The oldest, at least by virtue of having Chicago Liquor License #1 is the Burghoff. However, as many know, the Burghoff closed several years ago then re-opened after a few months with a new staff and modified menu. Some think it was done to get rid of its union servers, who were among the small handful of unionized waiters in the city.
However, I believe that the oldest continually-opened tavern in Chicago is Schaller's Pump located at 37th & Halsted. Schallers has been open since 1881 and I am fairly certain that it has been in the same family all this time.
The Green Door has been around for well over 100 years, but there have been periods when it was closed, changed hands, and even was operated as a grocery store. It is located at Huron & Orleans.
Another longtime, family-owned tavern/restaurant in Chicago is Stanley's, located at 43rd & Ashland. This business has been run by the same family since sometime in the 1930's. It's not as old as Schallers, but still pretty impressive.
The Green Mill has been on Broadway since 1907. If you saw Thief with James Caan, they filmed a bar scene there.
Pippin's on Rush Street has been there since 1949. The bartender, Marcy has been there over 25 years as well.
I would imagine that all those small neighborhood bars has been around for a lot of years as well. There was one on my block on the north side of Chicago just two doors down from me when I lived there.
Before transferring to Calif in 63, my watering hole was mostly
Simons on Clark St by Foster..I know Simon used to take care of
a lot of people in the Depression in the 30's and I remember his
buying out the shoe store and expanding the bar to two entryways
back in the 50's..I remember Fred and Daves, The High Life Inn,
Genglers as all neighborhood bars..Probably none left now..
Simons on Clark is still there. Here is a picture of the interior. Still looks like the 60's there. I later hung out at the Balmoral Clark Tap myself. It is closed now and reopened as another business.
There is a bar at Halsted & Schubert (2683 N. Halsted St.) called Alive One. My Grandfather used to go there in the 1930's & 1940's. I've looked at pix online and it seems it might have some original furnishings? Don't know. I live in the suburbs and plan to visit Chicago soon. I might stop in. Is anyone familiar with it?
My grandfather owned "the Main Gate" I'm fromt of the Crane Co works on Kedzie av in the 1920's. A shot n beer stop for the foundry workers that was almost continuously open.
He also owned a place called "Winslow's" on 33rd and Troop in Bridgeport that was in my family until it closed. That was a speakeasy during prohibition.
Exit at 1315 West North Avenue has been a bar since the mid 1960's that I know of. Since the building was built 1896, I am not sure what it was before. It was the Pine Inn in the mid 1960's. My father own it along my aunt. I think they owned in the mid to late 1950's but I can't be sure. I can remember going there with my Dad on Saturdays when he worked, and I was playing in the neighborhood. According to the Polk Directory it wasn't listed as any business in 1928-29. From the way the placed looked in the 60's, it looked like it has been a bar for a log time. Here you can take a look at the inside yourself.