10 Best Day Trips from Chicago

Chicago is full of attractions but sometimes, you may want to escape the city for something a little different; we share the best day trips from Chicago, so you can do just that.

Why take a day trip from Chicago?

Road trips are always fun and memorable, especially if you are traveling with your family or close friends. Exploring new destinations and trying out exciting adventures are valuable experiences that you cannot put a price on.

Whether you’re planning to visit historical sites or want to immerse in cultural experiences, Chicago serves as an excellent starting point for a plethora of exciting day trips.

From vibrant cities and charming towns to stunning natural wonders, the surrounding region offers a diverse range of wonderful places you can drive to with the help of luxury car rentals Chicago service. While public transportation systems are available in Chicago, driving a private or rental car is the best way to experience day trips.

Best Destinations for Day Trips from Chicago

If you are ready to embark on an unforgettable journey, here are 10 best day trips from Chicago, perfect for all types of travelers.

1. Milwaukee, Wisconsin

Located just 90 miles north of Chicago, Milwaukee is known for its vibrant cultural scene, and historic sites like the Milwaukee Art Museum, Harley-Davidson Museum, and the Milwaukee Public Market. Enjoy the city’s breweries, and waterfront activities, and explore its rich history and diverse neighborhoods.

2. Starved Rock State Park, Illinois

Situated around 90 miles southwest of Chicago, Starved Rock State Park features stunning canyons, waterfalls, and hiking trails. It’s an excellent destination for nature lovers and outdoor enthusiasts, offering breathtaking views of the Illinois River and opportunities for hiking, picnicking, and wildlife spotting.

3. Galena, Illinois

Located about a three-hour drive northwest of Chicago, Galena is a charming little town known for its well-preserved historic architecture. Take a stroll through Main Street, visit President Ulysses S. Grant’s home, explore boutique shops and art galleries, and enjoy scenic views of the Mississippi River.

4. Indiana Dunes National Park, Indiana

Located approximately 50 miles southeast of Chicago, Indiana Dunes National Park offers beautiful sandy beaches, dunes, and diverse ecosystems. It’s a perfect destination for hiking, birdwatching, and relaxing by the lake. Explore trails, climb sand dunes, or take a swim in Lake Michigan.

5. Frank Lloyd Wright Home and Studio, Oak Park, Illinois

Just a short drive from downtown Chicago, Oak Park is where you can visit the former home and studio of renowned architect Frank Lloyd Wright. Explore his architectural masterpieces, including the Robie House and Unity Temple, and learn about his influential work that shaped modern architecture.

6. Lake Geneva, Wisconsin

Situated about 80 miles northwest of Chicago, Lake Geneva is a resort town known for its picturesque lake, beautiful mansions, and outdoor activities like boating, fishing, and hiking. Enjoy a boat tour, stroll along the lakefront, explore the charming downtown area, and indulge in shopping and dining.

7. Michigan City, Indiana

Located approximately 50 miles southeast of Chicago, Michigan City offers a scenic lakefront with sandy beaches, a lighthouse, and the popular Indiana Dunes State Park. Spend the day relaxing on the beach, visit the historic lighthouse, or explore the dunes and trails at the state park. You can also try your luck at the Blue Chip Casino or enjoy shopping at the Lighthouse Place Premium Outlets.

8. Door County, Wisconsin

Located about 150 miles north of Chicago, Door County is a charming peninsula known for its scenic beauty, picturesque coastal villages, and outdoor activities. Explore lighthouses, orchards, and wineries, and enjoy activities like kayaking, hiking, and biking.

9. Geneva Lake Shore Path, Wisconsin

Take a trip to the shores of Geneva Lake in Wisconsin, about 80 miles northwest of Chicago. The Geneva Lake Shore Path is a scenic walking trail that stretches for 21 miles around the lake, offering stunning lake views, beautiful gardens, and magnificent lakefront mansions.

10. Matthiessen State Park, Illinois

Located about 100 miles southwest of Chicago, Matthiessen State Park is a hidden gem with its unique rock formations, waterfalls, and wooded trails. Enjoy hiking through canyons, exploring the natural beauty, and discovering picturesque spots for photography.

These day trips provide a range of experiences, allowing you to immerse yourself in nature, explore history and architecture, enjoy lakefront activities, and indulge in the charm of nearby towns and parks.

Things to know before your Chicago Day Trip

Before you head out and drive to these exciting destinations, be sure that you are well-prepared for your day trips. Here are some important reminders to keep in mind before embarking on your Chicago road trips.

1. Plan your itinerary ahead of time – While spontaneous or surprise trips are amusing, getting lost or encountering road emergencies is not. It is always better to be prepared and organized, so you know where to go and what to expect on your day trip.

2. Keep charged – Make sure you have enough battery and storage on your phone for taking pictures and making calls. Carry a phone charger or power bank with you, as well.

3. Stay fueled – Fill up your car with gas and check the vehicle’s condition before driving. Make sure that your car is in tip-top shape and can handle long driving. With new and exotic rental cars, however, there is no need to worry because they are well-maintained and fully checked before they are handed off to you.

4. Plenty of stops – Make stops for eating, bathroom breaks, or napping if necessary. Especially if you have plenty of time and you are not following a strict schedule, be okay with stopping for a bite or driving breaks. If you are sleepy or tired from driving, stop to take a nap before continuing to your next destination.

5. Follow the rules – Follow road signs, especially speed limits. You wouldn’t want your trip to be ruined just because you got arrested for violating traffic rules, would you?

6. Have emergency contact numbers handy, such as towing service and the rental car company you signed with. This way, if there is any emergency, you can easily reach out for help.

7. Have fun! In case you are not able to arrive at your planned destination due to some reasons, make the most of your day and find other exciting things to do.

Going on road trips from Chicago provides an exciting opportunity to venture beyond the city’s borders and discover wonderful destinations in the surrounding region.

Whether you choose to explore the natural wonders of state parks, immerse yourself in the rich history of charming towns, or indulge in the cultural offerings of nearby cities, each day’s trip promises a unique and fulfilling experience. 

Make memories with your family and friends by going on to these day trip destinations from Chicago. Happy driving!

Things to know before you go to Chicago