuck, Michigan

Saugatuck is a popular destination known for its dune rides, beaches, art galleries, and great restaurants. It’s about a 3-hour drive from Chicago and offers a variety of activities for both families and couples.

#5. Door County, Wisconsin

Door County is a picturesque destination known for its charming coastal towns, beautiful beaches, and outdoor activities. It’s approximately a 3-hour and 50-minute drive from Chicago.

#6. Lake Geneva, Wisconsin

Lake Geneva is a popular lake town with activities such as boat tours, water sports, golfing, and a water park. It’s about a 90-minute drive from Chicago.

#7. Michigan’s Upper Peninsula

The Upper Peninsula of Michigan offers stunning natural beauty, including waterfalls, forests, and the iconic Pictured Rocks National Lakeshore. It’s a longer road trip from Chicago but worth the journey.

#8. Route 66

Embark on a historic road trip along Route 66, starting from Chicago and heading west. This iconic route takes you through charming small towns, roadside attractions, and historic landmarks.

#9. Great Smoky Mountains National Park

Take a scenic drive from Chicago to the Great Smoky Mountains National Park, located on the border of Tennessee and North Carolina. Enjoy hiking, wildlife spotting, and breathtaking views of the mountains.

#10. Amish Country, Ohio

Explore the picturesque Amish Country in Ohio, known for its scenic countryside, Amish culture, and delicious homemade food. It’s a unique and peaceful road trip destination.

Family Road Trips From Chicago

Family road trips from Chicago destinations included St. Louis, Missouri, with attractions like Forest Park and the Saint Louis Zoo; Cincinnati, Ohio, known for the Cincinnati Zoo and the Cincinnati Museum Center; Lake Geneva, Wisconsin, offering activities such as boat tours and water parks; Saugatuck, Michigan, with dune rides and art galleries; Indiana Dunes, Indiana, featuring beautiful beaches and hiking trails. These road trips cater to families and provide a range of activities suitable for all ages.

Benefits of Family Road Trips From Chicago

Family road trips from Chicago offer several benefits for both parents and children. These benefits include

#1. Quality Time

Road trips provide an opportunity for families to spend quality time together, away from the distractions of daily life. It allows for bonding, shared experiences, and creating lasting memories.

#2. Exploration and Adventure

Road trips offer the chance to explore new destinations, whether it’s visiting national parks, charming towns, or iconic landmarks. It allows families to embark on exciting adventures and discover new places together.

#3. Flexibility and Freedom

Road trips provide the flexibility to create your itinerary and make spontaneous stops along the way. Families can adjust their plans based on their interests, allowing for a more personalized and enjoyable experience.

#4. Educational Opportunities

Road trips offer educational opportunities for children. They can learn about history, geography, and different cultures by visiting museums, historical sites, and landmarks along the route.

#5. Exposure to Different Cultures

Road trips allow families to experience different cultures and traditions firsthand. Exploring diverse destinations along the way exposes children to new languages, cuisines, and customs, fostering cultural awareness and appreciation.

#6. Outdoor Recreation

Road trips often involve visits to national parks, beaches, and other outdoor destinations. This provides families with opportunities for outdoor recreation such as hiking, swimming, fishing, and camping. It promotes physical activity and an appreciation for nature.

#7. Learning Opportunities

Road trips offer countless learning opportunities for children. They can learn about geography, history, and natural sciences through interactive experiences at museums, historical sites, and interpretive centers.

#8. Screen-Free Time

Having a road trip from Chicago provides an opportunity to disconnect from screens and technology. Instead of focusing on electronic devices, families can engage in face-to-face interactions, play games, or enjoy audiobooks and music together.

#9. Cultivating Independence

Family road trips can help children develop a sense of independence and responsibility. They can participate in planning the route, navigating, and contributing to decision-making, enhancing their self-confidence and decision-making abilities.

#10. Family Bonding

Spending extended time together in a car fosters family bonding. It allows for conversations, storytelling, and shared experiences that strengthen relationships and create a sense of togetherness.

