Who doesn’t love a good road trip? One of the best things about Chicago is its central location, which makes it easily accessible to many great destinations across the Midwest. With several states within a reasonable driving distance, there is an endless number of places to choose from for your next weekend retreat or extended getaway. From charming lakeside towns less than two hours away to natural marvels in every direction, while we love our hometown of Chicago, we love to get away from it once in a while, too. Whether you’re a local or visiting, consider one of these memorable road trips for your next adventure.

Note: Drive times vary depending on the starting location in Chicago and the route.

Under 2 Hours

Milwaukee, WI - approximately 90 minutes from Chicago

Located on Lake Michigan, Milwaukee (or “Brew City”) is known for its summer festivals, being a culinary hub, and beer…lots of beer. Many people come to Milwaukee for Summerfest - the world’s largest music festival - and attractions like the Harley-Davidson Museum. Still, there’s so much more to explore throughout the streets of this culturally diverse midwestern city. Beer lovers rejoice with a bevvy of breweries to visit. Nature lovers will be satisfied with dozens of trails to bike or walk, many of which offer stunning views of Lake Michigan. Foodies will find themselves in heaven with a broad range of dining options, from casual restaurants to fine dining establishments. Food Halls like 3rd Street Market and Milwaukee Public Market offer an opportunity to experience, taste, and shop a variety of flavors and artisanal products. The walkable Historic 3rd Ward seamlessly blends the past with modern times, featuring 19th-century warehouses, waterfront patios, a vibrant art scene, and more. And while Milwaukee has an elevated dining scene, you don’t want to miss trying a Butterburger or Frozen Custard in their home city.

Lake Geneva, WI - approximately 1.5 - 2 hours from Chicago

A long-time summertime resort for affluent Chicagoans, Lake Geneva has been a seasonal destination for over a century. Known for its Gilded Age estates, water sports, nature activities, and small-town charm, it’s an excellent option for anyone looking to get away from the city without going far. Lake Geneva offers a great mix of affordable and luxury options to accommodate a range of visitors, whether they’re traveling on a budget or looking to indulge. The 21-mile Shore Path around Lake Geneva is a great opportunity to see the estates up close. The original inhabitants of the area believed the lakefront should belong to the public, leading to the creation of the Shore Path. Coincidentally, many parts of that path go through the estate grounds of mansions located on the lake, including Black Pointe Estate - built by Conrad Seipp, Hazeldore - one of the few remaining original homes that hasn’t been significantly updated, and Stone Manor - the biggest lake mansion designed by Henry Lord Gray and built for Otto Young.

Starved Rock State Park, IL - approximately 2 hours from Chicago

A destination for nature enthusiasts, Starved Rock State Park is just about two hours southwest of Chicago, known for canyons, waterfalls, and the Illinois River. Starved Rock is home to 18 sandstone canyons, most of which feature waterfalls at various times throughout the year, and scenic bluffs along the Illinois River. Having been inhabited for over 10,000 years by humans, Starved Rock has a rich Native American history that visitors can learn about during their visit. Enjoy water sports like canoeing, hiking, and fishing, or explore over thirteen miles of hiking trails throughout the park.

2-4 Hours

Saugatuck, MI - approximately 2.5 hours from Chicago

Located in southwest Michigan on the lake, Saugatuck has become a favorite retreat for many Chicagoans in recent years. Filled with art, culture, and a welcoming community, Saugatuck offers the perfect small-town atmosphere in an inclusive, diverse package. Saugatuck is one of a trio of towns in Michigan known as the “Art Coast” for its award-winning beaches, rich art culture and history, culinary hub status, and recognition as an LGBTQ destination. From sailing to biking trails, wine tastings to tacos, Saugatuck is a fantastic escape for anyone looking to get out of the city for a bit. Shop at boutique stores, visit artists, artisans, and makers, or enjoy a meal while soaking up the sunshine on one of the many vibrant patios. Saugatuck truly has something for everyone.

