Discover the Best Secret Weekend Escapes Near Chicago
Chicago, known for its vibrant city life, cultural diversity, and architectural wonders, certainly has its appeal. But every now and then, a change of scenery can do wonders for the soul. Luckily, the Midwest offers a plethora of charming destinations just a short drive away. These underrated weekend getaways near Chicago promise unique experiences, whether you seek tranquil nature spots or lively local scenes.
Milwaukee, WI
Driving time from Chicago: Approximately 1.5 hours
Just a quick drive from Chicago, Milwaukee stands out with its rich brewing history, artistic venues, and welcoming atmosphere. Famous for its collection of craft beers and delectable cheeses, Milwaukee's comfort doesn't stop there.
Explore: Begin your Milwaukee adventure at the Milwaukee Art Museum, a masterpiece designed by Santiago Calatrava, showcasing nearly 25,000 art pieces. Not into art? Simply admire the structure's beauty against the Lake Michigan backdrop.
Stay: Check-in at the Kimpton Journeyman Hotel in the Third Ward district, known for its proximity to booming eateries and bars, alongside a breathtaking rooftop terrace to unwind amid the city's buzz.
Kohler, WI
Driving time from Chicago: About 2 hours and 15 minutes
This hidden gem in Wisconsin offers a unique blend of tranquility and sophisticated indulgence. Renowned for its impeccable spa services, Kohler is a sanctuary for those looking to detox from city life.
Explore: Scale the dunes at Kohler-Andrae State Park then relax at the only five-star spa in the Midwest, Kohler Waters Spa. Experience their renowned hydrotherapy circuit before exploring the charming town.
Stay: Opt for a luxurious experience at Destination Kohler, enjoying the plush accommodations of their resort or choose a cozy retreat at Velvet Sheep Farms Bed & Breakfast, where pastoral life invites you to slow down and connect with nature.
Galena, IL
Driving time from Chicago: About 3 hours
A trip back in time awaits in Galena, a historic town famous for its enchanting 19th-century architecture and quaint resorts.
Explore: Wander through over a hundred unique shops downtown or visit the historical Ulysses S. Grant Home. Time your visit with the Great Galena Balloon Race for an unforgettable experience.
Stay: Eagle Ridge Resort & Spa is your sanctuary here, offering golf courses, hiking trails, relaxed dining, and tailor-made spa treatments to complete your stay.
Indianapolis, IN
Driving time from Chicago: Around 3 hours
Despite its nickname that suggests otherwise, Indianapolis boasts an energetic vibe with its mix of eateries, cultural spots, and lively neighborhoods.
Explore: Discover the Fountain Square Cultural District, brimming with art, cozy cafes, and nightlife that includes everything from jazz to drag performances. Make time for the distinctive charm of the White Rabbit Cabaret or a swing dance at the Fountain Square Theater.
Stay: Revel in art-deco elegance at Bottleworks Hotel, housed in a former Coca Cola Bottling Plant, complete with its own food hall and local retail shops.
Madison, WI
Driving time from Chicago: About 2.5 hours
Wisconsin’s second-largest city, Madison, popularly known as “Lake City,” is a beacon for year-round outdoor fun amidst its enchanting lakes and lush parks.
Explore: Head to Olbrich Park for kayaking or snowshoe adventures, followed by a refreshing beer at Giant Jones Brewery.
Stay: The eco-friendly Hotel Indigo Madison Downtown offers easy access to dining and shopping, wrapped up in historic charm and modern comfort.
Door County, WI
Driving time from Chicago: Roughly 4.5 hours
A dreamy stretch of coastline, Door County is noted for its rustic charm, local cuisine, and breathtaking landscapes.
Explore: Start with a hearty breakfast at Blue Horse Cafe before trekking the Ice Age National Scenic Trail. Don't miss sampling the region's freshly caught fish and cherry-infused treats.
Stay: The White Gull Inn offers a homey and historic stay, accentuated with warm hospitality and a must-try breakfast featuring local flavors.
Detroit, MI
Driving time from Chicago: 4.5 hours
Detroit is going through a renaissance, combining its industrial roots with cultural and culinary vibrancy.
Explore: Relish Detroit’s rising food scene with visits to standout eateries like Selden Standard and Sister Pie. A trip to John K. King Used & Rare Books will satisfy any book lover's heart.
Stay: The Siren Hotel, situated in the historic Wurlitzer Building, not only offers chic accommodations but an intimate cocktail experience at its Candy Bar.
Des Moines, IA
Driving time from Chicago: Approximately 5 hours
This underestimated capital city of Iowa will surprise you with its vibrant arts scene, local events, and impressive public art.
Explore: Wander through the Greater Des Moines Botanical Garden and the Art Route. Plan to visit during the summer to catch iconic events like the Des Moines Arts Festival.
Stay: For a lavish stay, the Surety Hotel offers chic accommodations, while the Des Lux Hotel is the epitome of vintage glamor with cozy fireplaces and a sophisticated bar.
By uncovering these underrated destinations near Chicago, adventurers can indulge in rich cultures, exquisite leisure, and breathtaking natural beauty without straying far from the city. Plan your excursion and explore these hidden jewels of the Midwest, each offering unique slices of Americana that invigorate and inspire.
