Best Road Trips from Chicago

Looking to leave Chicago and hit the road? Fortunately there are many amazing places to visit in the Midwest that you can easily drive to from Chicago whether you love nature, beaches, cities or small towns. Here are the best road trips from Chicago from shorter road trips that you can visit as a day trip from Chicago to longer road trips for a weekend getaway or even a week long vacation.

(And make sure to check out my essential road trip packing list (with free printable pdf) and road trip music playlist to make sure you have all your road trip essentials before you go!)

Best Road Trips From Chicago

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Lake Geneva, Wisconsin

Distance from Chicago: 83 miles
Lake Geneva Wisconsin road trips from Chicago
Lake Geneva is a resort city on the shores of Geneva Lake in southeastern Wisconsin. The area is a popular vacation destination for Chicago – wealthy Chicagoans built their mansions here during the Gilded Age.

Visitors can enjoy a variety of outdoor activities on the water, including boating, kayaking, paddle boarding, and cruises. There are also a petting zoo, waterpark, golf, hiking, zip-lining, spas, and more.

The highlight is the Lake Geneva Shore Path, a a 21-mile trail around the lake with stunning views of the forest, water and impressive waterfront homes. Visitors can hike, bike or take a cruise around the lake.

Starved Rock State Park, Oglesby, Illinois

Distance from Chicago: 95 miles
Address: 2668 East 873 Road, Oglesby, IL 61348

Starved Rock State Park is one of the best roadtrips from Chicago

Starved Rock State Park is one of the top attractions in the state of Illinois. The park is an ideal spot to enjoy nature and is filled with stunning sandstone canyons and beautiful waterfalls. This is a great place for hiking with 13 miles (21 kilometers) of trails.

In addition to hiking, visitors can enjoy outdoor activities year round, including horseback riding, ice climbing, cross-country skiing, as well as fishing, kayaking, rafting on the Illinois River.

Matthiessen State Park, Oglesby, Illinois

Distance from Chicago: 96 miles
Address: 2500 IL-178, Oglesby, Ilinois 61348

Matthiessen State Park is not as popular or crowded as nearby Starved Rock State Park (less than 3 miles away) but it is just as beautiful with similar natural features such as canyons and beautiful waterfalls. (If you visit mid July to early August, make a stop to visit and photograph the sunflower field located in the park.)

Indiana Dunes, Indiana

Distance from Chicago: 50 miles

The Indiana Dunes National Park borders the State Park of the same name. The national park offers 15 miles of shoreline along Lake Michigan’s southern shore with wide sandy beaches and towering dunes. Hikers will enjoy 50 miles of trails over rugged dunes, mysterious wetlands, sunny prairies, meandering rivers and peaceful forests.

The three highest sand dunes are all in the Indiana Dunes State Park.

In addition to beaches and hiking, Indian Dunes offers many outdoor year round activities including bird watching, fishing, cycling, horseback riding, kayaking and paddling, snowshoeing, and cross country skiing.

Milwaukee, Wisconsin

Distance from Chicago: 93 miles

This lively city is like a smaller less touristy version of Chicago.

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Rockford, Illinois

Distance from Chicago: 85 miles northwest from Chicago
Anderson Japanese Gardens in Rockford Illinois is one of the best short road trips from Chicago
Image credit: Anderson Japanese Gardens

The most popular attraction in Rockford is Anderson Japanese Gardens, a 12-acre Japanese garden. Other attractions include the Discovery Center Museum (a great a family museum), Nicholas Conservatory and Gardens, Burpee Museum of Natural History, Tinker Swiss Cottage Museum and the Rockford Art Museum.

Galena, Illinois

Distance from Chicago: 164 miles

Galena is short road trip from Chicago but it a great place for weekend getaway whether on a romantic trip or traveling with kids. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House.

Some things to do in Galena including shopping downtown at the many boutiques and antique stores, eating at local restaurants and wine tasting at local vineyards. Theere or explore the lush rivers and hiking trails dotted throughout the area. Galena is close to Apple River Canyon State Park, an Illinois state park, where you can go hiking, fishing and more.

Holland, Michigan

Distance from Chicago: 150 miles
Time from Chicago: 2.5 hours from Chicago

Located on the shores of Lake Michigan, the city of Holland, Michigan, which was founded by Dutch Calvinists in the late 1840s, proudly flaunts its Dutch origins, and is home to canals and a 250-year-old authentic Dutch windmill.

Holland is especially pretty in the spring when you can see colorful tulips in local gardens, parks, attractions and lining the streets. You can see millions of tulips at Veldheer Tulip Gardens. One of the mont popular times to visit is during the Tulip Time Festival, the largest tulip festival in the United States which is held every year in May (May 1 – 9 in 2021).

Historic Route 66 Road Trip in Illinois

Illinois historic route 66 sign

Distance from Chicago: 301 miles

Historic Route 66 is a classic American road trip. Don’t have time to drive Route 66 all the way from Chicago to California? You can still drive the Illinois portion of historic Route 66 from Chicago to St. Louis. If you prefer a shorter drive, you can also drive from Chicago to Pontiac or Springfield. You will drive past unique roadside attractions, classic diners, kitschy attractions and Route 66 nostalgia.

Some must see stops in Illinois along the way include:

If you are planning to do a long Route 66 road trip, I recommend this EZ66 GUIDE For Travelers, which is considered the best Route 66 guide.

Shawnee National Forest

Distance from Chicago: 300 miles

Nestled between the Mississippi and Ohio Rivers in southern Illinois, the Shawnee National Forest is full of natural beauty, making it ideal for outdoor recreation from hiking to climbing.

The stunning Shawnee National Forest landscape features woodlands. hills, lakes, creeks. rock formations, cliffs and  bluffs. You can also see wildlife such as bad eagles.

Shawnee National Forest is the best place to go hiking in Illinois with spectacular views. Trails include the long River to River Trail and the Rim Rock National Recreational Trail. The must see attraction is the Garden of the Gods wilderness area featuring ancient sandstone cliffs and formations.  Climbers should not miss the Jackson Falls climb on 60 feet of sandstone cliffs and boulders that include numerous freestanding towers.

If you enjoy wine, The Shawnee Hills Wine Trail features 11 wineries located along a 35-mile scenic drive along highway 127 and highway 51 in the Shawnee National Forest. 

What are your favorite road trips from Chicago?

Planning a trip to Chicago? Check out my Chicago guides and itineraries:


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