Lake Shore Plaza is a 38-story tower in Streeterville sitting practically on top of Lake Michigan, and the amenities earn their keep: an outdoor heated pool with a Jacuzzi and a big sundeck for summer, plus a winter sauna and fitness center for the cold months, all watched over by 24-hour door staff. The units run studios through two-bedrooms with dishwashers and serious closet space, and overnight guest suites and on-site garage parking are nice bonuses. You can grab coffee at Cupitol Coffee & Eatery a couple minutes away, catch live music at Winter's Jazz Club, or take a quick walk to Bennett Park. The Whole Foods is about 7 minutes on foot, and the Grand Red Line stop is roughly a 16-minute walk when you need the train.