By: Coop Daley By: Coop Daley | November 17, 2022 | Home & Real Estate Lifestyle
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 comfort to kick back and explore a new city.
Of course, with the option to pick and choose your environment, some Airbnbs stand above the rest with amenities and experiences offered within their walls.
We set out to see if we could find some of the most luxurious Airbnbs in major markets, and give them an inside look. Whether it be swimming pools, the ability to sleep 15, a cozy rooftop patio or just prime location, these Chicago homes turned our heads and got us excited about visiting the Windy City. Maybe they'll do the same for you.
See also: 10 of the Most Luxurious Airbnbs in Los Angeles
$637 / Listing
Crafted by an architect for his family in 2005, this expansive, 4-bedroom, 3-bathroom Printer's Row abode is one of Chicago's hottest Airbnbs. The home, located conveniently above a Starbucks, boasts a private rooftop with real grass—a rarity in the city. 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.
$4,500 / Listing
One-half Airbnb and one-half art gallery, this is one of Chicago’s most interesting properties! Featured in both Architectural Digest and Queer Eye designer Bobby Berk’s top 10 Airbnbs, this 13-bed property offers plenty of space and amenities for all. It also features a wide variety of art displayed throughout the property as a live-in exhibit, as well as an extensive vinyl collection with surround speakers. Outside, the property includes a rooftop balcony with a modern firepit and space for grilling, making it a perfect summer getaway.
$3,402 / Listing
A self-described “mini-hotel” for groups who wish to stay close to each other, the newly-renovated building features 20 queen beds and four two-bedroom apartments, all available for individual rental or combination. Located in downtown Chicago in the uprising River North neighborhood, this is a perfect launch spot for a group trip, vacation, destination wedding and more.
$3,193 / Listing
This large mansion, hosting 10 guests with five bedrooms, is chock full of amenities designed to please even the most picky of browsers. With three outdoor spaces–including one with a firepit–Sonos speakers placed throughout, a kitchen with wine fridge and multiple ovens, and a basement gymnasium with Peloton bike and NordicTrack treadmill, as well as afurnished roof and furnished rooftop garage deck. Just a few blocks away from Fulton Market, this property is a real urban oasis.
$3,000 / Listing
With four bedrooms, six-and-a-half bathrooms and three stories of opulent living, this modern home is smack in the middle of one of Chicago’s most luxurious neighborhoods with plenty to get excited about. This listing offers access to the entire home, so you can enjoy a 1,400-square foot rooftop, wide-open living spaces that can seat as many as 10 people, and a luxurious chef’s kitchen with an option to have brunches and dinners catered by a private chef. For a taste of better living, perhaps nothing has this Airbnb beat!
$2,001 / Listing
Located in scenic Old Town, this modern mansion comes full of goodies for all guests, including a sauna, steam room, two gyms with plenty of appliances, movie theater with 120-inch screen, and a large game room with golf and shuffleboard. The mansion also features two kitchens, five bedrooms and two common spaces. With the Gold Coast neighborhood just a walk away, this mansion is a real deal.
$1,842 / Listing
While it’s not necessarily a downtown darling, this 16-guest home earns notice for its wonderful living spaces and spacious backyard. The home features eight bedrooms, a chef’s kitchen with an option for privately-catered meals, and entertainment features such as a 4K TV. This is a perfect home-away-from-home to host your family or friends while taking in the Chicago scene. Be sure to enjoy the backyard and nearby farmers market!
$1,529 / Listing
Seemingly straight out of HGTV, this home could be yours for the night for just a bit more than $1,500. Its six bedrooms sleep up to 16 guests, making this getaway more of a mansion than a city stop. Enjoy a private courtyard and 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 standard with a chef’s kitchen. We can't get over that dazzling center island which allows guests to watch the cooking, and there's an outdoor fire pit for toasty drinks after dark. Located near Wrigley Field and the Zoo, this is a perfect spot for families and friends alike.
$1,234 / Listing
Ever wonder what it’s like to live in a factory for the day? No? Well, this is still a fun pick. With a 26’ timber-beamed ceiling and a space reminiscent of the International Space Station, this boat house is perfect for a wide variety of parties and events, with ample event space and a restaurant-sized kitchen to boot. If you’re looking for something beyond the event space, 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. Come make this place a factory of fun.
$1,100 / Listing
With 69 reviews rounding to a 4.97 average, this is perhaps one of the most coveted stays currently on the Chicago market. Hosting eight guests in three bedrooms, the condo comes with plenty of the standard features including an outdoor terrace, fresh towels and linens cleaned daily, maid service, a fully-stocked kitchen and bathroom, and the option to bring your pet for an additional fee. Of course, the property itself is also gorgeous, with high ceilings and fun furniture strewn about the space. Plus, it's only two minutes from downtown. It’s hard to find a better deal than this!
$1,096 / Listing
A mile from Michigan Avenue, this Wicker Park home can host up to 10 folks 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, while those who prefer to watch can chill on the rooftop deck up above which comes complete with a propane grill and seating area. Inside offers plenty of amenities as well, including a home office with standing desk, kitchen with quartz countertops, and a movie theater with popcorn machine and Playstation 5. Sounds like a college kid’s dream.
$1,056 / Listing
Built in 1897 and renovated in 2017, this grand penthouse hosts 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 television, pool table, primary bathroom with jacuzzi and steam shower, and a gorgeous wood patio overlooking the city. The property is well-reviewed, having received a 4.93 average on 116 reviews. Anyone booking this place is almost guaranteed a good time.
Photography by: Courtesy of Airbnb and hosts