Key Highlights
- Explore the natural beauty of Starved Rock State Park and enjoy hiking and waterfalls
- Visit the stunning Indiana Dunes National Park and spend a day on the sandy beaches
- Discover the charming town of Galena, Illinois with its rolling hills and historic charm
- Relax in the resort town of Saugatuck, Michigan and explore its art galleries and beautiful Oval Beach
- Experience the vibrant art scene in Milwaukee, Wisconsin and enjoy views of Lake Michigan
Introduction
Chicago, the Windy City, is a bustling metropolis filled with skyscrapers, world-class museums, and a vibrant culture. But sometimes, you need to escape the city and hit the open road for a memorable adventure. Luckily, Chicago is surrounded by numerous road trip destinations that offer stunning natural beauty, charming towns, and unique attractions. Whether you’re looking for a day trip or a weekend getaway, there are plenty of options within a few hours’ drive of Chicago.
From the picturesque shores of Lake Michigan to the rolling hills of Illinois and the vibrant cities of Wisconsin and Michigan, there’s something for everyone in this list of ultimate road trips from Chicago. So pack your bags, fill up the tank, and get ready to embark on an unforgettable road trip adventure from the Windy City.
Ready For the Best Road Trips from Chicago?
Many exciting road trips from Chicago are under three hours away and explore diverse destinations rich with natural wonders and cultural experiences. Traverse to Starved Rock State Park in Illinois for majestic canyons and waterfalls, or head to Indiana Dunes National Park for sandy shorelines along Lake Michigan. Discover the charm of Lake Geneva in Wisconsin or the historic town of Galena in Illinois, each offering a unique escape. Experience the artsy vibes of Saugatuck in Michigan or the vibrant city of Milwaukee in Wisconsin. Nearby gems like Madison and Door County in Wisconsin promise scenic beauty and outdoor adventures, perfect for a quick getaway.
15 Top Road Trips from Chicago
Chicago is the perfect starting point for exciting road trips. Whether you’re looking for natural beauty, historical sites, or vibrant cities, there’s a road trip for everyone. From the stunning Starved Rock State Park in Illinois to the picturesque Door County in Wisconsin, there are endless options to explore. Take a drive to the charming town of Galena, Illinois, known for its rolling hills and historic charm. Or head north to Saugatuck, Michigan, a resort town with art galleries and a beautiful beach. Don’t forget to visit Milwaukee, Wisconsin, and discover its vibrant art scene and views of Lake Michigan. With so many options, the road trips from Chicago are sure to provide unforgettable experiences.
Make your reservation so you will not be locked out of any lodging. So many people enjoy road trips from Chicago!
1. Starved Rock State Park, Illinois
Located just a short drive from Chicago, Starved Rock State Park is a nature lover’s paradise. With its towering canyons, cascading waterfalls, and breathtaking views of the Illinois River, it’s no wonder this park is a popular destination for day trips. Hike the trails that wind through the park and take in the stunning vistas from the top of Starved Rock, a sandstone butte that rises 125 feet above the river. Don’t miss the park’s waterfalls, including the iconic LaSalle Canyon waterfall, which can be seen from a boardwalk trail.
With its abundant wildlife, scenic overlooks, and picnic areas, Starved Rock State Park is the perfect place to escape the hustle and bustle of the city and reconnect with nature.
2. Indiana Dunes National Park, Indiana
Just a short drive from Chicago, Indiana Dunes National Park offers a unique combination of sandy beaches, towering sand dunes, and diverse ecosystems. Explore the park’s 15,000 acres of preserved land, where you can hike through forests, paddle along the shoreline, and admire the stunning views of Lake Michigan. Don’t miss the opportunity to climb the 125-foot-tall Mount Baldy, one of the park’s most iconic sand dunes.
Or relax on the beautiful beaches and soak up the sun. With its diverse range of activities and natural beauty, Indiana Dunes National Park is a must-visit destination for nature lovers and outdoor enthusiasts.
