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Pickle Barrel Old Towm
The Pickle Barrel was founded by Leo Osher who was a successful restauranteur . He ran multiple Jewish style restaurants and delis in the Chicago area from 1950 until his death.
. Osher was a Chicago native who grew up in the west side. He graduated from Roosevelt High School. In 1950, he opened the Corned Beef Center (A small deli) at 3352 Broadway in Chicago. It was in business for 10 years.
In 1960, he opened the Pickle Barrel at 1423 N. Wells Street in Chicago. The walls were decorated with oddities and antiques. At each table, there was a barrel of pickles, a bucket of popcorn and a small barrel of Kosher dill pickles.
In an average week, the Pickle Barrel would go through 10 fifty pound barrels of pickles and 400 pounds of popcorn. The menu included deli sandwiches, ribs, fried shrimp, and sloppy joes. Balloon artists entertained the kids and pitcher of beers the adults.
At one time, there multiple Pickle Barrel Restaurants in the Chicago area. These included one on Oak Street, one at Howard and Western, one at the Park Forest Plaza in Park Foresr, Illinois, one at 240 Skokie Boulevard in Northbrook.
Osher sold the chain in the 1970’s. He and his son opened Barnum and Baegel Restaurant at 4700 West Dumpster in Skokie. He died April 20, 199.

Pickle Barrel Restaurant Howard and Western Chicago

Pickle Barrel on Oak Street