Chicago hotels come in all shapes and styles, but why not have a truly unique experience on your next vacation or staycation in the Windy City? Below are some of the coolest and most unique Airbnb stays in Chicago including a yacht with a city view, a Tudor castle, a home designed by architect Frank Lloyd Wright and a 1904 former factory turned into a loft.  There are a lot of Airbnbs in Chicago that are fun, funky, and truly unique. Make your next trip to the Windy City truly unforgettable! 

6 Cool and Unique Airbnbs in Chicago

In a city as crazy about architecture as Chicago, why stay at a run of the mill hotel? Below find 6 of the coolest accommodation options in the city.  I am an affiliate for Stay22 and Airbnb, so I may earn a commission if you purchase through my links.

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Stay on a Yacht

Burnham Harbor yacht Airbnb

Stay on a 36-foot Beneteau sailing yacht on the dock at Burnham Harbor, next to Soldier Field. Sleeps four, and has two private staterooms. The location is steps from the Shedd Aquarium, Field Museum, Planetarium, Grant Park, Pritzker Pavilion, Buckingham Fountain, and Soldier Field. You’ll have stunning views of the cityscape and summer fireworks. 

Perk Alert: Swim off the boat in Lake Michigan.  

Boat includes central air, full bath with hot water shower, a full galley with microwave, fridge, oven, stove, gas grill, flat-screen wifi TV, high-speed WIFI.

Perfect for Chicago Bears games and concerts at FirstMerit Bank Pavilion at Northerly Island, or McCormick Place events. 

Find the boat on Airbnb

Stay in a Tudor Castle

Burton H. Hales Mansion in Chicago

This four-bedroom castle-like Revival Tudor Mansion is located in North Oak Park. The Burton H. Hales Mansion comes with cleaning and security staff.

Find the Castle on Airbnb

Stay in a Historic Rowhome 

Historic Rowhome in Chicago

Four bedroom newly renovated historic rowhome is located in the heart of Chicago’s Gold Coast’s bustle.

The Gold Coast neighborhood borders Lake Michigan and where you’ll find Oak Street Beach.  Upscale shopping and open-air restaurant dining is nearby beautiful tree-lined North Rush, North Clark, and East Oak streets. From the and city views. The best nearby sightseeing is the amazing views from Oak Street Beach and the International Museum of Surgical Science which is housed in a 1917 mansion.

Find the Rowhome on Airbnb

Stay in a Home Designed by Frank Lloyd Wright

Emil Bach House in Chicago designed by Frank Lloyd Wright

Oak Park, Illinois is home to the world’s largest collection of Frank Lloyd Wright designed buildings and houses, with 25 structures built between 1889 and 1913.

The Emil Bach House is a Prairie style house in the Rogers Park neighborhood of Chicago that was designed by Wright in 1915.

Emil Bach House is one of only a few Frank Lloyd Wright homes that you can rent as an Airbnb! This 3 bedroom home is a meticulously restored Wright original, updated with modern conveniences and comfort.

The entrance and main floor was designed by Frank Lloyd Wright to be a “journey” for guests. Like many of his homes, they are designed to be an experience from the front walkway to the “front” door and throughout the home. 

Find the Frank Lloyd Wright on Airbnb

Stay in a Penthouse

Penthouse View in Chicago

A high-end luxury three-bedroom penthouse located downtown with spectacular city view from a private roof deck. The property is stunning and designed by a famous Chicago Designer. 

The penthouse is located within walking distance or a short Uber ride to much of what you’ll want to explore in Chicago. Located 5 blocks to The Loop and Magnificent Mile/Rush Street (shopping district), 3 blocks from the bar/restaurant scene in River North, 5 blocks to Gold Coast’s Viagra Triangle (area filled with bars/restaurants), 6 blocks to Wells Street (party street filled with bars and restaurants), 10 blocks to the Beach.

Find the Penthouse on Airbnb

We hope our list of cool & unique Airbnb’s in Chicago helps create your perfect day when you visit.

Stay in a 1904 Former Factory Converted into a Loft

Former Factory Converted into a Loft

This three-bedroom loft has a screening room with a surround sound system, an industrial-chic chef’s kitchen, three spacious bathrooms, is elegantly decorated, and truly a unique accommodation. It’s a perfect location; an easy walk to cafes, restaurants. 

Find the Loft on Airbnb

Now that you have your Chicago Airbnb, check out our picks for the Best Breakfast in Chicago

Wondering what to do after breakfast? How about a Bike Ride Around Chicago? Or check out our list of the Top Things to Do in Chicago!

If you’re interested in Airbnb and have never used it before, you can use this link to save $40 on your first Airbnb booking.

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