The Bridgeport neighborhood began as a working-class area of Chicago with deep ties to the city’s political history. Over the years, the area has evolved into a growing hub of culture, art, food, and of course, White Sox pride.

This South Side enclave is accessible from downtown Chicago by train, bus, or even Water Taxi. It’s also near popular communities like Pilsen and Chinatown, making it the perfect jumping-off point for a day of neighborhood exploration.

We’ve compiled some of our favorite spots that make Bridgeport extra special, from a bustling hub for local artists to a Mexico City-inspired bakery to one of the city’s best taprooms. Get ready for a busy day in Bridgeport.

Start with the day with coffee and kayaks

Begin your day in Bridgeport by exploring one (or many) of their local cafes and roasteries.

Fat Peach Bakery is run by local partners Kerrie and David. Their homemade pastries (like the strawberry milk croissant) often sell out quickly (for good reason).

Bridgeport Coffee Centeris a classic, minimalist spot known for roasting and grinding their own beans.

Down the street, Jackalope Coffee‘s eccentric decor is anything but minimalist. The funky menu encompasses breakfast and lunch bites.

And if you’re in the mood for more of a diner feel, Stussy’s is a must for great food and great vibes.

Once you’re caffeinated, head to Wateriders Bridgeport for a relaxed morning paddle. Rent a kayak to explore the nearby Bubbly Creek and the South Branch of the Chicago River. Or join a tour to learn more about Chicago’s unique maritime history.

Stop for lunch and local brews

MARZ

When it’s time for a sit-down meal, there’s no shortage of places in Bridgeport. The breaded steak sandwich at Ricobene’s is a staple of the neighborhood enjoyed by locals and tourists alike.

The Bridgeport location of Antique Taco is another can’t-miss spot, featuring with handmade corn tortillas, inventive fillings, and plenty of seasonal margaritas. If you’re looking for Asian cuisine, then you have to stop by Potsticker House for their incredible handmade dumplings.

Finally, the original taproom of Marz Brewery (aka “The Mothership”) is located nearby in McKinley Park. Stop in for a beer and enjoy their dog-friendly beer garden or funky indoor bar space.

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Be a White Sox Fan for the day

Chicago White Sox play at Rate Field; photo by Giovanni Garnica
Chicago White Sox play at Rate Field; photo by Giovanni Garnica

If it’s baseball season, you’ll definitely want to grab tickets to cheer on the Chicago White Sox at Rate Field (though you might hear locals refer to it as Comiskey Park, the stadium’s original name when it opened in 1991).

At Rate Field, it’s all about the game day experience. Come early to tailgate in the stadium parking lot before the game, or swing by a local bar like ChiSox Bar & Grill or Cork & Kerry at The Park. Enjoy classic ballpark fare, tons of fan energy, and fireworks after every White Sox run.

Enjoy an arts and culture break

An open gallery night at Bridgeport Art Center
Photo courtesy Bridgeport Art Center

After lunch, make time to explore Bridgeport’s vibrant arts and culture scene. The Bridgeport Art Center is a vibrant hub for local artists across mediums, home to multiple galleries, a sculpture garden, an artisan cafe, and more. Check out the array of current exhibitions or visit during Third Fridays for an evening of open studios where you can meet the artists and chat about their work.

Nearby, Zhou B Art Center hosts 50 resident artists who showcase their works in public exhibitions throughout the year. The center has become a respected hub for contemporary art exhibitions and programming, while exploring the convergence of Eastern and Western art styles.

Bridgeport is also home to a variety of museums and galleries throughout the neighborhood, including the Chicago Maritime Museum and the Heritage Museum of Asian Art.

Time for dinner and a show

The Duck Inn patio
Photo by Kevin Hartmann

As the day winds down, you’ll want to stop and savor one of the many incredible restaurants for dinner in the neighborhood.

The Duck Inn, led by chef Kevin Hickey, is a favorite with a full menu of elevated options, including their signature rotisserie roasted duck or the duck dog, their ode to the classic Chicago-style hot dog.

If Italian is more your speed, Franco’s Ristorante and Gio’s Cafe and Deli are both wonderful options with handmade classics that will fit the bill.

JM Seafood blends authentic Cantonese flavors in an Asian fusion style that locals love. Enjoy Mediterranean fare at Zaytune Grill or dig into some of the city’s best slices can be found on 35th Street at Phil’s Pizza.

After dinner, Maria’s Packaged Goodsis a beloved community bar is the perfect spot for a nightcap.

Interior of Ramova Theater in Bridgeport
Ramova Theater in Bridgeport; photo by
Clayton Hauck

If you’re looking for some evening entertainment, the recently restored Ramova Theatre first opened in Bridgeport in 1929. With its iconic neon sign and historic architecture, the reinvigorated theatre also features a brewery, restaurant, and beer garden.

Alternatively, end your night at Charis Listening Barfor some vinyl tunes with a specialty craft cocktail or glass of wine: you’ve earned it.