3. Lake Geneva, Wisconsin
If you’re looking for a family-friendly road trip destination near Chicago, look no further than Lake Geneva, Wisconsin. This charming resort town offers a wide range of activities for all ages.
Spend the day at one of the area’s water parks, like Timber Ridge Lodge and Waterpark or the indoor water park at Grand Geneva Resort. If you’re looking for a family-friendly road trip destination near Chicago, look no further than Lake Geneva, Wisconsin. This charming resort town offers a wide range of activities for all ages. Spend the day at one of the area’s water parks, like Timber Ridge Lodge and Waterpark or the indoor water park at Grand Geneva Resort. Enjoy outdoor activities like boating, fishing, and hiking along the scenic lakeshore. Take a stroll through the town’s historic district, filled with unique shops and restaurants. And don’t forget to indulge in some delicious ice cream at one of the local ice cream parlors. With its beautiful lake views and endless outdoor adventures, Lake Geneva is the perfect destination for a fun-filled road trip.
4. Galena, Illinois
Escape the hustle and bustle of the city and take a road trip to Galena, Illinois. This charming small town is nestled among rolling hills and offers a glimpse into the past with its well-preserved 19th-century architecture. Take a stroll down Main Street and explore the town’s unique shops, art galleries, and antique stores.
Visit the Ulysses S. Grant Home State Historic Site and learn about the life and presidency of the Civil War general and 18th President of the United States.
The Great Galena Balloon Race is a do not miss adventure. Take a scenic drive along the Galena River and enjoy the stunning views of the surrounding countryside. With its historic charm and natural beauty, Galena is the perfect destination for a relaxing road trip.
5. Saugatuck, Michigan
For a road trip that combines art, nature, and a charming resort town, head to Saugatuck, Michigan. This picturesque town is known for its vibrant art scene, beautiful beaches, and quaint downtown area. Explore the many art galleries and studios, where you can find unique pieces of artwork created by local artists. Spend the day at Oval Beach, one of the most beautiful beaches in the Midwest, and soak up the sun or take a dip in Lake Michigan.
Take a stroll through the downtown area and browse the boutiques, shops, and restaurants. With its combination of art, nature, and small-town charm, Saugatuck is the perfect destination for a road trip getaway.
6. Milwaukee, Wisconsin
Just a short drive north of Chicago, Milwaukee offers a unique combination of art, culture, and scenic views of Lake Michigan. Start your visit with a trip to the Milwaukee Art Museum, known for its stunning architecture and impressive collection of artwork. Explore the city’s vibrant public art scene, with murals and sculptures scattered throughout the downtown area. Take a stroll along the lakefront and enjoy the panoramic views of Lake Michigan. Don’t miss the chance to visit the Harley-Davidson Museum and learn about the history and culture of this iconic American motorcycle brand. With its diverse range of attractions and beautiful lake views, Milwaukee is a road trip destination that is sure to captivate visitors of all ages.
7. Madison, Wisconsin
The capital city of Wisconsin, Madison, offers a blend of natural beauty, vibrant culture, and a thriving food scene. Start your visit with a trip to the beautiful Olbrich Botanical Gardens, where you can explore stunning gardens and enjoy the peaceful atmosphere. Take a stroll through the University of Wisconsin-Madison campus and admire the historic buildings and lush green spaces. Visit the Wisconsin State Capitol and take a guided tour to learn about the history and architecture of this iconic building.
Don’t miss the chance to explore the nearby Devil’s Lake State Park, a local favorite for hiking, swimming, and picnicking. With its combination of natural beauty and cultural attractions, Madison is a road trip destination that is sure to please.
8. Door County, Wisconsin
Located on a picturesque peninsula between Green Bay and Lake Michigan, Door County is a popular road trip destination known for its stunning natural beauty and outdoor activities. Explore the numerous state parks and nature preserves, where you can hike, bike, or kayak through pristine forests and along scenic shorelines. Take a scenic drive along the Door County Coastal Byway and enjoy the panoramic views of the lake and countryside.
