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Curbed Cup 1st round: (1) Woodlawn vs. (16) Bowmanville

Which neighborhood should advance? Cast your vote now!

Aerial view of Jackson Park on a sunny day in Chicago.
Jackson Park
Curbed Chicago Flickr pool/Eric Allix Rogers

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

Last year Woodlawn took home the Curbed Cup after a strong run, and this year they have proven that they’re still a worthy contender. The Obama Presidential Library caught more national attention when renderings for the project were released earlier in the year. The Tod Williams and Billie Tsien designed project is expected to generate a multi-billion dollar impact and create more than 2,500 jobs, according to reports this year. However, the project has not escaped scrutiny for what advocacy and watch dog groups see as a lack of transparency from the organizers.

While construction hasn’t started yet on the massive development, residents have already seen an impact. Neighborhood home values have risen and the area’s first new grocery store in more than 50 years will open on the corner of 61st Street and Cottage Grove. 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.

These are all indicators of significant growth that keep the long-term residents in mind. Unlike some other areas seeing momentum, Woodlawn residents have a firm grasp on their community’s renewal and have taken a community-oriented approach to development.


(16) Bowmanville

It’s likely that you’ve never heard of Bowmanville, and might even doubt it is one of Chicago’s actual neighborhoods. You’ll find the small but mighty neighborhood tucked between Andersonville, Ravenswood and Rosehill Cemetery. A reader nomination made a fierce case for this community helping it earn a 16-seed spot.

We learned earlier this year residents banded together to raise over $50,000 to save their community garden from the threat of possible future development. With the land secured, community organizations are planning to double the green space at Gateway Garden and create a year-round vegetable garden for the public.

Perfect night at @halfacrebeer Balmoral Tap Room ✨

A post shared by @morethandeepdish on

The mostly residential neighborhood is sprinkled with block parties, yard sales and an annual Garden Walk where neighbors open up their backyards to visitors. Considering its size, we were impressed to find within its borders a Michelin-approved Korean barbeque restaurant San Soo Gab San and a budding beer scene. Half Acre opened up a new taproom, kitchen and beer garden at its brewing facility there and Spiteful Brewing has plans to move in next door.

One of our reader nominations admitted not a lot of people know his neighborhood but, “...it’s a wonderful corner of our city, and people who move here swear they’ll never leave!”

Now the choice is yours. Which neighborhood will be lucky enough to advance? Cast your vote below!