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Hidden gem weekend trips from Chicago

Discover the lesser-known weekend getaways just a stone's throw from the Windy City.

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

Chicago's vibrant energy is infectious, but every so often, the soul craves a quieter retreat. If the city's towering skyscrapers and bustling streets have you yearning for a change, you're in for a treat. Here's a deep dive into some of the Midwest's most enchanting escapes that remain under the radar.

Starved Rock State Park, Illinois

Nestled along the serene Illinois River, Starved Rock State Park is a sanctuary of natural beauty. The park boasts over 13 miles of trails that wind through canyons, past shimmering waterfalls, and atop scenic overlooks. Each season paints the park in a different hue, from the vibrant autumnal colors to the frozen winter landscapes. Whether you're an avid hiker or someone who simply wants to bask in nature's tranquility, Starved Rock promises a rejuvenating experience. 

Galena, Illinois

Galena is like stepping into a different era. This historic town, with its well-preserved 19th-century buildings, offers a nostalgic journey through time. As you wander the cobblestone streets, you'll discover boutique shops offering unique crafts, antiques, and artisanal products. The town's rich history is palpable, with numerous museums and tours that shed light on its storied past. And when the sun sets, the town's cozy bed and breakfasts offer the perfect retreat, often with panoramic views of the rolling hills. 

New Glarus, Wisconsin

New Glarus is a slice of Switzerland in the heart of the Midwest. This delightful town, often referred to as "America's Little Switzerland," is a testament to its founders' Swiss heritage. From chalet-style buildings to traditional festivals, New Glarus embraces its roots with pride. Foodies will revel in the authentic Swiss cuisine, while beer enthusiasts shouldn't miss a tour of the New Glarus Brewing Company. The town's scenic backdrop of green meadows and gentle hills completes the European experience. 

Saugatuck, Michigan

Art and nature converge in the coastal town of Saugatuck. Known for its vibrant arts scene, Saugatuck is dotted with galleries showcasing local and international artists. The town's cultural calendar is bustling, with art fairs, theater productions, and music festivals throughout the year. But it's not just about the arts. Saugatuck's Oval Beach is often ranked among the best in the country, offering golden sands and clear waters. And for a touch of adventure, the dune rides offer exhilarating views and a rush of adrenaline. 

Madison, Wisconsin

Madison, the capital of Wisconsin, is a city that seamlessly blends urban sophistication with small-town charm. Its downtown area, sandwiched between two lakes, offers a plethora of activities. The Dane County Farmers' Market is a must-visit, offering fresh produce and artisanal products. Meanwhile, the Memorial Union Terrace, with its iconic sunburst chairs, is the perfect spot to unwind and soak in the views. Madison's eclectic mix of shops, restaurants, and bars ensures there's something for everyone.

Indiana Dunes National Park, Indiana

Stretching along the southern tip of Lake Michigan, Indiana Dunes National Park is a mesmerizing blend of dunes, forests, wetlands, and rivers. The park's expansive sandy shores are a haven for sunbathers and swimmers in the summer, while its intricate trail system beckons hikers and nature enthusiasts year-round. The diverse habitats within the park are home to over 350 bird species, making it a birdwatcher's paradise. As you explore, you'll be treated to panoramic views of Lake Michigan, and if you're lucky, you might even spot some of the park's native wildlife. 

Bishop Hill, Illinois

A tribute to its Swedish settlers, Bishop Hill is more than just a village; it's a living museum. Established in the mid-1800s by Swedish immigrants, the village has retained its old-world charm. The community's commitment to preserving its heritage is evident in the meticulously maintained historic buildings, museums, and traditional events. From folk music festivals to arts and crafts fairs, Bishop Hill offers a cultural immersion like no other. And when it comes to food, the village's eateries serve up delectable Swedish dishes that'll have you coming back for more. 

Door County, Wisconsin

Often dubbed the "Cape Cod of the Midwest," Door County is a picturesque peninsula that promises a blend of nature, culture, and relaxation. Its 300 miles of shoreline are dotted with lighthouses, quaint fishing villages, and serene beaches. The county is renowned for its cherry orchards, and a visit during the cherry blossom season is a visual treat. Art enthusiasts will appreciate the myriad galleries and studios, while food lovers can indulge in the region's fresh fish boils and cherry pies. Whether you're kayaking in its clear waters or simply enjoying a sunset, Door County is pure magic. 

Spring Green, Wisconsin

Spring Green is where architecture and nature dance in harmony. The town's claim to fame is Frank Lloyd Wright's Taliesin, a testament to the architect's genius. This sprawling estate offers guided tours that delve into Wright's life and work. But there's more to Spring Green than just Taliesin. The House on the Rock, with its eccentric collections and architectural marvels, offers a whimsical journey that's bound to leave you in awe. Surrounded by lush landscapes and the meandering Wisconsin River, Spring Green is a fusion of creativity and natural beauty. 

Shawnee National Forest, Illinois

Tucked away in southern Illinois, Shawnee National Forest is a rugged expanse of unparalleled beauty. The forest's diverse landscapes, from its rocky bluffs to its dense woodlands, offer a visual treat at every turn. Popular spots like the Garden of the Gods and Little Grand Canyon offer breathtaking vistas that showcase the region's geological wonders. Whether you're horseback riding, rock climbing, or simply camping under the stars, Shawnee National Forest offers an immersive nature experience that rejuvenates the spirit.

In the heart of the Midwest, these hidden gems offer a refreshing contrast to Chicago's urban sprawl. Each destination, with its unique charm and allure, beckons travelers to explore and discover. So, the next time the city lights feel a tad too bright, remember that these tranquil escapes are just a short drive away. Here's to new adventures and memories waiting to be made. Safe travels!


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

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