Visit the charming towns of Fish Creek, Ephraim, and Sister Bay, where you can browse art galleries, shop for unique souvenirs, and indulge in delicious local cuisine. With its idyllic landscapes and charming small towns, Door County is the perfect destination for a relaxing and scenic road trip.
9. Holland, Michigan
For a road trip that combines Dutch heritage and beautiful flowers, head to Holland, Michigan. Known for its vibrant tulip fields and annual Tulip Time Festival, Holland is a must-visit destination for flower and culture lovers. Explore the stunning tulip gardens at Windmill Island Gardens, where you can admire thousands of colorful blooms and learn about Dutch culture and history.
Visit the DeZwaan Windmill, the only authentic Dutch windmill in the United States, and take a guided tour to learn about its history and operation. Don’t miss the chance to explore the charming downtown area, with its unique shops, restaurants, and art galleries. With its Dutch heritage and beautiful flowers, Holland is a road trip destination that is sure to delight visitors of all ages.
10. Springfield, Illinois
For history buffs, a road trip to Springfield, Illinois is a must. This capital city is known for its rich history and association with Abraham Lincoln, the 16th President of the United States. Visit the Abraham Lincoln Presidential Library and Museum, where you can learn about Lincoln’s life and legacy through exhibits and interactive displays. Explore the Lincoln Home National Historic Site, where you can tour the only home that Lincoln ever owned. Don’t miss the chance to visit the Old State Capitol, where Lincoln delivered his famous “House Divided” speech. With its historic sites and connection to Abraham Lincoln, Springfield is a road trip destination that offers a fascinating journey into the past.
11. Cedarburg, Wisconsin
Step back in time and visit the charming town of Cedarburg, Wisconsin. With its well-preserved historic buildings and small-town charm, Cedarburg offers a unique road trip experience. Take a stroll down Washington Avenue and admire the beautiful 19th-century architecture.
Browse the numerous shops, art galleries, and antique stores that line the streets. Don’t miss the chance to visit the Cedar Creek Settlement, a collection of historic buildings that now house shops, cafes, and art studios. Enjoy a meal at one of the town’s restaurants, many of which offer outdoor dining options. With its historic charm and small-town feel, Cedarburg is the perfect destination for a peaceful and nostalgic road trip.
12. Michigan City, Indiana
Located on the shores of Lake Michigan, Michigan City, Indiana offers a delightful beach getaway just a short drive from Chicago. Spend the day at the picturesque Washington Park Beach, where you can relax on the sandy shores and swim in the clear waters of Lake Michigan. Visit the historic Michigan City Lighthouse and take in the panoramic views of the lake and the city.
Located on the shores of Lake Michigan, Michigan City, Indiana offers a delightful beach getaway just a short drive from Chicago. Spend the day at the picturesque Washington Park Beach, where you can relax on the sandy shores and swim in the clear waters of Lake Michigan. Visit the historic Michigan City Lighthouse and take in the panoramic views of the lake and the city. Explore the nearby Indiana Dunes National Park and hike along the sandy trails or go birdwatching in the wetlands. Don’t miss the chance to visit the Blue Chip Casino and try your luck at the slot machines or enjoy a delicious meal at one of the many restaurants. With its beautiful beaches and leisurely atmosphere, Michigan City is the perfect destination for a relaxing and fun-filled road trip.
13. Elkhart Lake, Wisconsin
For a road trip destination that combines adrenaline-pumping road racing and lake fun, head to Elkhart Lake, Wisconsin. This small town is known for its historic road racing circuit, Road America, where you can watch thrilling races or even participate in a driving experience. Spend the day at the beautiful Elkhart Lake, where you can swim, kayak, or paddleboard on the crystal-clear waters. Enjoy a picnic on the lakefront or rent a boat and explore the lake at your own pace. Don’t miss the chance to visit the Osthoff Resort, a luxury resort located on the shores of Elkhart Lake, where you can relax in the spa or enjoy a delicious meal with lake views. With its unique combination of road racing and lake activities, Elkhart Lake is the perfect destination for a road trip that offers something for everyone.
