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The best Airbnbs for weekend getaways from Chicago

Lakeside cottages, barns and a Frank Lloyd Wright house are all possibilities for your next weekend getaway from Chicago

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.

Esteemed architecture, wilderness and charm
1/11

Esteemed architecture, wilderness and charm

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. 

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Horses and room to roam
2/11

Horses and room to roam

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. 

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On the bluffs of Sheboygan's Lake Michigan
3/11

On the bluffs of Sheboygan's Lake Michigan

Two bedrooms in Sheboygan, WI, $200/night

This lakefront home is bright and airy—perfect for a quiet weekend away.

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Walk to the beach
4/11

Walk to the beach

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. 

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Overlooking Wisconsin wetlands
5/11

Overlooking Wisconsin wetlands

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.

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Sit under the stars in Michigan
6/11

Sit under the stars in Michigan

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. 

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Lakefront fun and games
7/11

Lakefront fun and games

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. 

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Beachfront cottage and private beach
8/11

Beachfront cottage and private beach

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.

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Count sheep before you sleep
9/11

Count sheep before you sleep

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.  

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Swim in a secluded glacial lake
10/11

Swim in a secluded glacial lake

Four bedrooms in Ingleside, IL, $340/night

Spread out on this four-acre property with 150 feet of lakefront and a private pier. 

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Quaint and cozy in Illinois
11/11

Quaint and cozy in Illinois

Studio in Antioch, IL, $125/night 

This small lakefront cottage has access to a private beach just steps away. 

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