The 14 Best Weekend Getaways From Chicago

Planning a weekend escape from the bustling city of Chicago can be an exciting adventure, offering diverse landscapes and experiences. Anyone looking for a refreshing break will find options that cater to nature lovers, history enthusiasts, and those seeking relaxation.

With an array of destinations just a short drive away, travelers can enjoy scenic views, charming towns, and a variety of activities. Each getaway offers a unique vibe, ensuring that there’s something for everyone. Whether it’s exploring a nearby state park or delving into the culture of a historic town, these trips promise memorable moments just a weekend away.

Saugatuck, Michigan

Our Rating: 9.0/10

Saugatuck, a charming town on the shores of Lake Michigan, offers a perfect weekend escape. Visitors can explore its vibrant art galleries and quirky curio shops. The town’s creative spirit is evident in every colorful corner.

Outdoor enthusiasts can enjoy Saugatuck Dunes State Park. Hike through trails that wind through dunes and forests, leading to stunning lake views. It’s an adventure for nature lovers. For a taste of local flavors, Saugatuck boasts cozy restaurants and vineyards. Visitors can savor fresh local dishes and sample regional wines. The welcoming atmosphere and scenic beauty make it a must-visit spot.

Indiana Dunes National Park, Indiana

Our Rating: 8.5/10

Indiana Dunes National Park offers a captivating escape just an hour from Chicago. With 15 miles of Lake Michigan shoreline, visitors can enjoy sunbathing or swimming. The vast sandy beaches are perfect for relaxation or a lively beach day.

Adventurers can explore 50 miles of scenic trails. These paths wind through dunes, wetlands, and forests, making them ideal for hiking. Nature lovers will find diverse ecosystems filled with unique plants and wildlife. Camping is another popular activity, allowing overnight guests to experience the tranquil beauty of the park under a starlit sky. Prepare to be enchanted by this wonderful slice of nature near the urban hustle of Chicago.

Starved Rock State Park, Illinois

Our Rating: 8.7/10

Starved Rock State Park, a natural gem along the Illinois River, is perfect for those craving adventure. With over 13 miles of scenic trails, the park invites visitors to hike through 18 sandstone canyons and marvel at 14 stunning waterfalls. Each season brings its own charm, from lush summer greenery to winter’s icy cascades.

Fishing and boating are popular activities on the Illinois River, offering relaxation and a chance to connect with nature. For those looking for a peaceful escape, the park provides plenty of spots to relax and soak in breathtaking views. Just a short drive from Chicago, Starved Rock is a must-see for nature lovers.

Lake Geneva, Wisconsin

Our Rating: 8.5/10

Lake Geneva is a charming retreat just a short drive from Chicago. Visitors can stroll the scenic Geneva Lake Shore Path. This 26-mile route offers views of beautiful mansions and lush greenery. For those who enjoy water activities, the lake invites guests to try boating or fishing. Plenty of rentals and guided tours are available.

Downtown Lake Geneva is lively with boutique shops and cozy cafes. The local restaurants serve delightful dishes, capturing the spirit of Wisconsin’s culinary scene. Whether exploring nature or enjoying shopping and dining, Lake Geneva promises a refreshing break from city life.

Galena, Illinois

Our Rating: 9.3/10

Galena, Illinois, is a charming destination with plenty of activities and sights to explore. Known for its well-preserved 19th-century buildings, the town offers a journey back in time with its historic Main Street filled with boutique shops and cozy cafes. Visitors can unwind at local wineries offering delightful tastings and picturesque vineyard views.

For outdoor enthusiasts, renting an electric bike to explore the rolling hills provides a unique way to experience the scenic landscape. History buffs will appreciate the Ulysses S. Grant Home, offering a peek into the past of the famous Civil War general and U.S. President. With its combination of history, relaxation, and adventure, Galena is an enticing weekend getaway from Chicago.

Milwaukee, Wisconsin

Our Rating: 8.3/10

Milwaukee is a vibrant city perfect for a weekend escape from Chicago. Visitors can explore the bustling Historic Third Ward, known for its lively art galleries, trendy boutiques, and delicious dining options. The Milwaukee Public Market offers local flavors and unique finds.

Nature lovers will appreciate Lakeshore State Park, a serene spot for jogging, biking, or simply enjoying views of Lake Michigan. The nearby Milwaukee Art Museum, with its stunning architecture, entices art enthusiasts with a vast collection. For beer aficionados, a tour of Milwaukee’s famous breweries is a must. Sampling craft beers at iconic spots offers a taste of the city’s rich brewing history.

Grand Rapids, Michigan

Our Rating: 8.5/10

Grand Rapids, known as “Beer City USA,” offers a delightful experience for craft beer enthusiasts. With over 80 breweries to explore, it’s a paradise for those who enjoy a good pint. Art lovers will appreciate the Grand Rapids Art Museum and the Frederik Meijer Gardens & Sculpture Park. These spots offer stunning artworks and vibrant flora.

For outdoor adventures, the John Ball Zoo and Millennium Park provide a mix of wildlife encounters and beautiful trails. They offer a refreshing escape into nature. Foodies will love the local dining scene, which ranges from artisanal bakeries to eclectic restaurants. Each bite in Grand Rapids promises a unique taste of Michigan.

