The Upsilon Sigma Chapter of the Phi Beta Sigma Fraternity was chartered on September 11, 1927.

The chapter immediately flourished and became a driving force in the African American community in Chicago, Illinois.  In the beginning, the chapter met at a funeral establishment on South Indiana avenue.

The chapters annual Drikel Ball on the the Thursday immediately following Thanksgiving opened the social calendar for formal events in Chicago.

In 1949, a program was started to buy a fraternity house.  The tireless effort of brothers in the chapter resulted in the purchase of "The Sigma House" at 4941 S. Dr. Martin Luther King Drive.

Upsilon Sigma hasbeen the mother chapter of the Great Lakes Region.  During the administration of brothers Chester Riley and Clarence Johnson, both Directors of the Great Lakes Region (1974 - 1980) more than 61 chapters of the Phi Beta Sigma Fraternity were chartered or reclaimed throughout the region.

Visionary Leadership was provided by:

• Bro. Summer Colum, MD
• Bro. Austin Gray, MD
• Bro. Milton Johnson, MD
• Bro. William M. Jones
• Bro. George W. Lawrence, JD
• Bro. Hugh Fisher Lewis
• Bro. U.C. McClerkins
• Bro. George W.  Prince
• Bro. John E. Smith