Born in Virginia, a member of the prestigious Barbour family on his mother's side, Bryan largely made a name for himself in Chicago, Illinois.

Bryan also played a key role in the development of the Chicago suburb of Elmhurst, Illinois, where he resided much of his life.

He would, soon after graduating, publish grammar meant to help Germans learn to read, write, and speak the English language.

[24][23][25] Their adult son was Charles Page Bryan, born in 1855, who would have a career as a lawyer, politician, and diplomat.

[5] Shortly after living here, he built a house at the northwest corner of Wabash Avenue and Jackson Street.

[17] Sometime between 1856 and 1859, Bryan settled in Cottage Hill, Illinois (modern-day Elmhurst), building a 1,000-acre estate there named "Byrd's Nest".

Healy would be a lifelong friend,[30] and in 1857 bought the Hill Cottage from Barbour to serve as a residence for his own family, making them neighbors.

[31] Once completed, the Byrd's Nest estate included a 21 room manor, a separate garden house, and a man-made lake.

[28] In the 1860 United States census, Bryan was recorded to be the wealthiest person in DuPage County, with a net worth said to exceed $325,000.

[28] In 1864, he would sell 26 acres of his land to his brother-in-law Jedediah Hyde Lathrop, who built his own estate named "Huntington" on the site.

The 1865 Byrd's Nest chapel stood where the intersection of Cottage Hill Avenue and St. Charles Road is today.

[30] In 1869, Bryan assembled a number of Cottage Hill residents and proposed the idea of renaming the community to "Elmhurst", a name reflective of the German heritage of many town residents and the many elm trees that Bryan had planted across the community over the course of the preceding ten years.

[30] That same year, Bryan and his wife Jennie sold 30 acres of their land in Elmhurst to the German Evangelical Synod of the Northwest for $10,000.

[30][33] In 1860, Bryan established Chicago's Graceland Cemetery in partnership with William Butler Ogden, Sidney Sawyer, Edwin H. Sheldon, and George Peter Alexander Healy.

[23] In April 1860,[23] the first burial at Graceland Cemetery occurred when Bryan had his late son Daniel reinterred there.

[4] He did not desire to be mayor of the city, nor did he want to cause disarray or fractures in the Republican Party at the time that the Civil War was beginning.

[4] Bryan was the National Union (Republican) nominee for the office in 1863, losing by an incredibly narrow margin to incumbent mayor Francis Cornwall Sherman.

[4][38] In his first campaign speech of his 1863 effort, Bryan remarked that while he had not sought nomination, he would accept it in consideration of the cause of union amid the American Civil War, declaring agreement with the platform of the ticket he was nominated on, The Union men I conceive to stand pledged to a hearty support of the Government in its efforts to suppress the accursed rebellion.

[3][5][17] He was also president of the Northwestern Sanitary Fair, an event held in 1865 along the Chicago lakefront which raised more than $300,000 for Union soldiers.

[3][5][17][41][42] Interestingly, his wife had incidentally been in the company of Confederate Army general Robert E. Lee, a relative of hers by marriage, just days before the breakout of the Civil War.

[45] He purchased the metal from the Chicago Court House Bell which he used to fashion an alarm for his company, selling the rest to H.S.

[21] At the time of the 1880 United States census, he was recorded as residing in Clear Creek County, Colorado.

[22] In 1890, he, alongside Chicago mayor DeWitt Clinton Cregier and former Illinois Central Railroad president Edward Turner Jeffery, gave the presentation for Chicago's bid to the fifteen member United States Senate committee that decided what location would be awarded the fair.

[17][48] After Chicago landed the fair, Bryan was appointed a commissioner-at-large of the World's Columbian Exposition Board created by federal legislation.

[28][50][51] Bryan worked successfully to convince the Chicago City Council, Illinois General Assembly and United States legislature to pass legislation providing assistance to the fair's organizers.

[5] At the same time that he was organizing the world's exposition, Bryan fell victim to what ultimately turned out to be a scam run by H. H. Holmes, a man who was later discovered to be a serial killer.

He lost more than $9,000 after becoming involved in a copier machine business with Holmes at the advice Bryan's associate Fred Nind.

[34][50] Bryan was widowed on March 5, 1898, when his wife of 48 years, Jennie, died at the age of 68 at their Byrd's Nest estate of paralysis that had impacted her brain and vocal organs, before reaching her heart.

After the Great Chicago Fire, Bryan purchased the broken remains of the bell from the city's lost courthouse at an auction.

[68] After notable people had been invited to send items to the Northwestern Sanitary Fair to auction, Abraham Lincoln sent the original handwritten draft of the Emancipation Proclamation.