The Midwest is packed with character-filled towns, gems along Lake Michigan, and adventure hubs. Whether you crave waterfall hikes, craft brews, or lazy days on the water, these nine weekend getaways—just hours from Chicago—are worth every mile.
Featured vacation rental: Thunderbird Resort Condo, Unit 1050A
Plunge into the “Waterpark Capital of the World,” where thrill rides, lazy rivers, and indoor slides await all year round. In between, hike the scenic sandstone bluffs at Devil’s Lake State Park, cruise the Wisconsin River, or go retro at the downtown arcades, fudge shops, and classic supper clubs.
Featured vacation rental: New Buffalo Sandcastle
Dip your toes into Lake Michigan’s sandy shores, kayak the Galien River, then stroll the marina for fresh-caught seafood and local wines. New Buffalo’s boutiques and art galleries invite browsing, while nearby vineyards and breweries offer tastings with a view.
Featured vacation rental: Teddi Bear at the Villa
Stroll the Canal Walk, catch a concert at White River State Park, or explore quirky neighborhoods like Fountain Square for vintage finds and street art. The city’s foodie scene is booming, thanks to farm-to-table brunches and inventive cocktails.
Featured vacation rental: On the Lake at Castle Rock
Boat, fish, and paddleboard the tranquil shores of Castle Rock Lake. Rent a pontoon for a lazy cruise, cast a line for walleye, or hike the pine-lined trails at Buckhorn State Park. End your day with fireside s’mores and star-filled skies.
Featured vacation rental: Lazy Daze Manor
Art lovers and beachgoers mingle in this creative haven with a laid-back vibe. Browse galleries and studios, then climb the famous Mount Baldhead sand dune for panoramic lake views. Charter a sailboat or unwind at Oval Beach, consistently ranked among the Midwest’s best beaches.
Featured vacation rental: Forever Shores Retreat
Wisconsin’s second-largest lake is an outdoor playground, perfect for water sports, fishing, and wildlife spotting. Paddle through quiet coves or hit the ATV trails that wind through the forests.
Featured vacation rental: Ruby's House
Stroll the iconic South Haven pier and lighthouse, then hit the sandy beaches for swimming, volleyball, or simply soaking up the sun. This small town’s farmers’ markets overflow with local produce, while the Kal-Haven Trail beckons cyclists and hikers.
Featured vacation rental: Birchwood - Meadows Bliss
Nestled along Little Traverse Bay, Harbor Springs buzzes with boutiques, ice cream shops, and cozy cafes—perfect for a long weekend. Sail or kayak the crystal-clear waters, hike the Tunnel of Trees, or tee off on scenic golf courses.
Featured vacation rental: Lakeview Loft TC
Take a long weekend to tour the vineyards of Old Mission Peninsula, kayak the turquoise waters of Grand Traverse Bay, or sample cherry pie at a roadside stand. Explore Sleeping Bear Dunes National Lakeshore for epic hikes and breathtaking views, then unwind at a waterfront brewery downtown.
