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Curbed Cup Final Four: (1) Woodlawn vs. (4) Logan Square

Which neighborhood should advance to the Finals? Vote now!

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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 Final Four pairs two neighborhoods with strong communities and lots of ongoing development. Last year, it was Woodlawn that snagged the trophy, but will they be able to for a second time?

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 and provide thousands of jobs. 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. A strong community voice is an admirable quality, especially when so many major developments are changing the area.

(4) Logan Square

Over on the Northwest Side we’ve got Logan Square. People are flocking to this neighborhood for beautiful boulevards, modest rent, tucked-away pubs, crafted cocktails and burgeoning restaurant scene. Bon Appetit named Chicago as Restaurant City of the Year thanks to several neighborhood favorites including Giant, Fat Rice, Mi Tocaya Anotjeria, and Lula Cafe.

Developers have rushed to throw up new, luxury apartments alongside the neighborhood’s bungalows and greystones. Although the city’s expanded TOD incentives did result in a lot of new development along Milwaukee Avenue, not all have been expensive housing.

Earlier in November an LGBTQ-friendly affordable housing project was cleared to rise and residents have been vocal about ensuring development be community driven too.

Now, the choice is up to you. Should Logan Square make it to the Finals? Or will Woodlawn climb to the top again? Cast your vote now!