With baseball season officially underway, Chicagoans are going to be spending a lot of afternoons and evenings in Bridgeport (home of the White Sox) and Wrigleyville (home of the Cubs). But Chicago’s favorite crosstown rivalry goes further than baseball. Many Chicago residents are South Siders or North Siders for life.

Let’s find out how Bridgeport (a South Side incubator of Chicago politicians) and Wrigleyville (a perennial North Side party spot) compare.

Map of chicago, Wrigleyville and Bridgeport 

Homes and Pricing

2 detached homes in the Bridgeport neighborhood of Chicago

Bridgeport is one of those classic Chicago neighborhoods that was born from industrial roots and has bloomed into something new. Where warehouses once stood, the neighborhood is now replacing them with parks and residential developments. 

Single-family homes are the most common style of housing in this neighborhood, which means you can expect to find options with private yards and detached garages. If you’re interested in other home styles, you can still find a few low-rise condo buildings and two-flats scattered throughout Bridgeport. The median home sale price here is in the mid $300s, according to Neighborhoods.com data.

Wrigleyville has its fair share of luxury living, as reflected by its median sale price in the mid $400s. If you’re shopping for a home here, you can expect quite a few amenities but perhaps not as much space as other neighborhoods. Wrigleyville is a dense neighborhood with mostly attached homes (think condos and townhomes).

Winner: Bridgeport is the winner with the upper hand in both price and size.

Transportation and Walkability

The Addison Red Line stop in the Wrigleyville neighborhood of Chicago
Photo by Frank Romeo / Shutterstock.com

One of the top considerations for moving to a new neighborhood is how easy it is to get around. What will your commute to work look like? How easy will it be to run your errands around the neighborhood? 

Bridgeport earns a transit score of 61 and a walkability score of 81 from Walk Score, which means the neighborhood has solid public transit, and you can get most of your in-neighborhood errands done on foot. Bridgeport residents can get around using the city’s public transit—the CTA Orange and Red lines. The neighborhood is also crisscrossed with eight CTA bus routes, according to Walk Score. Bridgeport is also very bikeable with a score of 81 from Walk Score.

Wrigleyville is a pocket neighborhood—a part of the larger Lakeview community. The pocket neighborhood is served by two CTA red line stops: Addison and Sheridan, while the larger Lakeview neighborhood is served by the CTA Brown and Purple lines and a total of 16 bus lines, per Walk Score. Given its relatively small size, walking and biking around Wrigleyville is an easy feat.

Winner: Both neighborhoods are quite navigable, but Wrigleyville offers slightly more convenience in terms of public transit options, walkability, and bikeability.

Dining Out

The Jackalope Coffee and Tea House in the Bridgeport neighborhood of Chicago.

Home is where the heart is, but for a lot of people the stomach is the organ that really matters. When you’re searching for a place to put down roots, the restaurants you can walk to for date night, the coffee shops you can work in, and the brunch spots you can haunt on the weekend can make or break a neighborhood. 

Bridgeport has you covered with restaurants, coffee shops, and bars lining its stretches of Halsted Street, 31st Street, and 35th Street. On Halsted Street, you’ll find Jackalope Coffee & Tea House, Potsticker House, and nana. 31st Street also boasts ultra-cool bar Maria’s Packaged Goods, Fabulous Freddie’s Italian Eatery, and the greasy delights of Maxwell Street Depot. Down on 35th Street, you’ll find additional eateries serving hot dogs, tacos, and pizza all within walking distance of one another.

Wrigleyville may be a fairly small neighborhood, but it’s an entertainment destination, which means it’s packed with places to eat and drink. Fuel up on caffeine at Emerald City, or hit one of the bars lining Clark Street before or after the Cubs game. When it comes to eating, you can sate your carnivorous appetite at Argentine steakhouse Tango Sur, or stick close to Wrigley Field at spots like Big Star, Smoke Daddy BBQ, and Mordecai.

Winner: It’s a draw–a matter of taste, if you will.

Nightlife

Run the Jewels performs at The Metro in the Wrigleyville neighborhood of Chicago.
Photo by swimfinfan / CC BY-SA 2.0

There’s more to Bridgeport and Wrigleyville than their baseball fields, although those do provide plenty of nighttime entertainment. In Bridgeport, you’ll find plenty of open businesses along the neighborhood’s business corridor on South Halsted, as well as a proliferation of art galleries on Morgan Street and 35th Street. Plus you can grab a cold beer and cocktails at dive bars like Bernice’s Tavern and Mitchell’s Tap.

Wrigleyville’s 24-hour Taco Bell may be closed, but people certainly aren’t going to bed any earlier in the neighborhood. Get libations at organic brewery Uncommon Ground and take your pre- and post-game celebrations to Murphy’s Bleachers or The Cubby Bear

If bars aren’t your scene, Wrigleyville also has the Metro for live music and the Music Box Theatre for cinema.

Winner: It may be hard to pass a dull night in Bridgeport, but Wrigleyville is pretty much the undisputed king of nightlife in Chicago.

Education

The St. Jerome Elementary school located within the Bridgeport neighborhood of Chicago.

If you have kids, access to quality schools is going to be high on your list of neighborhood features. Bridgeport is served by three elementary schools—Healy, Ward J, and Perez—with a rating of eight or higher, according to GreatSchools. Just one elementary school, Greeley, serving Wrigleyville can say the same. 

Winner: Bridgeport earns the higher marks for its schools from GreatSchools.

Making a Choice

Whenever deciding between two neighborhoods, you have to ask yourself what really matters to you. Maybe you’re a diehard baseball fan and living within walking distance of your team’s field is a dream come true. Maybe the schools and the food matter more to you, or maybe the overall vibe–quiet or lively–is what settles it for you. Whatever you want in a neighborhood, both Bridgeport and Wrigleyville have plenty to offer. It’s up to you to determine which neighborhood feels like home.