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This penthouse duplex up has two bedrooms downstairs, then a massive lofted second level upstairs, which you can use as a third bedroom, a family room, a home office, whatever fits your life. The living room is the standout. Double-height ceilings, a wood-burning fireplace, and a private balcony looking out over the treeline. The kitchen's big enough to actually cook and eat in, and it opens right onto a deck for outdoor grilling and al fresco dinning. Then there's the roof deck upstairs, one of three separate outdoor spaces in this unit. That's genuinely hard to find in Wicker Park. In-unit laundry and parking are included in rent, too. Location is hard to beat: walk to some of the best restaurants and coffee in Wicker Park, the 606 Trail, the Blue Line, quick expressway access, and four bus lines.