We know you can find some of the coolest Airbnb rentals in Chicago, but living in the Midwest also means we’re surrounded by some phenomenal long weekend opportunities, including stellar Airbnb options in Michigan, Wisconsin and elsewhere in Illinois. The next time you sit down to plan a weekend getaway from Chicago instead of a day trip, check out this list for some of the coolest Airbnb rentals we found online. Just remember: Always do your research and check for reviews, availability and pricing before booking.
Four-bedroom Frank Lloyd Wright house in Two Rivers, WI, $425/night
Who wouldn’t want to spend the night in a Frank Lloyd Wright house? The Bernard Schwartz House (1939) is set near a marsh and, besides its architectural wonders, is the perfect jumping off point for anyone who fancies fishing, considering its location in Two Rivers.
Barn in Kenosha, WI, $126/night
You won't forget an overnight stay in this 1910 barn on more than five acres between Chicago and Milwaukee.
Two bedrooms in Sheboygan, WI, $200/night
This lakefront home is bright and airy—perfect for a quiet weekend away.
Two bedrooms in Union Pier, MI, $255/night
Fire up the grill, but be sure to wait 30 minutes before swimming in the heated pool. This place has tons of amenities.
Two bedrooms in Mukwonago, WI, $200/night
Approximately 20 minutes away from Lake Geneva, this lake house looks over the Natural Conservancy Wetland, and you'll have easy access to the water, plus a pier, cabana and canoe.
Three bedrooms in Bridgman, MI, $390/night
Hang out around the fire or hop in the hot tub at this two-acre property close to New Buffalo.
Three bedrooms in Genoa City, WI, $300/night
Besides a relaxing hot tub and a view of the lake, guests can also kick back with pool, darts and drinks at the bar in the basement.
One bedroom in Coloma, MI, $325/night
Miles of beach are at your feet at this 1950s cottage, located in a private area near wooded dunes.
Loft in Helenville, WI, $90/night
Get away without having to travel too far when you climb up into this rustic loft between Madison and Milwaukee. Plan ahead and rent kayaks or bicycles, too.
Four bedrooms in Ingleside, IL, $340/night
Spread out on this four-acre property with 150 feet of lakefront and a private pier.
Studio in Antioch, IL, $125/night
This small lakefront cottage has access to a private beach just steps away.
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