Bridgeport

The vibe

Bridgeport is the South Side neighborhood that gave Chicago a bunch of its mayors, its classic corner-tavern culture and a tough reputation. It's changing, slowly, with artists, younger families and new spots moving in alongside the bungalows, brick two-flats and neighborhood bars that have been there forever. It's one of the most interesting places in the city right now.

The Orange Line stops at Halsted, and the Red Line stops at Sox-35th on the east side. Chinatown is right next door.

Best munchies

Kimski is inside Maria's Packaged Goods & Community Bar on 31st Street, and it does Korean-Polish food that sounds like a joke and eats like a revelation. Maria's itself is a great bar with a package goods store attached. The Ramova Grill on Halsted is a restored classic diner next to the theater.

Chinatown is a short walk east for dumplings, Sichuan and dim sum. See the Chicago munchies guide.

Things to do baked

Palmisano Park is a former stone quarry turned into a park, with a pond at the bottom, wetland paths and a hill with skyline views at the top. It's a strange, beautiful place and a great walk high. Then wander to Chinatown and Ping Tom Memorial Park on the river.

Movies and music

The Ramova Theatre on Halsted, an old 1920s movie palace, has been restored and reopened as a music venue, and it's a great room to see a show in. The neighborhood's corner bars sometimes have live music. Downtown's theaters are a short Orange Line ride north. See the movie theaters guide.

Best lake or park spot

Palmisano Park is the one. For the river, Ping Tom Memorial Park in Chinatown has skyline views and boats. The lakefront is a ride east.

A perfect baked day in Bridgeport

Start with coffee at a Bridgeport cafe, then walk to Palmisano Park. Wander down into the old quarry, along the wetland paths and up the hill for the skyline view. Have lunch at the restored diner on Halsted. Spend the afternoon walking the neighborhood, looking at the old brick two-flats and the corner taverns that have been there for generations. Head east to Chinatown in the late afternoon for dumplings and a walk through Ping Tom Memorial Park along the river. Come back for dinner at Kimski inside Maria's, then check what's on at the Ramova.

Bridgeport is a neighborhood in the middle of a slow change, and that's part of the fun: old-school bars next to new restaurants, longtime families next to artists. Be a good guest.

Getting there and getting around

The Orange Line's Halsted and Ashland stops cover the west side of the neighborhood, and the Red Line's Sox-35th stop covers the east. The Red runs all night, the Orange doesn't. The Halsted and 35th Street buses fill in the rest, and Chinatown's Cermak-Chinatown Red Line stop is a short walk northeast.

Sesh notes for Bridgeport

Bridgeport's best quality is that it doesn't try very hard. The bars are bars, the diner is a diner, the park is a quarry. Nobody's putting on a show, and that makes it one of the most relaxing neighborhoods in the city to wander high. Pick a corner tavern with the game on and the lights low, order something simple, and let the afternoon go. Then walk it off on the hill at Palmisano.

Bridgeport is classic South Side housing: brick bungalows, two-flats, workers' cottages and corner buildings with apartments over storefronts. Lots of longtime neighbors and families, so keep the sesh private and the noise low. Palmisano Park and the river parks are public, so they're for after. In summer, the neighborhood's corner taverns and back yards are where it's at. In winter, the Ramova and the diner keep things warm.

Bridgeport is also one of the better neighborhoods for a low-key day out high: not crowded, not expensive, and full of strange little surprises like a quarry park and a Korean kitchen inside a liquor store.

The good and the annoying

Next door

The neighborhoods that border this one, or are one quick ride away.

Before you go, read the Chicago munchies guide, things to do high in Chicago, best late night food in Chicago, hosting a Chicago sesh. And see all twelve neighborhood guides.