Short Road Trips From Chicago

These short road trips provide a variety of experiences, from exploring cities and museums to enjoying outdoor adventures and natural beauty. Each destination offers unique attractions and experiences, making them suitable for day trips or quick getaways.

Here are some short road trips from Chicago:

#1. South Bend, Indiana

Located just 95 miles away from Chicago, South Bend offers attractions such as the University of Notre Dame, the Studebaker National Museum, and the Potawatomi Zoo. It’s a great destination for a day trip.

#2. Elgin, Illinois

Elgin is a city in the suburbs of Chicago, approximately an hour’s drive away. It features downtown Elgin with its public art, historic buildings, and the Elgin History Museum. It’s a convenient option for a day trip or a weekend getaway.

#3. Milwaukee, Wisconsin

Milwaukee is located about 90 miles north of Chicago, making it a convenient destination for a day trip. It offers attractions such as the Milwaukee Art Museum, the Harley-Davidson Museum, the Milwaukee Public Market, and the Milwaukee County Zoo.

#4. Starved Rock State Park, Illinois

Starved Rock State Park is located about 100 miles southwest of Chicago. It is known for its stunning canyons, waterfalls, and hiking trails, providing opportunities for outdoor activities and scenic views.

#5. Galena, Illinois

Galena is situated about a 3-hour drive northwest of Chicago. It is a historic town known for its well-preserved 19th-century buildings, boutique shops, art galleries, and scenic views of the Mississippi River.

#6. Wisconsin Dells, Wisconsin

Wisconsin Dells is located about 3 hours northwest of Chicago. It is a popular family-friendly destination with water parks, amusement parks, boat tours, and outdoor recreational activities.

#7. Iowa City, Iowa

About a 3-hour and 45-minute drive from Chicago, Iowa City is home to the University of Iowa and offers attractions like the Old Capitol Museum, the Iowa Children’s Museum, and the Devonian Fossil Gorge. It’s a great destination for a short road trip.

#8. Bloomington, Indiana

Bloomington is approximately a 4-hour drive from Chicago. It is home to Indiana University and offers attractions such as the WonderLab Museum of Science, Health, and Technology, Monroe Lake, and the Tibetan Mongolian Buddhist Cultural Center.

#9. New Buffalo, Michigan

New Buffalo is a charming beach town situated on the shores of Lake Michigan, only about an hour and a half drive from Chicago. It offers pristine beaches, waterfront dining, boutique shops, and the Four Winds Casino Resort.

#10. Madison, Wisconsin

About a two-hour drive northwest of Chicago, Madison is the capital of Wisconsin and offers a mix of natural beauty and cultural attractions. Visit the stunning Olbrich Botanical Gardens, explore the Wisconsin State Capitol, and enjoy the vibrant food and arts scene in the downtown area.

Road Trips From Chicago Couples

Road trips from Chicago that are ideal for couples destinations provide an opportunity for couples to relax, explore new places, and create romantic memories. These destinations include Lake Geneva, Wisconsin; Saugatuck, Michigan; Door County, Wisconsin; Indianapolis, Indiana; and Galena, Illinois. These locations offer various activities such as boat tours, beach walks, exploring charming towns, visiting museums, and enjoying local cuisine.

Tips For Road Trips From Chicago Couples

These are some tips for road trips from Chicago for couples:

#1. Plan Together

Sit down with your partner and plan the road trip together. Discuss the destinations, activities, and accommodations that interest both of you. This ensures that both partners have a say in the itinerary and creates a sense of shared excitement.

#2. Choose Romantic Destinations

Select destinations that offer a romantic atmosphere and activities. Look for places with scenic views, charming towns, and opportunities for intimate experiences such as beach walks, sunset cruises, or wine tastings.

#3. Pack Essentials

Make sure to pack essentials for the road trip, including comfortable clothing, toiletries, snacks, and entertainment for the journey. Don’t forget to bring items that can enhance the romantic atmosphere, such as candles, a picnic blanket, or a Bluetooth speaker for romantic music.

