Easy Illinois Road Trips and Weekend Getaways

If you live in Illinois or plan to visit, there are numerous road trip destinations that make for an incredible escape. From bustling cities to charming small towns and tranquil natural parks, here are some of the best road trip destinations within and around Illinois. Some of these places are perfect for an entire weekend getaway (or longer), and some can be fantastic day trips. All of them are just an easy drive away!

The Midwest region offers diverse and exciting destinations to cater to every interest. Whether you’re a family seeking a fun-filled day trip, a couple looking for a romantic getaway, or a group of friends aiming for an adventurous outdoor retreat, we’ve got a place for you. Many of the places are fun to visit all year round, not just in summer or fall.

Known for its bold architecture, Chicago is a city with a rich history, diverse food scene, vibrant culture, and shopping venues. The Windy City is undoubtedly one of the best weekend getaways in Illinois.

A walk around Millennium Park and a photo with the famous Cloud Gate (also known as “The Bean”) are a must. Spend your day exploring the Art Institute of Chicago, the Field Museum, and Museum of Science and Industry if you are a museum lover.

Don’t forget to explore the food scene in Chicago, from the iconic deep dish pizza to a plethora of international offerings. Our favorite restaurants in the city are Ming Hin, Girl & the Goat, and Kai Zan.

Visiting Springfield is one of the top things to do in Central Illinois, especially for those who are interested in history. This city can easily be done as a day trip.

Step into the past as you stroll through the Lincoln Home National Historic Site, and learn about his life and legacy through immersive exhibits at the Abraham Lincoln Presidential Library and Museum. Also worth a visit is the Illinois State Museum, which showcases the state’s natural, cultural, and artistic heritage.

Visiting Galena will transport you back to the 19th century. This picturesque town, tucked away in the northwest corner of Illinois, captures visitors’ hearts with its beautifully preserved architecture and vintage charm. Don’t forget to visit the Ulysses S. Grant Home while there.

The lively Main Street of Galena is known as the best Main Street in the Midwest for good reason. As you wander through it, you’ll find many boutique shops, cozy restaurants, and art galleries housed in historic buildings.

Known for its magnificent rock formations and breathtaking waterfalls, Starved Rock State Park is an oasis offering an escape from the hustle and bustle of city life. It is perfect for both outdoor enthusiasts and families. You can opt for a day trip or an overnight stay at the Starved Rock Lodge.

Hiking is the star activity here, with miles of well-marked trails catering to all levels of fitness. Each trail offers unique scenery. Whether you come for an easy or challenging hike, wildlife spotting, or simply soaking up the beauty around you, this state park promises a memorable trip. We particularly enjoy coming here in fall for the foliage colors.

5. Matthiessen State Park, IL

Matthiessen State Park is right next to Starved Rock State Park, and is often overshadowed by its neighbor. It also features trails through beautiful canyons and waterfalls. Matthiessen State Park is a perfect weekend escape whether you’re interested in hiking, birdwatching, or just want a nice picnic spot.

6. Shawnee National Forest, IL

Covering a large part of southern Illinois, the Shawnee National Forest offers a variety of outdoor activities such as hiking, horseback riding, and rock climbing. Don’t miss the Garden of the Gods for stunning rock formations and panoramic views of the surrounding forest. The Garden is also a well-known fall foliage spot in the state.

A short drive southeast from Illinois will take you to Turkey Run State Park. Hiking is the main activity at the park, with trails varying in difficulty, winding through dramatic sandstone gorges. Additionally, the Sugar Creek, which flows through the park, is a popular spot for canoeing or kayaking.

A short drive to the east of Illinois, you will discover a different landscape at Indiana Dunes National Park and State Park. This is the place in the Midwest where you can see sandy beaches usually associated with coastal destinations.

The beaches of Indiana Dunes are perfect for a refreshing dip, a leisure walk, or simply soaking up the sun. Hiking enthusiasts will love the 50 miles of trails that lead through large sand dunes, quiet woodlands and sunny prairies.

To the north of Illinois, Lake Geneva is a tranquil weekend getaway with a blend of numerous outdoor activities, peaceful landscapes, and charming town life. It is one of our most favorite small towns in the Midwest. We highly recommend the Lake Geneva Ziplines which are very beautiful in fall.

We also enjoyed the Geneva Cruise Line boat tour on the lake with views of beautiful lakeside mansions, many of which were built by wealthy Chicagoans. The tour also includes a visit to the Black Point Estate and Gardens.

Indianapolis, the capital of Indiana is a short drive southeast from Illinois. This city may serve as a nice stopover during the longer road trip toward the Smoky Mountains in Tennessee. Downtown Indianapolis buzzes with life, boasting a range of attractions to cater to various interests.

Main attractions include the Canal Walk, the Indiana State Museum, and the Indianapolis Museum of Art. Families will love the Children’s Museum of Indianapolis and the Indianapolis Zoo with the dolphin show being its highlight.

Drive a little further southeast from Indianapolis, and you’ll find yourself in Cincinnati, Ohio. History lovers will definitely need to visit the National Underground Railroad Freedom Center, a poignant tribute to the heroes of the Underground Railroad. The Cincinnati Zoo & Botanical Garden, one of the oldest zoos in the United States, is a family-friendly attraction in the city.

Food lovers may want to try the local’s take on chili, known as the Cincinnati chili. Graeter’s Ice Cream is also a local favorite.

If you are into tennis like us, Mason, which is just 30 minutes from Cincinnati, hosts the Cincinnati Open tennis tournament annually in August. Mason also has very good Lebanese restaurants, such as Aladdin’s.

Traveling southwest from Illinois, you’ll find St. Louis, Missouri. This city offers a variety of experiences that cater to all tastes. It is known for the iconic Gateway Arch, and a ride to the top will give visitors stunning views of the city.

For art enthusiasts, the Saint Louis Art Museum hosts an extensive collection. The museum building itself and its surroundings are beautiful. We also highly recommend the Missouri Botanical Garden. You may also want to visit one of the family-owned restaurants in The Hill, a long-established Italian-American neighborhood in St. Louis.

These Illinois road trip destinations are wonderful choices for either long getaways, weekend escapes, or day trips. They are suitable for families, couples, groups of friends, and solo adventurers alike. It’s all about your personal preferences, your pace, and what you want to explore.

We hope our guide to some of the best easy road trips and getaways in and around Illinois will be useful to you. Safe travels!