Haute Top 5: Swanky Chicago AirBnBs For Your Windy City Stay

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Planning a getaway to Chicago (or hosting out-of-town guests?) Forgo the hotel and live like a local with one of these swanky Chicago AirBnBs instead.

1 5 Bedroom House Near Wrigley Field

Coming to town for a Cubs game? Post up with your team in this luxurious five bedroom home in the city's picturesque Southport neighborhood, walking distance to Wrigley Field. The house was completely remodeled in 2014 and features a gourmet kitchen, a theater room, steam showers, an expansive backyard with patio, and more.

2 5 Bedroom Downtown Penthouse

The listing for this building touts it as the preferred Chicago rental of AirBnB CEO and co-founded Brian Cheskyan, as well as an "Instagram Gem" and it's not hard to see why. The well-appointed space (which is actually two units in a single building) is a study in style, with exposed brick, midcentury furnishings, and a deck that boasts 360 degree views of the city skyline.

3 Converted Factory Penthouse in West Town

For $5,000 a night you and seven of your closet friends can call this chic penthouse home. The high-end amenities make the spurge well worth it: the state-of-the-art kitchen features Miele cabinetry and Sub Zero appliances, the master bedroom is framed in floor-to-ceiling windows, while the master bath offers a frameless shower and tub with a view, and the oversized roofdeck has three separate seating areas and unobstructed views of the skyline.

4 Single-Family House in Wicker Park

This stunning modern home sits in the center of one of Chicago's hippest neighborhoods, Wicker Park. The contemporary five bedroom space is filled with posh features like a cusomt chef's kitchen, open fireplaces, glass walls, and an outdoor entertaining area with a fire pit, grill, and hot tub.

5 Party-Perfect Pad in Bucktown

The word "home" drastically undersells this space, which is one of the most unique AirBnB properties listed in Chicago. The expansive loft space can be rented for both commercial or personal use and is an ideal spot for hosting a party thanks to a custom-designed bar area, wide-open floorplan, integrated sound system, and permanent disco ball.
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