14. Shawnee National Forest, Illinois
Escape to the natural wonders of Shawnee National Forest in southern Illinois. This vast forest offers a variety of outdoor activities and stunning natural beauty. Hike through the forest and marvel at the unique rock formations, including the iconic Garden of the Gods, where massive sandstone cliffs rise above the surrounding landscape. Explore the numerous trails that wind through the forest, leading to hidden waterfalls and breathtaking vistas.
Don’t miss the chance to visit the Shawnee Wine Trail, where you can sample local wines and enjoy the scenic views of the vineyards. With its natural wonders and outdoor adventures, Shawnee National Forest is the perfect destination for a road trip that immerses you in the beauty of nature.
15. Ottawa, Illinois
Located in southern Illinois, Ottawa is a charming town that offers a variety of attractions and outdoor activities. It is located close to the historic Starved Rock Lodge and the nearby Starved Rock State Park, known for its stunning canyons and waterfalls. Take a scenic drive along the Illinois River Road and enjoy the beautiful views of the river and surrounding countryside. Explore the quaint downtown area, with its unique shops, art galleries, and restaurants. Don’t miss the chance to visit the Illinois Waterway Visitor Center and learn about the history and importance of the Illinois Waterway. With its natural beauty and small-town charm, Ottawa is the perfect destination for a road trip that takes you off the beaten path and into the heart of southern Illinois.
Planning Your Road Trip from Chicago
Planning a road trip from Chicago requires some careful preparation to ensure a smooth and enjoyable journey. Here are some essential tips to keep in mind:
- Plan your route and make a list of must-visit destinations along the way
- Check the weather forecast and pack accordingly
- Make sure your vehicle is in good condition and fill up on gas before you hit the road
- Research accommodations and make reservations in advance
- Pack snacks, drinks, and entertainment for the drive
- Check for any road closures or construction updates before you leave
- Have a backup plan in case of unexpected detours or delays
Essential Tips for a Smooth Journey
- Research the best places to visit and plan your itinerary accordingly
- Pack light and bring only essential items
- Check the local weather forecast and pack appropriate clothing
- Make sure your vehicle is in good condition and has been serviced before the trip
- Take breaks and stretch your legs during long drives
- Bring a GPS or map to navigate unfamiliar routes
- Pack snacks, water, and entertainment to keep yourself and your passengers occupied during the drive
Best Times of the Year to Travel
The best time of year to take a road trip from Chicago depends on your preferences and the destinations you plan to visit. Summer is a popular time to travel, as the weather is warm and many attractions are open. This is especially true for destinations like Six Flags Great America and the Wisconsin Dells, known as the Waterpark Capital of the World. Spring and fall offer milder weather and fewer crowds, making them ideal for outdoor activities and exploring nature. Winter can be a great time to visit if you enjoy winter sports or holiday festivities. Consider the weather conditions, peak seasons, off-season discounts, and travel costs when planning your road trip from Chicago.
