Occupying a leafy corner of Damen Avenue in Chicago’s Roscoe Village neighborhood, Four Treys Tavern operated as far back as 1884 before closing during Prohibition. Owner Paul Seng reopened the Chicago dive bar in its current form in 1968 and years later met Colleen Flood, who eventually became his life partner, bar co-owner and unofficial “Mayor of Roscoe Village.” Flood moved to the area in the 1970s, met Seng and agreed to live with him above the bar.

Over her time in Roscoe Village, Flood opened a beauty salon and bought a number of rental units in the area with the hopes of establishing a family-friendly corner of the neighborhood at a time when gang crime was a prominent local issue. Renowned for backing down to no one, Flood set the strong tone that allowed Four Treys Tavern to exist and eventually benefit from the area’s upturn. Though Flood passed away in 2023, ownership remains in the Seng-Flood family and Flood’s neighborhood presence was so beloved that a ceremonial street sign just outside of the bar reads “Honorary Colleen J. Flood Way.”

Notably for a bar without a huge amount of exterior patio space, Four Treys Tavern is dog-friendly, meaning it is not uncommon to wade through a dog or two when opening the bar’s front door. The sign above that door is about as literal a sign can be for a Chicago dive bar named ‘Four Treys Tavern,’ depicting a four-of-a-kind poker hand filled with 3’s atop a very casino-like green background. Holiday string lights trace the bar’s exterior just under a short shingled roof that trims the structure.

As Chicago dive bars go, Four Treys Tavern is a classic experience, down to the drop ceiling, beer mirrors and prominent corner placement that makes it a magnet for locals. A handful of mounted television mix with Chicago Bears gear, at least one cartoon depiction of Harry Caray and an immaculate Miller Genuine Draft pool table light shaped in the form of a NASCAR stock car.

Just inside the front door, the main Four Treys Tavern Tavern bar is a long, wraparound counter that curves into itself to create either welcome or unwelcome sightlines for drinkers perched on opposite sides of the bar. The shingled roof motif is replicated behind the bar, another such ledge accompanying another such set of string lights atop the bar’s liquor selection. A bar of draft taps complement a beer selection filled with Chicago dive bar classics.

A small secondary space is filled almost completely by the bar’s pool table and digital dart board, only a handful of hightop tables here wedged into the remaining space. Golden Tee can also be found here and the Four Treys Tavern square footage is mostly exhausted at this point, a number of short tables and padded bar seats accounting for the balance of the bar’s amenities.