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A variety of Sichuan dishes spread on a table.
A Place By Damao dials up the spice on its Chengdu-inspired dishes.
A Place By Damao

Where to Eat and Drink in Bridgeport

The South Side neighborhood is brimming with diverse options

by Jeffy Mai
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A Place By Damao dials up the spice on its Chengdu-inspired dishes.
| A Place By Damao
by Jeffy Mai

Bridgeport is one of Chicago’s most diverse community areas and as a result, its best restaurants cover a wide variety of flavors. Some places have been operating for decades while others are relative newcomers, but they all help make the South Side neighborhood a hotbed for quality dining. Their focuses range from spicy Sichuan specialties and Italian red sauce dishes to iconic Chicago foods like tavern-style pizza and Polish sausage. So no matter what Chicagoans are in the mood for, they’ll find it and more in burgeoning Bridgeport, the home of the Chicago White Sox and Guaranteed Rate Field.

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Big Boss Spicy Fried Chicken

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An eye-popping façade helps draw diners in for fiery fried chicken at this Bridgeport newcomer. Owner Jassy Lee adopts the Belizean method of seasoning the meat overnight before frying and then coating it in a Nashville-style sauce. Five spice levels on the chicken, also available as a sandwich, are offered. The restaurant’s decor also overloads the senses with colorful graffiti artwork.

2520 S Halsted St, Chicago, IL 60608
(312) 877-5031
(312) 877-5031
A fried chicken sandwich.
Big Boss Spicy Fried Chicken packs a punch.
Big Boss Spicy Fried Chicken [Official Photo]

Also featured in:

Ricobene's

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Old-school Italian-American fare is the appeal of this family-owned establishment that’s been in operation since 1946. Loyal customers pack the large dining room for what some proclaim to be the best sandwich in the world — the breaded steak sandwich. This meaty legend is worth getting messy for and features breaded steak, mozzarella, tomato sauce, and giardiniera on a Turano French roll. It’s also open late.

252 W 26th St, Chicago, IL 60616
(312) 225-5555
(312) 225-5555

Also featured in:

Sugar Shack

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Adults and children alike flock to this walk-up dessert stand for a sugar high. The signature funnel cake sundae is an oversized treat capable of feeding several people, and other highlights include banana splits and blizzards. No matter the choice, though, customers are bound to walk away happy at this essential summertime spot.

630 W 26th St, Chicago, IL 60616
(312) 225-6568
(312) 225-6568
A funnel cake sundae.
Indulge in a variety of ice creams and desserts at Sugar Shack.
Sugar Shack [Official Photo]

Also featured in:

A Place By Damao

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Sichuan specialties are available at many Chinese restaurants around the city but this tiny storefront delves into the unexplored street food of Chengdu. Savor hot pot mixes, spicy braised offal-y items, and regional dishes like spare ribs and handmade bell dumplings. The bold flavors are designed to set the mouth afire so be ready for the heat or order the water jelly cake dessert to offset it.

2621 S Halsted St #1, Chicago, IL 60608
(312) 929-2088
(312) 929-2088
A platter of spare ribs.
A Place By Damao offers spicy dishes from the streets of Chengdu.
A Place By Damao [Official Photo]

Also featured in:

The Duck Inn

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Owner Kevin Hickey’s lauded neighborhood tavern blends classic Midwestern comfort cuisine with his chef-driven technique. The menu boasts playful-yet-refined bites, such as a duck-fat hot dog and a hamburger sandwich, as well as a signature rotisserie duck served with duck jus reduction. The retro-inspired space, housed inside a pre-Prohibition era building, is equally enthralling while the lovely back patio is an ideal place to hang out during the summer.

2701 S Eleanor St, Chicago, IL 60608
(312) 724-8811
(312) 724-8811

Also featured in:

Gio's Cafe and Deli

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Half deli and half restaurant, Gio’s specializes in hearty Italian fare. Grab a seat at one of the checkered tables and feast on hearty portions of arancini, chicken parm, rigatoni alla vodka, seafood pastas, and more. Diners are welcome to bring their own alcohol too.

