Marriage #1: Juliette Morton

Married: 5 May 1838

Death: 29 May 1853

Children:

1. Olive Churchill b: 20 Apr 1839 in Lombard (Du Page) Illinois
2. Orson Churchill b: 12 Jun 1840 in Lombard (Du Page) Illinois
3. Orscena Churchill b: 16 Jan 1842 in Lombard (Du Page) Illinois
4. Esther Churchill b: 12 Jul 1844 in Lombard (Du Page) Illinois
5. Philindia Churchill b: 4 Jul 1846 in Lombard (Du Page) Illinois
6. Harriet Churchill b: 28 May 1849 in Lombard (Du Page) Illinois
7. Elvira Churchill b: 8 Mar 1850 in Illinois
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Marriage #2: Sarah A Nichols

Married: 10 Nov 1853 in Glen Ellyn (Du Page) Illinois

Death: 25 Oct 1858

Children:

1. Henry W Churchill b: 22 Nov 1854 in Lombard (Du Page) Illinois
2. James W Churchill b: 23 Sep 1856 in Lombard (Du Page) Illinois
3. Issac B Churchill b: 24 Oct 1858 in Lombard (Du Page) Illinois
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Marriage #3: Margaret Willard

Married: 25 Dec 1858 in Du Page County Illinois

Death: 1 Nov 1882

Children:

1. Orilla Churchill b: 27 Oct 1859 in Lombard (Du Page) Illinois
2. Rozella (nee Churchill) Lacey b: 27 Oct 1859 in Lombard and died 28 May 1928 in Downers Grove (60272865)
3. Annise Churchill b: 3 Oct 1862 in Lombard (Du Page) Illinois
4. Louisa Clarise Churchill b: 25 Dec 1864 in Lombard (Du Page) Illinois
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Marriage #4: Mrs. Elizabeth Evans

Married: 4 Jun 1895 in Du Page County Illinois
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The following article is from "Portrait and Biographical Records of Leaders of Cook County and DuPage County."

"Winslow Churchill, a retired farmer now living in Downer's Grove, is one of the self-made men of this community, who
by his own efforts has risen from a humble position in life to one of affluence. The record of his career, which we feel assured will prove of interest to many of our readers, is as follows: A native of the Empire State, he was born June 13, 1813, in Onondaga County, and is one of a family of twelve children, numbering five sons and seven daughters, whose parents were Winslow and Mercy (Dodge) Churchill. The former was a native of Vermont and in his earlier years followed the mason's trade, but later in life became a farmer. The members of the family who are now living are: Christina, wife of James Christian, who makes her home near Prospect Park, in her ninety-second year; Betsy, who is living in Cook County, in her eighty-sixth year; Winslow, who is the next younger; and Bradford, a farmer living near Lombard. Mr. Churchill of this sketch was reared to manhood in the usual manner of familiar lads, and in his youth received very limited school privileges. In 1834 he came with his father to DuPage County, the family locating near Lombard on a claim of between two and three hundred acres, on which a log cabin was built. For about three years our subject continued at home and then entered a claim of his own from the Government of one hundred and sixty acres, purchasing the same when the land came into market. It was in its primitive condition, but with characteristic energy he began to clear and improve it, and there continued his fanning operations until 1868. In that year he removed to Lisle Township, where he made his home until 1879, when he came to Downer's Grove. Since that time he has lived retired. Mr. Churchill made the trip westward on a sailing-vessel on the Great Lakes, reaching Chicago only after five weeks from the time when he left Buffalo. Chicago was his nearest trading post, and to that place he hauled his grain and other farm products. There was only one log cabin in Lombard, and much of the land of the county was still in the possession of the Government. Mr. Churchill truly deserves to be numbered among the pioneer settlers, and also among the founders of the county, for he has ever borne his part in the work of public improvement and development. Mr. Churchill has been three times married. He first married Juliet Morton, and unto them were born the following children: OUie; Orson,
deceased; Lucinda; Esther and Melinda, both of whom are deceased; Harriet and Laura. The mother of this family died May 29, 1853, and on the 10th of November, 1853, Mr. Churchill married Sarah A. Nichols, by whom he had three sons: Henry, James and Isaac. The second wife died October 5, 1858, and he was married to Miss Mariette Willard on Christmas following. The children of this marriage, four in number, are Orrila and Roella. twins; and Anna H. and Louisa. The mother's death occurred on the 1st of November, 1892. Mr. Churchill cast his first vote for John Calhoun, and was a supporter of the Whig party until its dissolution, when he joined the ranks of the new Republican party, and has since upheld its banner. His time and energies throughout life have been devoted to farm work, and through industrious, perseverance and good management his career has been a successful one and he has accumulated a comfortable competence."
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"Winslow Churchill Jr. Born in New York he was one of 12 children of Winslow and Mercy Dodge Churchill. The family moved to DuPage County in 1834 and settled in what is now Lombard. Winslow Sr. bought several hundred acres of land there for his large family. Winslow Jr. bought his own land in 1837 when he was 25 and operated his farm in the area until the 1860ʼs when he moved to Lisle and bought several hundred acres of land there. Here he engaged in farming
selling his grain in Chicago and worked for the improvement of the county. Winslow was married 4 times and had 11 children. By 1879 when he was 67 he retired from farming and went to live in the Village of Downers Grove. Winslow Jr was a true pioneer of the county making his home here when the county was first beginning. He died in his Downers Grove home at the age of 87 and is buried in Oak Hill Cemetery with his 3rd. wife Mariette Willard who died in 1892."

-- From the Dupage County Genealogical Society NOVEMBER 2013, VOLUME #5 ISSUE #6 Newsletter.