When it comes to vacations and getaways, no app is more popular than Airbnb. The home-sharing service has become a top destination for tourists and travelers, as owner-hosted homes and apartments offer a worthy alternative to the traditional hotel room, giving guests ample space and the opportunity to explore a new city.
Of course, with the option to pick and choose your environment, some Airbnbs stand above the rest with the amenities and experiences offered within their walls.
We set out to see if we could find some of the most luxurious Airbnbs in the Windy City and gave them an inside look. From swimming pools, cozy rooftop patios and prime locations, these Chicago homes turned our heads and got us excited about booking our next staycation. Let’s see if they’ll do the same for you.
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From $725 / Listing
Crafted by an architect for his family in 2005, this expansive, four-bedroom, three-bathroom Printer’s Row abode is one of Chicago’s hottest Airbnbs. The home boasts a private rooftop with real grass—a rarity in the city—a living room, dining room, a primary bedroom and the capacity to house eight guests. This urban oasis has been featured in magazines and TV commercials, so snag it if you can, to see what all the hype is about.
From $4,500 / Listing
Featured in both Architectural Digest and Queer Eye designer Bobby Berk’s top 10 Airbnbs, this nine-bedroom, three-story home offers up ample space and amenities. One-half Airbnb and one-half art gallery, it encompaaes a wide variety of art displayed throughout as a live-in exhibit and an extensive vinyl collection with surround speakers. Outside, the property has eleven rooftop balconies, including a rooftop terrace with a modern fire pit and space for grilling.
From 1,070 / Listing
This 6,200-square-foot home can hold up to 12 guests and touts amenities for visitors of all ages, including a rooftop patio with lounge seating, a sauna, a steam room and a game hall with shuffleboard and golf arcade games. Located just a short trip away from North Avenue Beach, Lincoln Park Zoo and the Mag Mile, the home features a spacious kitchen with a Sub Zero refrigerator, comfy couches, flat-screen TVs, two indoor fireplaces and a private gym with Peloton, exercise equipment and weights. Guests can also opt to work from this staycation spot with a workspace, a desk and a coffee bar.
From $1,650 / Listing
This large mansion, hosting up to 10 guests with five bedrooms, is chocked-full of amenities designed to please even the most picky of browsers. Situated just a few blocks away from Fulton Market, with three outdoor spaces—including one with a fire pit and Sonos speakers placed throughout—a designer chef’s kitchen, a furnished roof, a rooftop garage deck, a fully-equipped basement gymnasium and more, guests will have everything they need to enjoy their stay.
From $900 / Listing
Overlooking the skyline, this ultra-high-end apartment can host up to 16 guests and features a private terrace, complimentary parking, a 24-hour doorman and floor-to-ceiling windows. Visitors can make themselves at home in the loft’s sprawling open living room, dining room and chef’s kitchen, with gas-powered Gaggenau ranges, a Gaggenau oven and microwave, a restaurant-sized refrigerator and freezer, dishware, cutlery and state-of-the-art kitchen appliances, including a coffee maker. With three bedrooms, three bathrooms and eight beds, the home is ideal for hosting family gatherings, extended stays and luxe staycations.
From $1,279 / Listing
This 16-guest home earns notice for its sunlight-drenched living spaces and spacious backyard. The residence features eight bedrooms, a chef’s kitchen with an option for privately catered meals and entertainment features such as five 4K flat-screen HD TVs, streaming services, WiFi and more. This is an ideal home-away-from-home to host your family or friends while taking in the Chicago scene. Be sure to enjoy the backyard and visit the nearby farmer’s market.
From $572 / Listing
Built in 1908, this Tudor Revival-style home has undergone a fully-customized renovation that brought in state-of-the-art appliances, design features and luxe amenities. The historic Manor House, nestled in Ravenswood Manor, encompasses three floors of living space, three primary suites, five beds, 3 ½ baths, a dining room, a chef’s kitchen, a workout area, a custom stone and glass wine cellar with more than 30 wine options and a granite and stone bar that seats up to four. Upon request, visitors can receive a private chef and a bartender for all their entertaining needs.
From $1,129 / Listing
Seemingly straight out of HGTV, this six-bedroom home sleeps up to 16 guests, making this getaway more of a mansion than a city stop. Enjoy a private courtyard, a backyard and a private balcony on each level that will give every guest their own skyline view. As is typical for this list, the home comes with a chef’s kitchen. We can’t get over the dazzling center island and the outdoor fire pit for enjoying toasty drinks after dark. Located near Wrigley Field and Lincoln Park Zoo, this is a perfect spot for families and friends alike.
From $900 / Listing
What could be better than two penthouses for the price of one? This offering provides access to two penthouses on the same floor and building in River West, with access to a private balcony. Each penthouse features three bedrooms, 3 ½ bathrooms, a kitchen, a living room and a dining room. Not to mention, in the building, guests will find a 24-hour gym and yoga studio, an outdoor pool and hot tub, a gallery café, a party room with a commercial demonstration kitchen, a co-working lounge and more.
From $964 / Listing
With a 26-foot timber-beamed ceiling and design elements reminiscent of the International Space Station, this former factory-turned-luxury home is perfect for hosting parties and events, with ample event space and a restaurant-sized kitchen to boot. Aside from the sprawling, innovative layout, there’s a jacuzzi and rain shower in the primary bath, a rooftop patio and bar and plenty of beds for all 20 of your closest friends.
From $249 / Listing
Hosting eight guests in three bedrooms, this freshly renovated condo comes with plenty of features, including an outdoor terrace, a patio with a fire pit, fresh towels and linens cleaned daily, maid service, a fully-stocked kitchen, 2 ½ bathrooms and the option to bring your pet for an additional fee. Of course, the property is also gorgeous, with floor-to-ceiling windows, high ceilings and fun furniture strewn about the space. Plus, it's only two minutes from downtown.
From $1,152 / Listing
Located only one mile from Michigan Avenue, this Wicker Park home can host up to 10 guests in five bedrooms while offering some of the best outdoor spaces on this list. Guests can get their Michael Jordan on out back with a custom-built basketball court, or watch all the action from a rooftop deck up above, complete with a propane grill and seating area. Inside offers plenty of amenities as well, including a home office with a standing desk, a kitchen with quartz countertops and a movie theater with a popcorn machine and more.
From $554 / Listing
Built in 1897 and renovated in 2017, this 4,000-square-foot grand penthouse houses 16 guests, making it a perfect stay to host a large reunion with friends or family. Comprising two units connected by a private staircase, the penthouse offers plenty of fun features to pass the time, including a television, a pool table, a primary bathroom with a jacuzzi and a steam shower and a gorgeous wood patio overlooking the city.
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Photography by: Courtesy of Airbnb and hosts
