8 Unforgettable Weekend Trips From Chicago
The city lights of Chicago can shine so brightly that they sometimes eclipse the unexpected wonders just a few hours away. Yet, beyond the skyscrapers lie destinations that offer a complete change of pace without sacrificing culture, history, or enjoyment.
Instead of settling for the usual museum visits or deep-dish pizza stops in the Windy City, step into tucked-away towns, serene lakeshores, and vibrant communities that few travelers think to explore. Each of these eight spots boasts its own story, attractions, and inviting atmosphere, tempting you to leave behind the familiar skyline for a fresh, unforgettable experience.
Shipshewana, Illinois
- Driving Time: 2hrs 30mins
Shipshewana is a small town steeped in Amish culture, making it an intriguing escape just over two hours from Chicago. Known for its rich history of Amish craftsmanship and serene landscapes, this town offers a distinctive blend of peaceful rural atmosphere with traditional Amish experiences. The Menno-Hof Amish/Mennonite Information Center provides a comprehensive look at Amish and Mennonite history through immersive exhibits and tours that explain their origins and lifestyle. Visitors can explore the Shipshewana Auction & Flea Market, the largest of its kind in the Midwest, featuring hundreds of vendors selling everything from handmade quilts to fresh produce. Dining options include the Blue Gate Restaurant, where one can savor homemade Amish meals and bakery goods. For accommodation, the Farmstead Inn & Conference Center offers comfortable lodging right across from the flea market, providing modern amenities with a touch of country charm. Nearby, the Shipshewana Trading Place allows visitors to experience live auctions, adding an authentic local flavor to the visit.
Galena, Illinois
- Driving Time: 3hrs 10mins
Galena, Located in the northwest corner of the state, is known for its rich history as a lead mining town. This scenic town was once home to Ulysses S. Grant and today, visitors can explore the Ulysses S. Grant Home State Historic Site, where the former president once lived. The Galena River, which runs through the town, enhances its picturesque setting. For those looking to explore local culture, Main Street in Galena is lined with boutiques, art galleries, and eateries such as Otto's Place, which offers local cuisine. The DeSoto House Hotel, established in 1855 and still operational, provides historical accommodation right in the heart of downtown. Nearby, Grant Park offers peaceful views and a glimpse into the town's historic architecture and monuments.
Lake Geneva, Wisconsin
- Driving Time: 2hrs
Lake Geneva is renowned for its stunning lake views and grand estates that line its shores. Originally a retreat for wealthy Chicago families after the Great Chicago Fire, this lake town boasts a rich history of opulence and leisure, exemplified by the well-preserved architecture and lush landscapes. Notably, the town's public path allows visitors to explore the historic lakeside estates up close.
Activities in Lake Geneva cater to a range of interests. For adventure seekers, Lake Geneva Canopy Tours offers ziplining experiences through the dense forests. History enthusiasts may visit the Geneva Lake Museum to delve into the area’s past. Dining options include Sopra Bistro, known for its contemporary American dishes. For accommodation, the Grand Geneva Resort & Spa provides luxury lodging with extensive amenities including golf courses and a spa, ensuring a comfortable stay year-round. The resort’s active calendar features events and seasonal activities, enhancing any weekend getaway.
Indiana Dunes National Park, Indiana
- Driving Time: 1 hr
Indiana Dunes National Park, located on the southern tip of Lake Michigan just an hour from Chicago, offers a unique landscape of dunes, wetlands, prairies, and forests. Established as a national park in 2019, it spans 15,000 acres and provides a haven for biodiversity and conservation efforts. Visitors can explore over 50 miles of trails, including the challenging 3 Dune Challenge.
For those interested in relaxing or bird-watching, the park's extensive beaches are ideal. Nearby, the town of Chesterton offers dining options like Octave Grill, known for its craft burgers. For overnight stays, Riley’s Railhouse Bed & Breakfast in Chesterton provides a unique lodging experience in a converted train station.
Traverse City, Michigan
- Driving Time: 5hrs
Traverse City, known for its pivotal role in America's cherry industry, is a delightful destination north of Chicago on the shores of Lake Michigan. This city hosts the esteemed National Cherry Festival each summer, drawing visitors from all over. Traverse City's vibrant downtown is filled with unique shops and restaurants like The Cooks' House, celebrated for its local cuisine.
A scenic drive through Michigan to get to Traverse city includes stops in South Haven and Cedar Springs, which are perfect for sightseeing and rest. In Traverse City, the Dennos Museum Center offers engaging art and science exhibitions. Stay at the Hotel Indigo Traverse City, which provides waterfront views and modern amenities, ensuring a pleasant visit.
St. Joseph, Michigan
- Driving Time: 2hrs
St. Joseph, positioned on the shores of Lake Michigan, is known for its picturesque lighthouse and family-friendly beaches. This small town is celebrated for its role in regional maritime history and its vibrant arts scene, including the Krasl Art Center, which hosts outdoor sculptures and exhibitions. Visitors can explore Silver Beach County Park, known for its clean, sandy beaches and the nearby Silver Beach Carousel. Dining options include The Buck Burgers & Brew, which offers gourmet burgers and a vast selection of craft beers. The Boulevard Inn & Bistro provides comfortable rooms with views of the lake and downtown, ensuring a convenient and relaxing stay.
Saugatuck, Michigan
- Driving Time: 2hrs 30mins
Saugatuck is a serene retreat on the shores of Lake Michigan. This quaint town has a rich history as an artists' colony, which continues to influence its vibrant cultural scene today. Visitors can explore unique galleries like the Amazwi Contemporary Art Gallery, which showcases African art and artists. Outdoor enthusiasts can enjoy Oval Beach, renowned for its pristine sands and sunset views. The Southerner offers authentic Southern-inspired dishes right by the water. The Saugatuck Retro Resort Motel provides a nostalgic lodging experience with updated amenities, ensuring guests a comfortable and memorable stay.
Harbor Springs, Michigan
- Driving Time: 6 hrs
Harbor Springs, located on the northern shore of Little Traverse Bay, is celebrated for its deep harbor and charming, historic architecture. This small town is known for its vibrant community and scenic beauty, making it a popular destination for sailing and skiing. The area's rich history as a summer retreat is preserved in its beautifully maintained Victorian homes. You can explore local boutiques and galleries or dine at Stafford’s Pier Restaurant, which offers waterfront dining with local seafood specialties. The Andrew J. Blackbird Museum offers insights into the area's Native American history. The Colonial Inn Hotel provides historic accommodations with modern comforts. For those driving from Chicago, consider stops in Holland, Michigan, Grand Rapids, and Petoskey to break up the long journey and enrich the travel experience.
