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Curbed Cup 1st round: (7) Uptown vs. (10) Lakeview

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Which neighborhood will move ahead? Vote now!

Aragon Ballroom in Chicago’s Uptown neighborhood
Keith Cooper / Flickr

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!

(7) Uptown

Uptown is a neighborhood that is a perfect union of old and new. The area is dotted with architectural gems including the Moorish-style Aragon Ballroom, the legendary 100-year-old Green Mill Cocktail Lounge, and even an Art Deco Post Office. In past Curbed Cups, Uptown was the reigning champ in both 2010 and 2011—so will they do it again this year?

Aragon is just one of many theaters and entertainment venues in Uptown. There’s also the gorgeous Riviera Theater and the movie palace Uptown Theater, which is in desperate need of restoration. A mini pagoda set atop the Argyle el station is a nod to the many Chinese and Southeast Asian restaurants that pack the street. The area also has little shops with knick knacks and vintage items that line Clark Street.

The neighborhood claims Montrose Beach and The Dock—both popular summertime destinations. The Montrose Point Bird Sanctuary is a unique public space, that provides a scenic rest stop for birds migrating in fall or spring.

In more recent news, Uptown’s historic Agudas Achim Synagogue is being creatively redeveloped into apartments and a handful of TOD projects will bring additional residences to the area. This year the $203 million Wilson stop restoration was completed after nearly three years, signaling an important step in the neighborhood’s restoration.

(10) Lakeview

Lakeview is no doubt one of Chicago’s busiest neighborhoods. The activity never stops between Boystown, Wrigleyville, the clusters of college kids and young families.

Even with a few roommates, finding a decent, reasonably priced apartment is difficult. But the sacrifices made in personal space allow for proximity to Wrigley Field, the bustling restaurant and bar scene, quirky shops on Halsted and Clark streets, great comedy and music venues and a good slice of the Lakefront Trail.

Wrigleyville has been in a massive transition since the Cubs’ 2016 World Series victory. The number of dive bars are dwindling and, for some reason, the demolition of the neighborhood McDonald’s and Taco Bell, caused an outcry from residents who held fond memories there. The Park at Wrigley was completed this year and now hosts farmer’s markets, family neighborhood events, and offers trendy restaurants and bars for Cubs fans. Construction on Hotel Zachary across the street and the Addison-Clark retail and apartment project are slated to open in 2018.

The transformation of Wrigleyville is leading Lakeview away from its rough-around-the-edges past into a new era. At least two new Targets and a massive Whole Foods have opened and brand new multifamily projects are popping up all over the area.