In January 1896, alumni from the Omega Chapter at the old University of Chicago approached members of the Omega Society and announced to them that they had never voluntarily surrendered their charter. They therefore considered themselves an active chapter and asked the Omega Society if they would like to be initiated.
The Omega Society petitioned the Executive Council of Psi Upsilon for a charter. The Executive Council recommended that the charter be granted and forwarded the petition to the active chapters. Unfortunately the petition failed as 4 chapters voted against it. At this same time the Omega Society merged with a group which had been petitioning to join Sigma Chi. With their numbers increased substantially, the Omega Society once again petitioned for a charter in the Spring of 1895. They were again denied. This process was repeated at the 1895 Annual Convention, held in May.The Omega Society replied in the affirmative and on 31 January 1896, a formal initiation ceremony was held.On 6 February 1896, the Executive Council of Psi Upsilon responded by declaring the Omega Chapter had ceased to exist in 1887 and therefore could not initiate new members. The alumni of the Omega protested vigorously, but in November 1896, the Omega Society announced that it would “withdraw” from Psi Upsilon and forward a new charter petition to the Executive Council. After much wrangling with various chapters, specifically the Lambda, Eta, and Mu, the petition was unanimously approved on 22 October 1897. The chapter was formally reestablished on 24 November 1897. Rev. Samuel Goodale, one of the founding fathers of Psi Upsilon, was in attendance at the reestablishment.
Since April 1917, The Omega of Psi Upsilon has been located on S. University, across the street from the College. It was constructed for the purpose of housing the Omega chapter, designed by architect Jeremiah K. Cady, (Chi, 1876), and paid for by generous brothers.
The Omega Society rented four rooms on the second floor of a building at 60th and Ellis and in March 1894
The Omegas at this time had outgrown their rooms on 60th and Ellis and moved north to quarters directly across from the athletic field at 56th and Ellis. This habitation was only temporary as the Omega Society moved to rent a chapter house at 5528 Monroe Avenue (now Kenwood Avenue). This was the first Omega Chapter House. It was secured for $75.00 a month.
Within their first 15 years the Omega would relocate 4 times. In 1897, they moved to 5660 Madison Avenue, then in 1903 to 6106 Woodlawn Avenue, then in 1909 5824 Woodlawn Avenue, followed by, in 1910, 5536 Dorchester Avenue, then finally to 5845 Dorchester Avenue. The first 15 years had been a great success for the Omega all things but locating satisfactory living quarters. To remedy that problem, in 1910 the Omega began a house fund. By 1916, the Omega had raised enough money to purchase the property at 5639 University Avenue. Through the generosity of a number of brothers, the money was raised to build a chapter house, with Jeremiah K. Cady, Chi 1876, serving at the architect. Construction began in earnest in the summer of 1916 and the Omega moved into their new house on 1 April 1917.
During the First World War, the Omega saw 108 members serve the cause of freedom. The chapter house itself was leased to the government for the period of hostilities and, though membership was low at times, the Omega endured.
This prosperity continued until the time of the Second World War. The Omega once again saw its membership levels drop and in 1943, the Omega turned its house over to the management of the University. Many Omega fought for their country in the War and some did not return home. Following the war, the Omega once again regained control of their house and regrouped. For much of the post-war period, the Omega was a bastion of athletic prowess. In the 1957 edition of Cap and Gown, the University yearbook, the Omega was dubbed, “The New York Yankees of Fraternity Athletics.” They have also gained many academic distinctions, including the 1984 election of Sean Mahoney as a Rhodes Scholar. The Omega has prospered through difficult times in the 1960s and 1970s and has emerged all the stronger. They have lasted to the present day by providing young men with the opportunity for a unique social and intellectual interaction within the confines of the University of Chicago.