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Curbed Cup 1st round: (5) Bridgeport vs. (12) Old Irving Park

Which neighborhood should advance? Cast your vote now!

The downtown skyline from Bridgeport
Flickr Creative Commons/Debbie Mercer

The Curbed Cup, our annual award for the Chicago neighborhood of the year, is kicking off with 16 areas vying for the prestigious (fake) trophy. This week we'll have two matchups per day, and all the results and the full tournament bracket will be reviewed on Friday. Voting for each pairing ends 24 hours after it begins. Let the eliminations commence!


For decades, this southwest side neighborhood had long been for being the home base of the Daley family and the Cook County political machine, but today, Bridgeport is best known for its creative community. A working class community, Bridgeporters are proud of their neighborhood and their Chicago White Sox. Popular neighborhood anchors include Maria’s Packaged Goods & Community Bar, Bridgeport Coffee House, Co-Prosperity Sphere. Bridgeport has long been a quiet, affordable community, which has attracted residents from quickly gentrifying areas on the North Side like Logan Square, Humboldt Park, and West Town.

Bridgeport made it all the way to the finals in the 2014 Curbed Cup, but was defeated by Logan Square. Will this proud South Side ‘hood make it the full distance this year?

Old Irving Park

This quiet residential neighborhood is filled with old Victorian homes and green space. For many, Old Irving Park really hits that sweet spot of convenient city living with the easy-going nature and privacy that the suburbs offer. And similar to other northwest side communities, Old Irving Park is tight-knit. The neighborhood has active community groups and residents work closely with the local schools. In our call for Curbed Cup neighborhood submissions, one reader expressed why she believed Old Irving Park deserved a spot in this year’s bracket. “Old Irving Park is having their moment right now,” the reader stated. “Between our neighborhood association, our schools, our local businesses, and our Alderman—we are all working together to make OIP great!”

But now, the decision is in your hands: Which area should advance? Cast your vote below, and may the best neighborhood win.