2724 S Lowe Ave, Chicago, IL 60616
(312) 225-6368
(312) 225-6368

Also featured in:

Bridgeport Bakery

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Bridgeport briefly lost a pillar of the community when this longstanding bakery closed its doors late last year. Fortunately, a new owner quickly emerged and brought back everyone’s favorite assortment of pastries. Indulge in paczki, bacon buns, maple-bacon doughnuts, and other new additions.

2907 S Archer Ave, Chicago, IL 60608
(773) 523-1121
(773) 523-1121

Also featured in:

Franco's Ristorante

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Although Franco’s looks like a relatively new restaurant thanks to a remodel in 2016, it has actually been serving Bridgeport residents for more than 30 years. The charmingly modern-yet-vintage space is home to housemade Italian staples, such as thick-cut pork chop vesuvio, light gnocchi, chicken giardiniera, and tiramisu.

300 W 31st St, Chicago, IL 60616
(312) 225-9566
(312) 225-9566
A plate of pork chop vesuvio on a table with a glass of red wine.
Dine on Italian specialties at Franco’s Ristorante.
Franco’s Ristorante [Official Photo]

Also featured in:

Kimski

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Disparate cuisines collide for a unique mashup at Kimski. The Korean-Polish fusion restaurant delivers street-food-inspired dishes like Polish sausages topped with “kraut-chi”; smoked and fried wings glazed in sweet and spicy sauce; and a marinated beef sandwich with shishito peppers, onions, Muenster cheese, and gochujang butter. The food can also be taken next door to Maria’s Packaged Goods and paired with the extensive beer list.

954-960 W 31st St, Chicago, IL 60608
(773) 823-7336
(773) 823-7336

Also featured in:

Maria's Packaged Goods and Community Bar

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The neighborhood’s most well-known bar also offers one of the city’s largest beer lineups. Enjoy dozens of craft brews alongside a selection of daily-changing cocktails in a small and intimate setting. Hungry patrons can order food from Kimski, and there’s a liquor store in the front of the space for on-the-go libations. Chicagoans call this set-up a packaged good store, a place that’s part bar, part liquor store.

960 W 31st St, Chicago, IL 60608
(773) 890-0588
(773) 890-0588

Also featured in:

Maxwell Street Depot

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Late-night cravings should be satiated with greasy delights and in Bridgeport, Maxwell Street Depot is the best place to get it. This 24-hour institution dishes out some of the city’s most iconic foods, including juicy bone-in pork chop sandwiches, Polish sausages, and Chicago-style hot dogs.

411 W 31st St, Chicago, IL 60616
(312) 326-3514
(312) 326-3514

Also featured in:

Han 202

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Chinatown is the obvious central hub for Chinese food in Chicago but Bridgeport has its fair share of standouts. Head to this fusion eatery for a $35 four-course prix fixe experience. The kitchen’s contemporary approach to traditional flavors results in dishes like soft shell crab with sweet chili sauce; rainbow trout with sweet and sour sauce; and rack of lamb with bonito plum sauce. An added bonus: Alcohol is BYO.

605 W 31st St, Chicago, IL 60616
(312) 949-1314
(312) 949-1314

Bernice's Tavern

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Dark, cozy, and staffed by friendly folks, Bernice’s Tavern has all the traits of a good dive. Stop into the timeless watering hole for a low-key evening full of cheap beer and jukebox tunes. The bar also hosts open mic and bingo nights.

3238 S Halsted St, Chicago, IL 60608
(312) 961-5516
(312) 961-5516

Also featured in:

Phil's Pizza

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Thin-crust is the preferred pizza style for many Chicagoans and few places are as highly regarded as this longtime specialist. South Siders love the satisfying crispy pies, which are topped with a variety of ingredients like sliced beef, giardiniera, and housemade fennel-flecked sausage. Just make sure to bring a few bills; Phil’s is cash only.

