Wednesday, February 3, 2021

A Brief History of the Pickle Barrel Restaurant.

The Pickle Barrel restaurant was Leo Osher's brainchild, who operated several Jewish-style restaurants and delis in the Chicagoland area from 1950 until his death.

A native of Chicago, Mr. Osher grew up on the West Side and graduated from Roosevelt High School. After serving in the U.S. Army during World War II, he opened the Corned Beef Center, a small deli at 3352 Broadway at Roscoe Street in 1950. It remained in business for 10 years.
He opened the Pickle Barrel in 1960. The quirky restaurant was right at home on the popular streets of Chicago's Old Town (80+ photos). The walls were decorated with oddities and antiques. Guests were greeted with a barrel of pickles for snacking and a bucket of popcorn on each tabletop.

The Pickle Barrel NEVER served peanuts on the tables so there were no shells on the floor. The "Ground Round" and "Chances R" restaurants had peanuts and the shells were thrown on the floor. 
At the Pickle Barrel, guests were seated with a small barrel of pickles, eat all you want, and a big bowl of popcorn. They sold a lot of beer.

The Old Town Pickle Barrel.

The Old Town Pickle Barrel Menu, 1423 North Wells Street, Chicago. 

The Pickle Barrel, in an average week, would go through 10 fifty-pound barrels of pickles (26,000 lbs a year)—each barrel containing about 1,200 pickles and 400 pounds of popcorn (20,800 lbs a year). The menu featured deli sandwiches and decidedly non-Jewish deli fare like ribs, fried shrimp, and sloppy Joes. Balloon artists entertained the kids, and pitchers of beer entertained the adults.

In 1964, Leo Osher was named the Pickle Man of the Year. "He was a natural candidate," said William Moore, retired executive vice president of the Pickle Packers International, then a national trade association, which bestowed the award on Mr. Osher. As the owner of Chicago's popular Pickle Barrel restaurant in Old Town at 1423 N. Wells Street. Osher played along good-naturedly with the publicity stunt, which, mercifully, only went so far. "I don't think he had to wear a banner or tiara," said his daughter-in-law, Ellyn Osher.
Oak Street Pickle Barrel

Osher opened four more Pickle Barrel locations, including one on Oak Street and one at Howard and Western. 

Success did not come without risks, however. In March 1964, two armed bandits robbed the Pickle Barrel, making off with $2,000. The two men forced four male patrons into a walk-in refrigerator until the crime was complete, Mr. Osher told police, according to a news report at the time. "He just said that was a terrible thing," said an employee of 21 years, Sue Glaser, manager of the Barnum & Bagel restaurant in Skokie, Illinois. "He never really talked a lot about it after that."

"They hit a niche. It was a simple menu with high energy and a lot of fun and value," said restaurateur Richard Melman, founder and chief executive officer of Lettuce Entertain You Enterprises.
Howard and Western Pickle Barrel
In the late 1970s, Osher sold the Pickle Barrel restaurant chain.

Osher was a resident of Skokie. He and his son Michael opened the Barnum & Bagel restaurant at 4700 West Dempster Street in Skokie. They briefly considered naming it "20th Century Lox."

Osher died Tuesday, April 20, 1999, of complications from heart surgery at a hospital in California where he had a second house. He was 79.

The Pickle Barrel Restaurant, Old Town, 1423 North Wells Street, Chicago, IL
The Pickle Barrel Restaurant, 7574 North Western Avenue, Chicago, IL
The Pickle Barrel Restaurant, 50 East Oak Street, Chicago, IL
The Pickle Barrel Restaurant, Park Forest Plaza Shopping Center, Park Forest, IL
The Pickle Barrel Restaurant, 240 Skokie Highway, Northbrook, IL

Compiled by Dr. Neil Gale, Ph.D.


  1. Western Avenue is 2400 West, runs North-South from 7579 North to 11859 South

    The Howard & Western Shopping Center Address is at 7562 N. Western Avenue, Chicago.

    1. My close friends spider lawerance and carl cafferillo worked behind the bar doing magical tricks and ballons while bartending.i went to school with carl.

  2. Replies
    1. Not to my knowledge. I have two menus. We ate often at the Pickle Barrel on Howard & Western, Chicago.

    2. The PB at Howard & Western had a weekend,?/Sunday? all you could eat brunch if lox, cream cheese, sliced tomatoes and onions, and of course pickles for probably less than $5 that I went to often with two Jewish fellow Northwestern grad students. Wow! What I wouldn't give to do that one more time before I kick the bucket!!!

  3. Grew up eating at Howard & Western location and never had any pizza..never saw it on menu...

  4. Loved eating as well as GOOD food!

  5. Saw the restaurant in the movie Harry and Tonto!

  6. I loved the Oak Street location. It was a treat we would go to the hair salon across the street then to the Pickle Barrel for lunch.

  7. My parents ussed to take me to the one on Wells when I came home from boarding school. Was so much fun walking up and down wells checking out all the hippie shops. Remember Paul Bunyans?

  8. Does anyone know the connection to the Shreveport location?

    1. The Pickle Barrel restaurant (1993-2015) in Shreveport, LA, has no relation with the Chicago Pickle Barrel restaurant.

  9. There appears to be 2 address for The Pickle Barrel on N. Wells St... 1452 & 1423 N. Wells. I remember the one that was on the east side of the street which was 1423.

  10. Didn’t Ben Kramer buy the chain?

  11. I grew up on Clairemont st right behind the cta turn around on western ave, me and my brothers would go there a lot as kids...I have found memories of that place! They just don't make them like that anymore!

  12. *Such as* ribs, etc, not *like* ribs, etc.

  13. Went there as a kid in the 70's. I clearly remember them serving shelled peanuts and popcorn in baskets and projecting cartoons above the tables on a screen. Their burgers were too notch.

    1. As stated in the article:
      "The Pickle Barrel NEVER served peanuts on the tables so there were no shells on the floor. The "Ground Round" and "Chances R" restaurants had peanuts and the shells were thrown on the floor. At the Pickle Barrel, guests were seated with a small barrel of pickles, eat all you want, and a big bowl of popcorn. They sold a lot of beer."

      Here's why The Ground Round fits your description:
      The local Ground Round was located at the southwest corner of Crawford and Lincoln Avenues in Lincolnwood.

      Peanuts and shell-strewn floors: This was The Ground Round's signature feature for many years. They provided complimentary peanuts, and throwing the shells on the floor was encouraged, creating a unique and casual atmosphere.

      Cartoon screenings: Many Ground Round locations had screens that played classic cartoons, making them popular destinations for families with children.


The Digital Research Library of Illinois History Journal™ is RATED PG-13. Please comment accordingly. Advertisements, spammers and scammers will be removed.