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The 9 coolest Airbnb rentals in Chicago

Looking for a 'staycation' in Chicago? Visiting our city? Book one of these Airbnb rentals for a cool alternative to a hotel

Over the past few years, Airbnb has changed the way we vacation. The accommodation booking website provides a much more personalized experience than downtown hotels, and often at a reduced rate. The network gives you the opportunity to board up in a stranger's apartment—which is probably nicer than your own.

From a converted church to an entire house, there is no shortage of groovy pads that you can rent out for your own staycation or visit to Chicago. Here are the coolest Airbnb rentals we found online, from the the Loop to Hyde Park and beyond.

For a great list of Chicago hotels, click here

RECOMMENDED: Our guide to weekend getaways from Chicago

 

1/9

One-bedroom in Bucktown, $115/night


The one that's on the river

The Chicago River might stink, but this apartment does not. The excellent view might make you forget about all of the waste that has been dumped into the waterway over the years.

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2/9

One-bedroom in Wicker Park, $200/night


The one that's good enough for God

Whether you are a devout Christian or actively trying to be as blasphemous as possible, this converted century-old church is a lovely option. The stained-glass windows and divine woodwork could have you saying "Amen" by the end of your stay.

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3/9

Six-bedroom Gold Coast mansion, $1,255/night


The one that was owned by a shoe tycoon

The Florsheim Mansion was built by architect Andrew Rebori in 1938. In 1946, it was sold to Lillian Florsheim, a shoe heiress and renowned sculptor. It was later renovated by Florsheim's son-in-law Bertrand Goldberg, who was the architect behind Marina City and the Prentice Women's Hospital Building.

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4/9

Four-bedroom in Wicker Park, $1,250/night


The one that epitomizes Wicker Park's gentrification

Wicker Park has become a ritzy neighborhood over the past 15 years, as this pad perfectly exemplifies. You'll have to fork over a $1,000 security deposit for your stay, but that's the price you pay for easy access to those fantastic shops and restaurants on Milwaukee Avenue. 

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5/9

Two-bedroom in Bronzeville, $495/night


The one that's literally a boat

Owning a boat in Chicago is pretty impractical, but living on one for a couple of nights actually sounds pretty cool. This 54-foot yacht is docked at 31st Street Harbor, which sounds like a terrible experience in the winter (and a dream in the summer).

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6/9

One-bedroom loft in Lakeview, $129/night


The one that's the loft of your dreams

Movies and television shows would have you think that there are a lot more lofts in big cities than there actually are. There's plenty of room for activities in this stylish pad.

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7/9

Two-bedroom in Hyde Park, $150/night


The one with the view you can't afford

Hyde Park's Promontory Point offers one of the best views in the entire city. The views from this place, which is located across Lake Shore Drive from the point, might be even better.

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8/9

Two-bedroom in Andersonville, $199/night


The one that'll make you feel like you have your life together

A night's stay in this one-bedroom North Side pad will make you forget that you still don't know how to write a check. A fireplace, breakfast bar and a great rooftop deck will do that, though. 

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9/9

Three-bedroom in Lakeview, $499/night


The one that's just far enough away from Wrigley Field

Even the Palace of Versailles would lose its charm if it were adjacent to Wrigley. Luckily, this place is tucked away on nearby Halsted Street and has a rooftop view of the stadium (as well as a hot tub).

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