1102 W 35th St, Chicago, IL 60609
(773) 523-0947
(773) 523-0947

Also featured in:

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Big Boss Spicy Fried Chicken

2520 S Halsted St, Chicago, IL 60608

An eye-popping façade helps draw diners in for fiery fried chicken at this Bridgeport newcomer. Owner Jassy Lee adopts the Belizean method of seasoning the meat overnight before frying and then coating it in a Nashville-style sauce. Five spice levels on the chicken, also available as a sandwich, are offered. The restaurant’s decor also overloads the senses with colorful graffiti artwork.

2520 S Halsted St, Chicago, IL 60608
(312) 877-5031
(312) 877-5031
A fried chicken sandwich.
Big Boss Spicy Fried Chicken packs a punch.
Big Boss Spicy Fried Chicken [Official Photo]

Ricobene's

252 W 26th St, Chicago, IL 60616

Old-school Italian-American fare is the appeal of this family-owned establishment that’s been in operation since 1946. Loyal customers pack the large dining room for what some proclaim to be the best sandwich in the world — the breaded steak sandwich. This meaty legend is worth getting messy for and features breaded steak, mozzarella, tomato sauce, and giardiniera on a Turano French roll. It’s also open late.

252 W 26th St, Chicago, IL 60616
(312) 225-5555
(312) 225-5555

Sugar Shack

630 W 26th St, Chicago, IL 60616

Adults and children alike flock to this walk-up dessert stand for a sugar high. The signature funnel cake sundae is an oversized treat capable of feeding several people, and other highlights include banana splits and blizzards. No matter the choice, though, customers are bound to walk away happy at this essential summertime spot.

630 W 26th St, Chicago, IL 60616
(312) 225-6568
(312) 225-6568
A funnel cake sundae.
Indulge in a variety of ice creams and desserts at Sugar Shack.
Sugar Shack [Official Photo]

A Place By Damao

2621 S Halsted St #1, Chicago, IL 60608

Sichuan specialties are available at many Chinese restaurants around the city but this tiny storefront delves into the unexplored street food of Chengdu. Savor hot pot mixes, spicy braised offal-y items, and regional dishes like spare ribs and handmade bell dumplings. The bold flavors are designed to set the mouth afire so be ready for the heat or order the water jelly cake dessert to offset it.

2621 S Halsted St #1, Chicago, IL 60608
(312) 929-2088
(312) 929-2088
A platter of spare ribs.
A Place By Damao offers spicy dishes from the streets of Chengdu.
A Place By Damao [Official Photo]

The Duck Inn

2701 S Eleanor St, Chicago, IL 60608

Owner Kevin Hickey’s lauded neighborhood tavern blends classic Midwestern comfort cuisine with his chef-driven technique. The menu boasts playful-yet-refined bites, such as a duck-fat hot dog and a hamburger sandwich, as well as a signature rotisserie duck served with duck jus reduction. The retro-inspired space, housed inside a pre-Prohibition era building, is equally enthralling while the lovely back patio is an ideal place to hang out during the summer.

2701 S Eleanor St, Chicago, IL 60608
(312) 724-8811
(312) 724-8811

Gio's Cafe and Deli

2724 S Lowe Ave, Chicago, IL 60616

Half deli and half restaurant, Gio’s specializes in hearty Italian fare. Grab a seat at one of the checkered tables and feast on hearty portions of arancini, chicken parm, rigatoni alla vodka, seafood pastas, and more. Diners are welcome to bring their own alcohol too.

2724 S Lowe Ave, Chicago, IL 60616
(312) 225-6368
(312) 225-6368

Bridgeport Bakery

2907 S Archer Ave, Chicago, IL 60608

Bridgeport briefly lost a pillar of the community when this longstanding bakery closed its doors late last year. Fortunately, a new owner quickly emerged and brought back everyone’s favorite assortment of pastries. Indulge in paczki, bacon buns, maple-bacon doughnuts, and other new additions.

