The Curbed Cup, our annual award for the neighborhood of the year, is kicking off with 16 neighborhoods vying for the prestigious (fake) trophy. We’ll reveal each of the neighborhoods this week, and polls will be open for 24 hours so you can cast your vote as to which ones should advance. Let the eliminations commence!

(1) Woodlawn

The Curbed Cup leads off with a match between two neighborhoods that both have many changes on the horizon. Last year Woodlawn won with roaring support, will they be able to do it again?

As the home of the Obama Presidential Library, the neighborhood has received much of the spotlight. The project is expected to be a major economic boost for the area. Residents have already seen their home values rise and the area’s first new grocery store in more than 50 years will open this year.

Plans are in the works to revamp the Cottage Grove Green Line station and the much-needed Trianon Lofts, an apartment building with a 50-50 split of affordable and market-rate units, opened this year. Unlike some other areas seeing momentum, Woodlawn residents have a firm grasp on their community’s renewal.

(8) Lakeshore East

Curbed Cup’s second Elite Eight contender, Lakeshore East hit bit of a roadblock last week as the developer of three high-rises got a rejection from alderman. Although, this relatively new neighborhood has plenty more to admire.

Curbed Chicago Flickr pool/Carl Larson

The collection of skyscrapers and townhomes is a master-planned city within a city. It’s considered by many to be a triumph of the modern urban landscape.

Home to architectural icons such as Jeanne Gang’s Aqua and the skyline-altering Vista Tower, the neighborhood centers around a rectangular tract of green space featuring a playground, dog park and decorative fountains. The area is a dream for downtown commuters and is a short walk from the Loop, Maggie Daley Park, Millennium Park, the Chicago Riverwalk, and the Lakefront Trail.

It’s not your low-rise Chicago neighborhood, but that hasn’t stopped residents from embracing the density, settling down and raising families there.

The choice is yours, which neighborhood should advance in this year’s Curbed Cup? Cast your vote below!