Historic mansion in Gold Coast
Chicago is famous for its mansions, and you can get up close and personal with one of the most historic, thanks to this Airbnb. The Florsheim Mansion, which dates back to 1938, was originally the home of shoe heiress and sculptor Lillian Florsheim. The building features five bedrooms, five bathrooms, two living rooms and a large outdoor garden. Chicago Magazine even described it as one of the “sexiest homes in Chicago.”
Cost per night: $450
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Rooftop decks with hot tub near Wrigley
The undoubted jewels in the crown of this luxurious three-bedroom house are its rooftop decks. If the season is right, then fire up the grill and relax in the hot tub with 360-degree views of the city, including the lake, the Loop and River North skyline, and the iconic Wrigley Field. You won’t want to leave the house, but if you do, then you’re in the heart of Boystown, a lively and upscale neighborhood.
Cost per night: $399
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Artist loft with sauna in West Town
Beautifully minimal and tastefully appointed, it’s no surprise that this perfect loft belongs to an artist. Even the photos of it are stunning. What is a wonderful surprise, however, is the addition of a ridiculously great bathroom, featuring a tub made for two, a rainfall shower, and a sauna. And that’s all before you’ve even made it to the rooftop deck or checked out the great surrounding neighborhoods. As private rooms go, there can’t be many others that are this incredible.
Cost per night: $150
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High-end home in Wicker Park
For a family or group of friends looking to enjoy one of Chicago’s most popular neighborhoods, this house is ideal. It sleeps six to eight across five beautiful bedrooms and also features chic dining areas and a high-end kitchen. Outside, there are two levels of decks, with a hot tub and firepit perfect for warm summer nights. It’s also well situated for exploring Division, Damen, and Milwaukee, the main thoroughfares of Wicker Park.
Cost per night: $1,500
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Amazing yacht with lake trip included
Ever wanted to own a yacht? Now you can feel like you do, if only for a day at a time. This 49-foot vessel is the epitome of luxury, and for the price, you will get a four-hour jaunt out onto beautiful Lake Michigan, complete with captain and crew, of course, before a night docked at Northerly Island. If your budget is big and you have 15 friends to contribute, then what an experience.
Cost per night: $5,000
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“Rock N’ Roll” Airbnb in River North
This gorgeous apartment has high ceilings, hardwood floors, and a beautiful four-poster bed. But what sets it apart is its rock n’ roll spirit, with artwork, posters, and guitars lining the walls, and a record player to fill the space with music. It’s also awesomely located, above a French bistro and near other restaurants and bars, and just blocks away from the Magnificent Mile’s famous shopping options.
Cost per night: $279
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Deluxe apartment in the sky
What better way to see Chicago than by staying in a skyscraper in the Loop? This apartment sits in a 60-story building in the heart of downtown, right near the Chicago River and many of the top tourist spots. As expected, it’s a plush and classy space with beautiful furnishings and large windows, and to top it off, the building also has a swimming pool and rooftop area with even more amazing views of the city.
Cost per night: $170
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Cozy coach house in Pilsen
If you’re looking to explore Chicago’s vibrant Pilsen neighborhood, this renovated coach house is a perfectly compact and centrally located option. This light and comfy apartment is near many of 18th Street’s attractions, such as the Thalia Hall concert venue, high-end restaurant Dusek’s Board & Beer, and Cafe Jumping Bean. The chance to enjoy the cuisine and murals of Chicago’s Mexican community is also a must.
Cost per night: $125
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Artist’s loft on the 606
This Airbnb is another beautifully decorated artist’s loft, but this time located on the 606 trail, an urban park along an old elevated train line. The space has two queen beds and a spacious living space with a fully stocked kitchen and dining area. Its skylight and large windows fill the apartment with light and allow you to look out on the trail, which also easily connects you to Bucktown, Wicker Park, and Logan Square.
Cost per night: $125
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