Galena, IL - approximately 2.5 - 3 hours from Chicago

Located in the northwestern corner of Illinois, across the Mississippi River from Iowa, Galena is a picturesque town known for 19th-century architecture and rich history. The home of Ulysses S. Grant and several other Civil War generals, Galena is considered an “architectural time capsule” for having one of the “best-preserved collections of 19th-century architecture in the United States.” Historic Main Street in Galena features a diverse range of attractions, including boutique shops, wineries, distilleries, art galleries, and even a magic theater. Choose from a variety of accommodations, from cozy bed and breakfasts to luxury resorts.

Devil’s Lake State Park, WI - approximately 3 hours from Chicago

A nature lover’s paradise, and a little farther from home, Devil’s Lake State Park near Baraboo, Wisconsin, is located along the Ice Age National Scenic Trail. This historic trail boasts 1200 miles of the state’s most extraordinary geologic and glacial features, with the oldest rocks dating over 1.6 billion years. Devil’s Lake is considered to be one of the most beautiful parts of the scenic trail. Don’t miss a chance to grab a photo near Devil’s Doorway, a spectacular rock formation looking over Devil’s Lake, and enjoy many different outdoor activities, including biking, boating, hiking, rock climbing, paddle boarding, and more.

4+ Hours

Door County, WI - approximately 4.5 - 5 hours from Chicago

Located on a peninsula between Green Bay and Wisconsin, Door County is rising in popularity as a vacation destination near Chicago. Known as the “Cape Cod of the Midwest”, Door County is home to cozy coastal small towns, a bustling art scene, vibrant culture, and stunning natural sites. Cherry trees are a popular attraction in spring for their blossoms and in summer and fall for their harvest. Spectacular calm waters from Lake Michigan make for the perfect lakeside retreat - whether you’re simply catching up on some reading while soaking in the sun, or taking a boat out for a day on the water. Tour nearly a dozen wineries, go on a hike, let your taste buds free in a flavorful culinary scene, or see a play from America’s oldest resident summer theater. Door County is the ultimate destination for those who want to be near nature but not in nature, just as much as it is for those who are looking to become one with the trees.

Charlevoix, MI - approximately 5.5 - 6 hours from Chicago

The ultimate small town getaway, Charlevoix is located less than 30 minutes South of Petoskey on an isthmus between Lake Michigan and Lake Charlevoix. Featuring friendly locals, unique fairytale homes, and more shoreline than you can possibly know what to do with, this town is small but mighty. A hub for nature lovers, bike along the lakefront, hike one of many trails, or find yourself on the water, whether by boat, catamaran, or jetski. Charlevoix boasts a vibrant art scene, a plethora of boutique shopping, and cozy cafes perfect for leisurely spending a long weekend or an extended stay. Venture less than thirty minutes up the shoreline to Petoskey or explore one of the other many small towns nearby, like Boyne City or Harbor Springs. Stop in Saugatuck, South Haven, or Benton Harbor after entering Michigan for a waterside lunch before making the final trek up to northwest Michigan.

Garden of the Gods Wilderness in Shawnee National Forest, IL - approximately 6 hours from Chicago

Not to be confused with a park of the same name in Colorado, the Garden of the Gods in Shawnee National Forest is a stunning wilderness area located near the southern tip of Illinois. While each of the Illinois-based destinations on this list is beautiful and worth a visit in its own right, Garden of the Gods is arguably the most beautiful of the state’s natural sites. According to the Shawnee Forest website, “more than 320 million years ago, the wind and rain patiently started to chisel away at large deposits of sedimentary rock…over the years, the elements have sculpted some of the most stunning and extraordinary rock formations known to man.” The Shawnee National Forest offers a variety of hiking trails to choose from. Those who are less athletically inclined or short on time can take advantage of the Observation Trail, a quarter-mile stretch that highlights some of the most scenic spots. Those interested in exploring the forest in greater depth can tackle a 5.5-mile stretch, either on foot or by horseback.