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These days, the trendy set is just as inclined to book a luxury vacation rental through an online service like Airbnb, VRBO or HomeAway as they are to check into a hotel. But one needn’t have a plane ticket to get away from it all. Treat yourself to a Chicago staycation at these stellar rental properties.

The 3,000-square-foot penthouse in the South Loop

The High Life
When it’s time to celebrate, it’s hard to top a penthouse. Located in River North’s Grand Plaza building, Penthouse No. 1 is a stunning three-bedroom, two-bathroom duplex on the 55th and 56th floors. Enjoy breathtaking views through 20-foot windows and a full wraparound deck. The master and guest bedrooms can be found on the second floor, while the great room, kitchen and dining areas are on the first. Building amenities such as a fitness center and indoor and outdoor pools seal the deal. From $625 per night

In the Loop
There’s nothing like enjoying a deck in the warm weather, and this 3,000-square-foot penthouse in the South Loop will help you celebrate the outdoors in rare style. Handsomely appointed with rich woods and contemporary furniture, the three-bedroom, three-bathroom penthouse features a second-floor master suite with a king-size bed and private terrace, in addition to the main terrace. Can you say summer soiree? $400-$1,000 per night

Game On!
When heading to Wrigley for the afternoon just isn’t enough, try a weekend at an Inn at Wrigley Field apartment. Recently featured on the Travel Channel, the four-bedroom units feature down bedding, a fully equipped kitchen, fireplace, dining area and in-unit washer and dryer. The real draw, of course, is catching a few Cubs games—and feasting on ballpark-style food galore—on the rooftop. Price upon request