If you got it, flaunt it. Chicago's most fabulous properties come with custom wine cellars, private rooftop bar-lounges, and indoor and outdoor pools—all that's required to live the high life.
Rendering courtesy of Steelblue/Crescent Heights
Chicago’s tallest residential rental tower rises along Grant Park, so you know the views are spectacular. Only 126 of the Rafael Viñolydesigned skyscraper’s 800 units make up the Skyline Collection: two- to four-bedroom homes from floors 49 to 76, each with access to an entire 70,000-square-foot floor of amenities that include a golf simulator and a Pilates studio, plus a private bar with dramatic fire pits and outdoor lounge space for the ultimate in entertaining. $4,000-$25,000 per month
Photo by Positive Image Photography/Courtesy of @Properties
One of the largest estates in Chicagoland clocks in at 17,000 square feet, surrounded by 26 acres of healing gardens, a meditation deck, a rock fountain, walking paths and some 1,000 mature trees designed by landscape architect Hoichi Kurisu. The pièce de résistance of St. Charles’ Woodgate Estate is not the outdoor pool but the indoor saltwater one, enclosed in 66 by 28 feet of glass and, yes, with a hot tub attached. When you’re not using the theater or the spa, practice your backhand on the tennis court or host a full-fledged yoga retreat with lectures held in the conference room—which every proper estate needs, natch. $2.4999 million
Photo by Chicago Home Photos/Courtesy of Berkshire Hathaway Homeservices KoenigRubloff Realty Group
The 15-foot-tall floor-to-ceiling windows of Unit 950 may drench the spacious loft at 900 N. Kingsbury (aka Domain), but all that soothing sunshine can’t penetrate the custom wood-lined cellar ready to store a king’s army’s worth of vintages and its requisite stemware. The building is outfitted with a gym and a roof deck (plus three parking spaces for this owner), so you can share that 2012 Chateau Lafitte with the neighbors, or enjoy it in private from one of the 5,500-square-foot condo’s three decks. $3 million, klopasstratton.com
Photo by Jonathan Allen/courtesy of One Bennett Park
Creating its own micro-hood within Streeterville, One Bennett Park offers renters and owners alike a new 1.7-acre green space by Michael Van Valkenburgh, amenity spaces that include an entertainment suite with a catering kitchen and play rooms for children of varying ages, a 7,000-square-foot fitness center, and a 10,000-square-foot outdoor recreational deck with cabanas, fire pits, reservable outdoor kitchens and a pool. (There’s also a dog run and lawn bowling!) Floors 41 through 66 are reserved for owners, who gain exclusive access to a 5,000-square-foot club-lounge whose main attraction is a killer billiards room that overlooks Lake Michigan. From $2 million
Photo by Michael Robinson/courtesy of Morgante Wilson
Hello, gorgeous! What kids wouldn’t want to run up and down these spiral stairs to their bedroom, all the while illuminated by the skylight above? Designed for a family with small children, this new-construction single-family takes inspiration from David Adler but with slightly more grace: Maple-and-mahogany inlaid stairs swirl around sculptural metal balusters, all lending the home an elegant sophistication. Should those children make it all the way to the top-level fourth floor, they’re met by a wet bar, billiards area and home theater—plus stunning views of the city. The basement is strictly adults-only: The wine vault and tasting room feature a barrel-vaulted brick ceiling that makes the space feel more secret grotto than big-city cellar. Not for sale
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