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Fun & Relaxing Group-Friendly Airbnbs Outside Chicago Worth Planning a Trip Around

Whether you're looking to escape for a weekend or a week, these are some standout Airbnbs worth keeping on your radar for you and your crew.

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Group getaways outside the city are great, as long as you manage to line up two essential components: a well-curated crew of people without any wet blankets, and a spacious and relaxing place to call home wherever you're going. Unfortunately, we can't offer much help figuring out the former (that's on you), but we can offer some guidance on the latter. In fact, we did a little digging to find some spectacular group-friendly Airbnbs in laid back locales in Michigan, Wisconsin, and rural Illinois that are worth planning an entire getaway around. And even better? They're all under three hours from the city by car. 

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Saugatuck Oasis With a Heated Pool

Saugatuck, Michigan
8 guests, $766 per night

Distance from Chicago: ~2.5 hours
Set on a green 1.5 acres, this charming and spacious lodge-lie home is decked out to serve as the ultimate escape no matter what time of year you're there. During the warmer months, the professionally landscaped yard is a great place to lounge thanks to its screened in porch, heated pool, outdoor shower, and basketball court. Indoors, meanwhile, it features a grand living room with vaulted ceilings (and a towering stone fireplace), plus a gorgeous pro-grade kitchen and huge dining area. Also, it's just a short walk to enjoy stunning views of the nearby Kalamazoo river byways. 

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Turkey Run Cabin

Wisconsin Dells, Wisconsin
16+ guests, $531 per night 
Distance from Chicago:
~3 hours
Desperate for some true country living? This spot delivers. It's tucked away and surrounded by lush greenery and wildlife, which you'll be able to easily keep an eye on from either the extra wide front deck, oversized back deck BBQ area, or backyard fire pit. Inside, you'll find plenty of areas to decamp to, whether it's the huge main living room with soaring ceilings, the bar area, the second lofted living room/TV area, or in the basement where there's a full billiards room complete with its own cozy lounge nook and its own vending machine.

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The Calming Cottage

Holland, Michigan
12 guests, $350 per night
Distance from Chicago:
~2.5 hours
Set in an idyllic wooded are, "cottage" undersells this home just a bit considering it's essentially a picture perfect minimalist West Elm floor display come to life and surrounded by nature. Even though it's just minutes to all the action in Holland, you and your crew will likely be content staying put to just soak up the relaxing vibes from the huge couch in the sun-soaked family room, hang out in the open concept kitchen cooking meals, or chill out on the huge front porch or back deck. 

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A 4-Story Estate on Lake Geneva

Lake Geneva, Wisconsin
10 guests, $2,900 per night
Distance from Chicago:
~1.5 hours
While this place is admittedly on the pricey side, it's a remarkable waterfront home that you'll never forget. The modern four-story house is stacked with enormous windows looking out onto an incredible view of Lake Geneva (the sunset from its perch are truly insane). You'll also get access to all of its outdoor amenities including the lakeview pool, private pier, and a spacious deck with not one but two BBQ grills. Inside, it's a true vacation paradise of amenities with an epic kitchen, sprawling dining table for 14, three fireplaces, billiards, fitness room, an arcade, and a sauna. 

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Private Retreat on Piskatee Bay

Johnsburg, Illinois
12 guests, $1,000 per night
Distance from Chicago:
~1.5 hours
Feel like giving lakefront living a test-drive? You'll get just that at this vacation dream house, which boasts 6,000 square feet of living space across four levels -- and most importantly, incredible panoramic views of Chain O' Lakes. It also uniquely blends indoor and outdoor living thanks to a huge windowed "lake room" off the back that opens up onto a large patio, which continues straight down to the lakefront. Other perks include a chef's kitchen, several entertaining spaces, two fireplaces, parking for 10 cars, and a ping pong room.

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Modern Getaway with a Backyard Pool Lounge

Douglas, Michigan
10 guests, $1,098 per night
Distance from Chicago:
~2.5 hours
This modern farmhouse is the ultimate warm weather escape, particularly out back where there's a huge, brand new heated saltwater pool (which is open May-October) and a standalone modern pool house complete with a glass garage door, fireplace, flatscreen TV, bar/lounge area, and an outdoor shower. The main house, meanwhile, boasts a super relaxing screened in porch, a huge kitchen, a living room on the main floor, a basement lounge, and five bedrooms, making it perfect for a larger vacation crew.

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The Green Oasis

Fennville, Michigan
10 guests, $400 per night
Distance from Chicago:
~2.5 hours
Just a quick drive to downtown Saugatuck, this relaxing mid-century respite sits on a lush 3.5 acres with a meticulously landscaped yard and garden. Out back, there's a gorgeous in-ground pool with a canopied lounge area to spare yourself the glare of the sun, plus a fire pit area to kick back with some drinks after dark and stare up at the stars. Indoors, it's furnished to the hilt with stunning mid-century touches, and is decked out with enough bedrooms and sitting areas to feel spacious even if you're rolling deep.

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Starved Rock Country Estate

Peru, Illinois
16+ guests, $685 per night
Distance from Chicago:
~2 hours
If you've always wanted to decamp to the area of Starved Rock State Park for a long weekend, you'll want to keep this 160-year old Greek Revival-style estate on your favorites list. The 4,700 square foot home itself is filled with unique original historical details (e.g., ornate horse hair and plaster molded original ceilings), plus modern amenities that bridge the old with the new (e.g., a home theater, gym, and a billiards/game room). If you happen to stay in the warmer months, the backyard is also set up for lounging with fenced in in-ground pool, lighted gazebo, fire pit, and patio.

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