The Ultimate Guide to Road Trips from Chicago


Are you ready for an adventure? There’s nothing quite like a road trip to awaken your sense of exploration and freedom. And if you’re in Chicago, you’re in luck! The Windy City is the perfect starting point for some incredible road trips that will take you to breathtaking destinations and create lasting memories.

In this comprehensive guide, we will explore the best road trips from Chicago, highlighting the most scenic routes, iconic attractions, and hidden gems. Whether you’re looking for a day trip or a weekend getaway, we have you covered. So buckle up, roll down the windows, and let’s hit the road!

Road Trip Ideas from Chicago

1. Milwaukee: Discover the Charm of the Brew City

Just a short drive north from Chicago, Milwaukee is a vibrant city known for its rich brewing history, stunning architecture, and buzzing arts scene. Start your day trip by exploring the Milwaukee Art Museum, home to a diverse collection of over 30,000 artworks. Then, take a stroll along the picturesque Riverwalk and visit the historic Third Ward, filled with art galleries, boutiques, and restaurants. Don’t forget to indulge in some local craft beer at one of the city’s many breweries before heading back to Chicago.

2. Lake Geneva: A Scenic Retreat

Escape the hustle and bustle of the city with a road trip to Lake Geneva. Located just 80 miles northwest of Chicago, this picturesque resort town offers stunning views of the lake and a charming downtown area filled with boutique shops and cozy cafes. Spend the day exploring the lake by boat or kayak, or take a leisurely walk along the scenic Shore Path. Make sure to visit the historic Black Point Estate, a stunning mansion that offers a glimpse into the area’s rich history.

3. Saugatuck: A Quaint Coastal Getaway

If you’re craving a beachside retreat, Saugatuck is the perfect destination. Situated on the shores of Lake Michigan, this charming town is known for its sandy beaches, dune rides, and vibrant arts community. Spend the day lounging by the water, exploring the unique art galleries and boutiques in the downtown area, or taking a scenic hike through the Saugatuck Dunes State Park. Don’t forget to catch a breathtaking sunset over the lake before heading back to Chicago.

4. Starved Rock State Park: Nature’s Playground

For nature lovers, a trip to Starved Rock State Park is a must. Located just 90 miles southwest of Chicago, this stunning park offers scenic trails, waterfalls, and breathtaking views of the Illinois River. Spend the day hiking through the park’s 13 miles of trails, stop by the visitor center to learn about the area’s rich history, and enjoy a picnic surrounded by nature. If you’re feeling adventurous, you can even try your hand at rock climbing. Just remember to bring your camera to capture the beauty of this natural wonderland.

5. Galena: Step Back in Time

Travel back in time with a visit to Galena, a historic town nestled in the rolling hills of northwest Illinois. Known for its beautifully preserved 19th-century architecture, Galena offers a glimpse into the past. Take a stroll down Main Street, lined with charming shops and art galleries, and visit the Ulysses S. Grant Home, the former residence of the Civil War General and 18th President of the United States. For wine enthusiasts, a visit to one of the local wineries is a must. Unwind with a glass of locally produced wine while enjoying the scenic views of the countryside.

10 Awesome Road Trips from Chicago That Will Make Your Adventure Unforgettable

Frequently Asked Questions

1. How far is Milwaukee from Chicago?

Milwaukee is approximately 92 miles north of Chicago, making it a convenient and easily accessible day trip destination. The drive usually takes around 1.5 to 2 hours, depending on traffic conditions.

2. What is there to do in Lake Geneva?

Lake Geneva offers a wide range of activities for visitors of all ages. From relaxing boat rides to thrilling water sports, there’s something for everyone. You can explore the lake by renting a boat or kayak, visit the historic Black Point Estate, take a scenic hike, or simply relax on the sandy beaches.

3. Are there any hiking trails in Starved Rock State Park?

Yes, Starved Rock State Park is a hiker’s paradise. The park features 13 miles of scenic trails that wind through canyons, waterfalls, and lush forests. Whether you’re a beginner or an experienced hiker, you’ll find a trail that suits your skill level.

4. How long does it take to drive to Saugatuck from Chicago?

The drive from Chicago to Saugatuck usually takes around 2.5 to 3 hours,depending on traffic conditions. It’s a scenic route that takes you along the shores of Lake Michigan, offering beautiful views along the way.

5. What is the best time to visit Galena?

Galena is beautiful year-round, but each season offers a unique experience. The town is especially charming during the fall when the foliage is at its peak and during the winter when you can enjoy festive activities like ice skating and holiday shopping. Spring and summer are also great times to visit, with pleasant weather and outdoor events.


With so many incredible road trip options from Chicago, the possibilities for adventure are endless. Whether you’re seeking vibrant city vibes, scenic retreats, beachside getaways, or a step back in time, there’s a destination that will fulfill your desires. So pack your bags, fuel up your car, and embark on a road trip that will create memories to last a lifetime. Happy travels!

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