Chicago, Illinois

It all started with the birth of Margaret Downey on 14 January 1798. She then married Christopher Gregory in Creggan Parish, County Armagh, Ireland on 6 Jan 1814. According to County Armagh records, they had ten children. Of the ten, only four have been traceable – Francis, John, Edward and James Gregory. One daughter, Allice, may have stayed in Ireland and married Michael Morris, but that has to be confirmed.

Francis was born in 1820, followed by John in 1822, James in 1827 and Edward in 1839. Based on John Gregory’s naturalization papers, he arrived in the US in 1844, and was naturalized in New York on 11 Dec 1849. According to the US Census, all the brothers were residents of New York in 1850 with the exception of Edward who remained in Ireland. Naturalization data has not yet been confirmed for James and Francis. It is assumed that they were naturalized in New York as well.
James and Francis, probably enticed by the Illinois Central Railroad’s promise of inexpensive farmland and steady railroad work, relocated to the new town of Amboy in Lee County, IL. The two brothers became farmers and worked for the Illinois Central until their deaths at the turn of the century.

John, on the other hand, took up a different mode of transportation as a livelihood. He may originally have learned the shipbuilding trade in Ireland, because Armagh is not far from Belfast, a major shipping port. Or he may have heard about the booming town of Chicago and preferred ships to trains. Nevertheless, he relocated to Sheboygan, WI sometime in the mid 1850’s. Sheboygan, chartered in 1853, was one of several Wisconsin towns sharing the waters of Lake Michigan that served as a ship-building center for Chicago.

John and Catherine’s only son, John Stephen Gregory, was born in Sheboygan in December of 1855. It is unknown when and where John Gregory married Catherine Leonard. Since Creggan parish in County Armagh and Kilkerly parish in County Louth were extremely close to each other, it is not inconceivable that they met in Ireland.

By 1858, John Gregory was himself a resident of Chicago and resided at various addresses between Chicago and Division Streets in the now-called River North area from 1858 until the Fire in 1871. The 1866 through 1868 directories listed his home at 273 N. Franklin in the 19th ward which is confirmed by the 1870 US Census. The pre-Fire listings are:

1858 – Division n Larabee
1860 – 99 Larabee
1862 – SW corner Division and Franklin
1866 – 273 N. Franklin

John Gregory built over 25 ships in shipyards located in Wisconsin and Chicago. His last schooner, which was built in 1875, the Mary A. Gregory, became part of Chicago history, when she was the last commercial sail vessel to port in Chicago in the spring of 1924. The Chicago Historical Socoety has a permanent display of artifacts from her including the masthead and side lanterns.

After the Chicago Fire, John and Catherine Gregory moved from the destroyed North Division to the West Division of the city. They resided at 320 Hubbard Street (between Ada and Elizabeth Streets) until 1883 and then moved to 421 W. Ohio Street (between Ashland and Armour Streets), where they lived until their deaths in 1894. John and Catherine passed away only a couple of weeks from one another.

In 1874, John Gregory had granted permission for his 19-year old son, John Stephen, to marry Rebecca J. Hunter. John Stephen and Rebecca were married in Chicago on 30 Dec 1874. John Stephen was at that time a salesman for Goulds and Caldwell Manufacturing Company, a leading manufacturer of railroad equipment and pumps.

Immediately after their marriage, John Stephen and Rebecca moved to the new Chicago suburb of Englewood and by 1878 had built their new home at 5918 Arnold. When the City incorporated the Town of Lake in 1889, the street name was changed to LaSalle. It is very possible that this property was owned by the Gregory family until construction began on the Dan Ryan Expressway, which opened 12 Dec 1962. Currently, the east side of the 5900 block of LaSalle faces the expressway, which is unfortunate since 5918 was on the west side. A search on the building’s history is planned, but since the house was built before the town was annexed into Chicago, little hope in finding details is expected.
John Stephen and Rebecca Gregory were the parents of six children, although only three reached adulthood. Francis Gregory, born in 1876, was one of the first students to enroll in De La Salle Institute, which opened in 1889. Unfortunately, due to a fire (surprise!), the school has no early records to confirm his enrollment. Francis married Rose McCullough in 1917 and their family included five children. Francis is the third of four generations that are resting in historic Calvary Cemetery in Evanston, IL. His son, Francis, a Chicago Police sargent, was mentioned in the Bill Gleason non-fiction novel, The Liquid Cross of Skid Row, was laid to rest at Calvary in 2006.

Edward had nine children, of which at least two have emigrated to Chicago in the late 19th century. The first was James J. Gregory who recieved his naturalization on 14 Oct 1894 in Chicago. The same day he secured his marriage license to Winnifred Duffrey. This line remained in Chicago to this day, but no current descendant remains with the Gregory name. Margaret Gregory resided in Chicago with her husband James Carpenter. They had no children. His sister, Mary, may have been a godparent of John S. and Rebecca’s children, but there is no hard evidence to support this. She married Bernard Harvey and returned briefly to Ireland to marry. They were known to reside in Anaconda, Colorado in 1900.

If you are interested in seeing what Chicago looked like before the Great Fire of 1871, visit our sister site, Chicagology which has Ward Maps that when used in conjunction with Census websites (such as can be very helpful in locating misspelled names.