2907 S Archer Ave, Chicago, IL 60608
(773) 523-1121
(773) 523-1121

Franco's Ristorante

300 W 31st St, Chicago, IL 60616

Although Franco’s looks like a relatively new restaurant thanks to a remodel in 2016, it has actually been serving Bridgeport residents for more than 30 years. The charmingly modern-yet-vintage space is home to housemade Italian staples, such as thick-cut pork chop vesuvio, light gnocchi, chicken giardiniera, and tiramisu.

300 W 31st St, Chicago, IL 60616
(312) 225-9566
(312) 225-9566
A plate of pork chop vesuvio on a table with a glass of red wine.
Dine on Italian specialties at Franco’s Ristorante.
Franco’s Ristorante [Official Photo]

Kimski

954-960 W 31st St, Chicago, IL 60608

Disparate cuisines collide for a unique mashup at Kimski. The Korean-Polish fusion restaurant delivers street-food-inspired dishes like Polish sausages topped with “kraut-chi”; smoked and fried wings glazed in sweet and spicy sauce; and a marinated beef sandwich with shishito peppers, onions, Muenster cheese, and gochujang butter. The food can also be taken next door to Maria’s Packaged Goods and paired with the extensive beer list.

954-960 W 31st St, Chicago, IL 60608
(773) 823-7336
(773) 823-7336

Maria's Packaged Goods and Community Bar

960 W 31st St, Chicago, IL 60608

The neighborhood’s most well-known bar also offers one of the city’s largest beer lineups. Enjoy dozens of craft brews alongside a selection of daily-changing cocktails in a small and intimate setting. Hungry patrons can order food from Kimski, and there’s a liquor store in the front of the space for on-the-go libations. Chicagoans call this set-up a packaged good store, a place that’s part bar, part liquor store.

960 W 31st St, Chicago, IL 60608
(773) 890-0588
(773) 890-0588

Maxwell Street Depot

411 W 31st St, Chicago, IL 60616

Late-night cravings should be satiated with greasy delights and in Bridgeport, Maxwell Street Depot is the best place to get it. This 24-hour institution dishes out some of the city’s most iconic foods, including juicy bone-in pork chop sandwiches, Polish sausages, and Chicago-style hot dogs.

411 W 31st St, Chicago, IL 60616
(312) 326-3514
(312) 326-3514

Han 202

605 W 31st St, Chicago, IL 60616

Chinatown is the obvious central hub for Chinese food in Chicago but Bridgeport has its fair share of standouts. Head to this fusion eatery for a $35 four-course prix fixe experience. The kitchen’s contemporary approach to traditional flavors results in dishes like soft shell crab with sweet chili sauce; rainbow trout with sweet and sour sauce; and rack of lamb with bonito plum sauce. An added bonus: Alcohol is BYO.

605 W 31st St, Chicago, IL 60616
(312) 949-1314
(312) 949-1314

Bernice's Tavern

3238 S Halsted St, Chicago, IL 60608

Dark, cozy, and staffed by friendly folks, Bernice’s Tavern has all the traits of a good dive. Stop into the timeless watering hole for a low-key evening full of cheap beer and jukebox tunes. The bar also hosts open mic and bingo nights.

3238 S Halsted St, Chicago, IL 60608
(312) 961-5516
(312) 961-5516

Phil's Pizza

1102 W 35th St, Chicago, IL 60609

Thin-crust is the preferred pizza style for many Chicagoans and few places are as highly regarded as this longtime specialist. South Siders love the satisfying crispy pies, which are topped with a variety of ingredients like sliced beef, giardiniera, and housemade fennel-flecked sausage. Just make sure to bring a few bills; Phil’s is cash only.

1102 W 35th St, Chicago, IL 60609
(773) 523-0947
(773) 523-0947

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