What to Pack for Your Road Trips from Chicago
Packing for a road trip from Chicago requires some careful planning to ensure you have everything you need for a comfortable and enjoyable journey. Here are some essentials to consider packing:
- Comfortable clothing and shoes for different weather conditions
- Toiletries and personal care items
- Snacks, drinks, and a cooler to keep them fresh
- Entertainment options such as books, games, and music
- Roadside emergency kit and first aid supplies
- Maps or a GPS device for navigation
- Chargers for electronic devices
- Extra blankets and pillows for comfort during rest stops
- Travel documents, including identification and insurance information
Road Trip Necessities
- Comfortable clothing and shoes for walking and outdoor activities
- Sunscreen and insect repellent for protection from the elements
- Water bottles to stay hydrated during the drive
- Snacks and a cooler to keep them fresh
- Cash and credit cards for expenses along the way
- Entertainment options such as books, games, and music
- A camera to capture the memories
- A road atlas or GPS device for navigation
- A first aid kit for any minor injuries or illnesses
- A portable phone charger for emergencies
Entertainment for the Drive
- Create a road trip playlist with your favorite songs and artists
- Download podcasts or audiobooks for a more immersive experience
- Play car games like “I Spy” or trivia to keep everyone engaged
- Bring along a portable DVD player or tablet for movies or TV shows
- Have a selection of books or magazines for reading during rest stops
- Pack a deck of cards or other portable games for some friendly competition
- Use apps like Spotify or Pandora to discover new music or podcasts
- Prepare a list of podcasts or educational audio programs to learn something new during the drive
- Take advantage of the scenery by playing “Road Trip Bingo” or other observation games
- Make a travel journal or scrapbook to document the trip
Staying Safe on the Road Trips from Chicago
Safety should always be a top priority. Here are some tips to ensure a safe and enjoyable journey when taking road trips from Chicago:
- Always wear your seatbelt and ensure all passengers are properly restrained
- Avoid distractions while driving, such as using your phone or eating
- Take regular breaks to rest and stretch your legs
- Keep a safe following distance from other vehicles
- Be prepared for emergencies with a roadside emergency kit and a first aid kit
- Stay alert and aware of your surroundings
- Follow the rules of the road and be respectful of other drivers
- Monitor weather conditions and adjust your driving accordingly
What to Do in Case of an Emergency
In case of an emergency during your road trip from Chicago, it’s important to be prepared and know what to do. Here are some steps to take in different emergency situations:
| Emergency | Steps to Take |
| Car breakdown | Pull over to a safe location, turn on hazard lights, and call for roadside assistance or a tow truck |
| Medical emergency | Call emergency services (911 in the United States), provide necessary first aid if trained, and seek medical help |
| Severe weather | Find a safe place to take shelter, such as a nearby building or rest area, and monitor weather updates |
| Accident | Check for injuries and call emergency services if necessary, exchange information with other parties involved, and document the accident |
| Lost or stolen belongings | Report the incident to the local authorities, contact your insurance provider if necessary, and take steps to replace lost or stolen items |
It’s always a good idea to have emergency numbers saved in your phone and carry a first aid kit in case of minor injuries.
Conclusion
Embark on unforgettable road trips from Chicago to discover hidden gems and natural wonders within a few hours’ drive. From the majestic Starved Rock State Park to the serene Lake Geneva, each destination promises unique experiences. Plan your journey with essential tips for a safe and enjoyable adventure, ensuring you’re well-prepared and informed. Whether you prefer a solo escapade or a budget-friendly group expedition, these road trips offer something for everyone. Pack your bags, hit the road, and create lasting memories on these ultimate routes from the bustling city of Chicago.
Frequently Asked Questions
What is the best time of year to take a road trip from Chicago?
The best time of year to take a road trip from Chicago depends on your preferences and the destinations you plan to visit. Summer offers warm weather and many attractions are open, while spring and fall offer milder weather and fewer crowds.
How do I plan my route for a road trip from Chicago?
To plan your route for a road trip from Chicago, use a GPS or online mapping tool to determine the best route. Consider scenic routes and plan for rest stops along the way to break up the drive.
Are there any hidden gems close to Chicago for road trippers?
Yes, there are several hidden gems close to Chicago for road trippers. Consider visiting lesser-known destinations like Cedarburg, Wisconsin, or Ottawa, Illinois, for a unique and off-the-beaten-path experience.
What should I pack for a road trip during winter?
For a road trip during winter, pack warm clothing, including hats, gloves, and boots. Prepare your vehicle by checking the battery, tire pressure, and fluid levels. Carry a snowbrush and ice scraper for clearing your windows.
How can I make my road trip from Chicago more enjoyable?
To make your road trip from Chicago more enjoyable, bring along entertainment like travel games or audiobooks, pack snacks and drinks, and create a music playlist with your favorite songs.
Can I complete a road trip from Chicago on a budget?
Yes, it is possible to complete a road trip from Chicago on a budget. Look for cost-saving tips like packing your own meals, staying in affordable accommodations, and choosing free or low-cost activities.
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