City guides

Best weekend trips from Chicago

Dive into the allure of the Midwest with our curated list of weekend escapes from the heart of Chicago.

September 19, 2023
 min read
Last updated:
Jan 15
A view of the Chicago skyline, with the Chicago river in the foreground.

With its iconic skyline, deep-dish pizzas, and bustling streets, Chicago is a city that never ceases to amaze. But every now and then, even the most die-hard Chicagoans need a change of scenery. Whether you're craving a serene lakeside retreat or an adventurous hike, we've got you covered. Dive into our handpicked list of the top weekend destinations that promise a refreshing escape from the urban jungle.

Galena, Illinois

Galena, a picturesque town in Northwestern Illinois, is like stepping into a time capsule. Its beautifully preserved 19th-century architecture and cobblestone streets evoke a sense of nostalgia. The town's rich history is evident in every corner, from the Civil War-era homes to the old-fashioned trolley rides. As you wander through Galena's charming Main Street, you'll find an array of boutique shops, artisanal eateries, and cozy cafes. For wine enthusiasts, the local wineries offer a delightful opportunity to sample regional flavors. A weekend here is a journey back in time, coupled with modern comforts.

Lake Geneva, Wisconsin

A stone's throw from Chicago, Lake Geneva is a haven for water lovers. The shimmering lake, surrounded by opulent mansions and lush forests, is the town's crown jewel. Visitors can embark on boat tours, offering panoramic views of the landscape, or engage in water sports like jet skiing and paddleboarding. The town itself is bustling with activity. From gourmet restaurants to quirky boutiques, there's something for everyone. And if you're visiting in the colder months, the snow-covered vistas transform Lake Geneva into a winter wonderland, perfect for skiing and snowboarding. 

Starved Rock State Park, Illinois

Nature enthusiasts, rejoice! Starved Rock State Park is a testament to Illinois' diverse landscapes. The park boasts over 13 miles of trails, leading to awe-inspiring canyons and cascading waterfalls. Each season paints the park in different hues, from the fiery reds and oranges of fall to the vibrant greens of spring. Wildlife sightings, including deer and eagles, add to the park's allure. After a day of hiking, visitors can relax at the park's lodge, which offers rustic accommodations and a warm ambiance. It's a wild escape, right in the heart of the Midwest. 

New Buffalo, Michigan

New Buffalo, often dubbed the 'Riviera of the Midwest', is a coastal gem. Its expansive sandy beaches are perfect for sunbathing, beach volleyball, or simply watching the waves roll in. The town's harbor is a hub of activity, with yachts and fishing boats dotting the landscape. Seafood lovers are in for a treat, with restaurants serving up fresh catches daily. For the adventurous, water sports like windsurfing and parasailing are readily available. As the sun sets, the town's vibrant nightlife comes alive, with live music and bonfires lighting up the beach. 

Saugatuck, Michigan

Saugatuck is a celebration of art and nature. Known for its thriving arts scene, the town is home to numerous galleries, studios, and theaters. Art aficionados can spend hours exploring the works of local artists or even participate in workshops. But Saugatuck's allure doesn't end there. The nearby dunes offer thrilling rides, while the town's breweries serve up craft beers that are a hit with locals and tourists alike. The Kalamazoo River, which winds through the town, offers opportunities for kayaking and boat rides, making Saugatuck a blend of cultural and natural experiences. 

Madison, Wisconsin

Madison, Wisconsin's capital, is a vibrant city that seamlessly blends urban sophistication with natural beauty. The iconic State Capitol building, with its stunning architecture, is a must-visit. Surrounding it is State Street, a lively stretch filled with shops, cafes, and street performers. Madison's location between two lakes means water activities are aplenty. From paddleboarding to lakeside picnics, there's no shortage of ways to enjoy the water. The city's eclectic food scene, with its farm-to-table restaurants and bustling farmers' markets, ensures that every meal is an experience in itself. 

Door County, Wisconsin

Door County is a picturesque peninsula where nature and culture intertwine. Its cherry orchards are legendary, with the annual cherry blossom season drawing visitors from far and wide. The county's coastline, dotted with lighthouses and quaint towns, offers breathtaking views of Lake Michigan. Activities range from kayaking in the serene waters to attending local theater productions. The county's Scandinavian heritage is evident in its festivals, architecture, and cuisine. Whether you're picking cherries, savoring a traditional fish boil, or simply watching the sunset, Door County offers a slice of the good life. 

Indiana Dunes National Park, Indiana

Stretching along the southern tip of Lake Michigan, Indiana Dunes National Park is a landscape of contrasts. Its towering sand dunes, some reaching heights of over 200 feet, offer panoramic views of the lake and are a favorite among hikers. The park's diverse ecosystems, from wetlands to forests, are home to a plethora of flora and fauna. Birdwatchers can spot over 350 species, making it a birding paradise. The park's beaches are perfect for relaxation, while the nearby towns offer a glimpse into the region's history and culture. 

Springfield, Illinois

Springfield, the heart of Illinois, is steeped in history. As the home of Abraham Lincoln, the city offers numerous sites dedicated to the 16th president, from his family home to his presidential library and museum. But Springfield's charm goes beyond its historical sites. The city's vibrant downtown, with its eclectic mix of shops, restaurants, and bars, pulsates with energy. Events like the Illinois State Fair and the Route 66 Festival showcase the city's cultural richness. A trip to Springfield is a journey through time, with a touch of modern flair. 

Mackinac Island, Michigan

Mackinac Island is a place where time seems to stand still. With motor vehicles banned, the island's mode of transport is bicycles and horse-drawn carriages. The island's Victorian architecture, lush gardens, and fudge shops give it a unique charm. Activities range from horseback riding to exploring the historic Fort Mackinac. The island's Grand Hotel, with its sprawling porch, is a sight to behold. Whether you're attending the annual Lilac Festival or simply taking in the views from Arch Rock, Mackinac Island promises a truly timeless experience.

So, when the hustle of Chicago beckons for a breather, these destinations await with open arms. Each offering a unique tapestry of experiences, they're a testament to the Midwest's rich tapestry. Pack your bags, hit the road, and let the adventures begin. Safe travels!

*Prices fluctuate based on season and day of the week.

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