Harbor Country, Michigan

Our Rating: 8.5/10

Harbor Country, Michigan, is a haven for those seeking a peaceful escape by shimmering waters. Visitors can explore the charming lakeside towns that boast rich scenic beauty and quaint shops. Each town offers unique experiences sure to delight weekend travelers.

New Buffalo stands out for its sandy beaches perfect for sunbathing or enjoying a relaxing picnic by Lake Michigan. It’s a hotspot for boating and water sports, offering both excitement and leisure. Union Pier captures hearts with its rustic charm, where boutique shops and local eateries create a cozy atmosphere. Nature lovers can head out on hiking trails or rent bikes to view the picturesque countryside.

Columbus, Indiana

Our Rating: 8.5/10

Columbus, Indiana, stands out with its striking architectural designs. Visitors often find themselves captivated by the modern buildings crafted by renowned architects. The city feels like an open-air museum, where each structure tells its own story. Exploring Mill Race Park is a must for nature lovers. It’s a serene spot for a picnic or leisurely walk with picturesque views of the river.

The park also hosts various events, adding a lively energy to this peaceful setting. Visitors can dive into local culture at the Commons, a vibrant community space featuring an indoor playground and public art displays. Columbus offers a delightful blend of culture, architecture, and natural beauty, making it a unique destination.

Wilmot Mountain, Wisconsin

Our Rating: 8.5/10

Wilmot Mountain is a charming escape just an hour and a half from Chicago. Enthusiasts flock here to carve through 25 thrilling trails spread over 120 acres. Each trail offers its own excitement, from beginner-friendly slopes to adventurous runs for seasoned skiers.

Skiing isn’t the only draw. Visitors can also enjoy snow tubing for a different kind of thrill. The multiple terrain parks cater to freestyle riders looking to perfect their tricks. Beyond the slopes, a cozy eatery serves as a perfect spot to relax and warm up. It’s a delightful destination that mixes adrenaline-pumping action with relaxing downtime.

Amish Country, Indiana

Our Rating: 8.3/10

Nestled in the heart of Indiana, Amish Country offers a peaceful escape from city life. Travelers can explore quaint family-owned shops filled with hand-crafted items. Horse-drawn buggies add charm to the rustic landscapes.

History enthusiasts enjoy visiting the many antique shops, showcasing items that tell stories of the past. The area’s famous quilt gardens, bursting with color, make for a delightful stroll. Families can spend a day exploring bustling markets, where fresh produce and baked goods tempt taste buds. The warm hospitality of the Amish community welcomes all who wander, offering a glimpse into a simpler, more tranquil way of life.

Louisville, Kentucky

Our Rating: 8.3/10

Louisville stands out as a fascinating getaway with its energetic racing events and bourbon heritage. Visitors can dive into the thrilling experience of Churchill Downs, home of the iconic Kentucky Derby. The atmosphere is always alive with excitement, and everyone can feel the racing spirit in the air.

Wandering through the Urban Bourbon Trail is a must. It offers a fantastic chance to taste and explore the rich flavors of Kentucky’s finest bourbons. The trail is filled with warm hospitality and unique tales of distilleries. For a quieter pace, the Louisville Waterfront Park provides scenic views and peaceful walks along the Ohio River. It’s the perfect spot for relaxation and taking in the natural beauty of the area.

Indianapolis, Indiana

Our Rating: 8.5/10

Just a few hours from Chicago, Indianapolis offers a captivating blend of culture and fun. Visitors can start by exploring the Indianapolis Motor Speedway Museum, where the thrill of racing comes alive with fascinating exhibits and historic cars. In the heart of the city, the Indianapolis Museum of Art at Newfields boasts stunning galleries surrounded by beautiful gardens.

For those who love history, the Indiana State Museum provides engaging exhibits about the state’s rich past. Outdoor enthusiasts can stroll along the Canal Walk, a serene pathway that winds through downtown. Meanwhile, food lovers will find a vibrant culinary scene at the famous St. Elmo Steak House, serving mouthwatering steaks in a classic setting.

South Haven, Michigan

Our Rating: 8.5/10

South Haven is a charming coastal town on Lake Michigan, perfect for a weekend escape. Visitors can enjoy walking along the sandy beaches, where the waves gently lap the shore. Breathtaking sunsets paint the sky in vibrant hues, offering picture-perfect moments.

Downtown, there are quaint boutiques offering unique finds, while the local cafes serve delicious treats. The area is also known for its lush vineyards and wineries, inviting guests to indulge in some wine tasting. For outdoor lovers, the Kal-Haven Trail is a popular spot for hiking and biking through scenic landscapes. South Haven’s art galleries showcase local talent, adding a cultural touch to the trip.

Chicago’s proximity to a variety of unique destinations makes it easy to escape the city for a weekend and recharge. Whether you’re interested in exploring quaint small towns, enjoying nature, or indulging in regional cuisine, these getaways offer the perfect opportunity to break away from the routine and create lasting memories.