220 E Illinois Street, 1505 Chicago, IL 60611

Not every urban neighborhood has its own Ferris wheel, but then not every neighborhood is Streeterville. Just across the Chicago River from the Loop proper, it’s the home of Navy Pier and countless high-rises (historic and new, but all luxury), and it’s bustling with foot traffic from locals and tourists. That vibrancy fuels a great restaurant and bar scene, some of the city’s best retail, and a host of cultural and recreational attractions. Streeterville juts out into Lake Michigan north of the mouth of the Chicago River, and so many of the buildings offer incredible views. Where it isn’t bounded by water, it’s bounded by the Magnificent Mile, and thereby defines Chicago upscale. This area is full of historic landmarks and is pincushioned by some of the city’s tallest skyscrapers — and quite a few taller ones are planned along the southern waterfront. Transportation to the rest of Chicago is direct via Lakeshore, the L, or bus, though walking is a pleasure — as are rides in the water taxis when the weather is warm.