#4. Plan Romantic Activities

Research and plan activities that cater to your interests as a couple. This could include visiting art galleries, exploring botanical gardens, going on scenic hikes, or enjoying a couples’ spa day. Consider activities that allow you to connect and create lasting memories together.

#5. Take Scenic Routes

Opt for scenic routes instead of highways whenever possible. This allows you to enjoy beautiful landscapes and create a more memorable and romantic journey. Research scenic drives or detours along the way to make the road trip more enjoyable.

#6. Create a Romantic Playlist

Prepare a playlist of your favorite romantic songs or create a collaborative playlist with your partner. This will set the mood and enhance the romantic atmosphere during the road trip.

#7. Enjoy Quality Time

Use the road trip as an opportunity to disconnect from daily distractions and focus on quality time together. Engage in meaningful conversations, play road trip games, listen to music, or enjoy audiobooks together. Use this time to strengthen your bond and create shared experiences.

#8. Capture Memories

Bring a camera or use your smartphone to capture the special moments during the road trip. Take photos of scenic views, landmarks, and each other to create a visual record of your journey. These photos will serve as cherished memories of your time together.

#9. Plan Surprise Stops

Surprise your partner with unexpected stops along the way. Research hidden gems, scenic viewpoints, or charming roadside attractions that you can visit together. These surprises add an element of excitement and adventure to the trip.

#10. Surprise your Partner with Love Notes

Leave small love notes or surprise messages for your partner to find during the road trip. Hide them in the glove compartment, slip them into their bag, or leave them under the pillow in your hotel room. These little gestures can make the trip feel extra special.

What Is Drivable From Chicago?

Drivable destinations from Chicago include St. Louis, Missouri; South Bend, Indiana; Milwaukee, Wisconsin; Madison, Wisconsin; Door County, Wisconsin; and Iowa City, Iowa. These destinations offer a range of attractions, such as cultural sites, outdoor activities, scenic landscapes, and vibrant city experiences. They are all within a reasonable driving distance from Chicago, making them suitable options for day trips or weekend getaways.

What City Is 4 Hours Away From Chicago?

Cities that are approximately 4 hours away from Chicago are St. Louis, Missouri; Indianapolis, Indiana; Milwaukee, Wisconsin; Grand Rapids, Michigan; and Louisville, Kentucky. Each city offers its own unique attractions, such as iconic landmarks, cultural experiences, and outdoor activities.

What Cities Are 5 Hours From Chicago?

The cities that are approximately 5 hours away from Chicago include Traverse City, Michigan; Fort Wayne, Indiana; Galena, Illinois; Hendricks County, Indiana; and St. Louis, Missouri. Each city offers its own unique attractions, ranging from scenic landscapes to cultural experiences. Consider travel times and any potential travel restrictions before planning a road trip to these destinations.

What City Is 2 Hours Close To Chicago?

The cities that are 2 hours away from Chicago are Milwaukee, Wisconsin; South Bend, Indiana; Rockford, Illinois; Kalamazoo, Michigan; and Joliet, Illinois.

How Far Apart Are Chicago and New York?

The distance between Chicago, Illinois, and New York City, New York, is approximately 712 miles (1146 kilometers). The driving distance between the two cities is about 788 miles (1269 kilometers). The flight time from Chicago to New York is approximately 2 hours and 1 minute.

What Is The Famous Route From Chicago To California?

The famous route from Chicago to California is historic Route 66. Route 66 is a historic highway in the United States that runs southwestwardly from Chicago, Illinois, to Santa Monica, California, crossing eight states and covering over 2,400 miles (3,900 km).

Conclusion

Chicago offers diverse road trips to different destinations. Plan your itinerary, check travel restrictions, and enjoy the adventure. These trips provide opportunities for bonding, adventure, and cultural exposure. Short road trips from Chicago offer a variety of experiences, from exploring cities and museums to outdoor adventures and natural beauty. To plan a romantic trip, plan together, choose romantic destinations, pack essentials, and plan activities that cater to your interests and create lasting memories.