10 Long Standing Mom and Pop Small Businesses in Chicago

Enjoy these 10 Chicago mom and pop small businesses!

The largest city in the Midwest, Chicago, boasts such an impressive skyline that it’s hard to believe that the metropolis was once a humble farming town. Before the major corporations and the skyscrapers that house many of them were built, mom and pop businesses dotted Chicagoland, from the suburbs to downtown and the Loop.

Considered the railway hub of the U.S. and one of the country’s greatest cultural melting pots, Chicago has worn many hats since its incorporation in 1837. The Great Chicago Fire of 1871 destroyed much of Chicago’s city center and small businesses. A total of 18,000 buildings, but the city was rebuilt to become more vibrant and culturally significant than ever.

Today, the Windy City is a long-standing mecca for deep-dish pizza, blues music, and baseball. It also remains the home of a wide variety of family owned small businesses, many of which are now famous Chicago landmarks.

1. Shinnick’s Pub

Photo Credit: Facebook/shinnickspub

The building that this well known pub sits in were both resurrected at the same time in the late 1880’s. This mom and pop went through several owners who tried their luck owning the pub until, in 1938, George & Mary Shinnick took it over after prohibition. Ever since that day it has moved through generations of Shinnicks, and is now owned by the third generation of siblings. Nine of them to be exact.

 

2. Belmont Barbershop

Photo Credit: Facebook/belmontbarchicago

For an old-fashioned shave or haircut in a decidedly unpretentious environment, Belmont Barbershop is your best bet. Independently owned since 2005, the Roscoe Village neighborhood mom and pop shop is one of Chicago’s best. So, if you’re ever in the area and find yourself in need of a cut, look no further!

 

3. Cone

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One of the youngest businesses on this list, Cone is a family owned gourmet ice cream parlor that serves up sweet treats with a distinctly Irish flair. Born in Ireland, owner and founder, Sean McGuire, opened his West Loop shop in 2013. The family-friendly treat shop’s menu features European-style soft serve and hand-scooped ice cream sandwiches for the kids, and liquor-infused delicacies for adults. When you dine in at the 1047 West Madison Street eatery, you can have a pint of Guinness to complement your soft serve waffle cone. Or you can even choose a dash of Irish cream or whiskey as a sundae topping. Slainte!

 

4. George’s Hot Dogs

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The Chicago-style hot dog is nearly as famous as the city’s deep dish pizza. The Chicago dog is a virtual meal in itself – a classic beef hot dog in a bun, topped with relish, white onions, yellow mustard, sliced tomatoes, and a pickle spear. Over the years, hot dog stands have become ubiquitous across Chicago, but few have enjoyed the longevity of George’s. The Damen Avenue restaurant has been family owned and operated since 1948. George’s Hot Dogs offers daily specials and has garnered a variety of awards from far-flung publications and websites. That includes the likes of GrubHub and The Chicago Tribune.

 

5. Medina Lawncare

Photo Credit: medinalawncare.com

Established in 1967 by Carlos Medina and his two brothers, Medina Lawncare is a true to form family owned business. Medina Jr., now second generation owner of the landscaping company, had been working for his father since the age of 12. It was 20 years ago that he decided to take it over to keep the business in the family, and he hasn’t looked back since. If you’re in the market for some beautiful landscaping with deep rooted history, look them up!

 

6. Windy City Hardware

Photo Credit: Facebook/Windy-City-Hardware

Truly a mom and pop business, Windy City Hardware has become a sort of community center in Bridgeport since its opening in 2008. Husband and wife, Jerry and Windy Masterson, serve as the hardware store’s small business owner team.

Even though the shop is small, they expanded Windy City Hardware to encompass bike gear and repair services after noting a high neighborhood demand. Their shop, at 3364 S. Halsted remains to be one of Bridgeport’s go-to bike repair shop.

 

7. Twin Anchors Restaurant & Pub

Photo Credit: twinanchorsribs.com

Locally owned and operated since 1932, Twin Anchors is world-famous, yet decidedly unpretentious. Housed in a classic brick 1880s building at 1655 N. Sedgwick Street, the restaurant was reportedly a favorite of Frank Sinatra. The Twin Anchors menu features sandwiches, burgers, baby-back ribs, and salads.

 

8. Home Team Pizza

Photo Credit: Facebook/Home Team Pizza

Chicagoans take their pizza seriously, so it’s no surprise that several pizza shops are counted among the city’s longest standing mom and pop businesses. The owners of Home Team Pizza have made Chicago their home for several generations, opening the West Ohio Street eatery in 1975. You’ll find wood oven-baked pizza, salads, sandwiches, decadent desserts, and more at Home Team Pizza. They  also offer a convenient delivery option seven days a week.

 

9. Hagen’s Fish Market

Photo Credit: Facebook/Hagen’s Fish Market

Since 1946, Hagen’s Fish Market has been the go-to place for Chicagoans who love fresh seafood. Located at 5635 W. Montrose Avenue, Hagen’s is steeped in tradition, offering natural hardwood smoked seafood prepared using family recipes. Those recipes remain closely guarded by the Hagen family. At Hagen’s, you can pick up fresh fish to prepare at home or try out the restaurant’s famous battered shrimp, cod, and perch.

 

10. Daley’s Restaurant

Photo Credit: DNAinfo/Sam Cholke

Although it carries the name of two of Chi-Town’s most notable mayors, Richard J. Daley and his son Richard M., Daley’s Restaurant was actually named after its founder, John Daley, a former iron worker originally from Ireland. John Daley established his namesake restaurant in 1892; and today, Daley’s is considered the oldest restaurant in Chicago. The Daley’s building at 809 E. 63rd Street is actually the second incarnation of the renowned diner. In 1918, a pair of Greek immigrants took it over, and have kept it in the family ever since. And keeping the name that has carried it through the years.

For even more small businesses with a deep-rooted history in their city here are 10 more mom & pops in New York!

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