Daniel R. Hundley kept a diary while he was in Chicago seeking a career as an author. The diary contains daily records of his activities and his reactions as a southern Baptist, living in the North, to national and international political issues such as abolition. He wrote of current political and social events and of his deepening poverty. Interspersed with the political commentary are notes on the progress of Hundley's sick wife, whose condition he described almost daily. Hundley was not employed, but often went into the city, sold produce from the farm, and was an avid hunter of small game, especially passenger pigeons, quail, and rabbits. Throughout the year, Hundley worked on writing a book to explain the South and slavery to northerners. This volume was eventually published in 1860 as Social Relations In Our Southern States . Chapter titles include: "Southern Yeoman," "Middle Classes in the South," "Southern Bully," "Cotton Snobs," and "Negro Slavery in the South." He occasionally sent philosophical essays to The Harbinger and to Harper’s Weekly, but they were rejected for publication. Though not a secessionist, he was strongly pro-slavery, which caused some friction with his northern neighbors. Finally he sent his wife and children off to live with his father in Alabama and left for New York to study for the ministry.
- January 1: Hundley listed his debts and assets and voiced approval for Senator Stephen Douglas over Senate candidate Abraham Lincoln.
- January 30: Hundley discussed reading Livingston’s "Travels in Africa" and points out abolitionists' inconsistencies.
- February 5: Hundley recorded that his wife’s grandmother died in Virginia, leaving 17 family servants to her and her other grandchildren. The relatives in Virginia wanted to pay Hundley's wife for her share of the slaves, so that they would not have to be sold.
- February 27: Hundley reported that some Chicagoans had contributed $10,000 to purchase Mount Vernon from a relative of George Washington.
- February 28: Hundley wrote that General Daniel Sickles had shot and killed United States Attorney for the District of Columbia Philip Barton Keys for having an affair with Sickles's wife.
- April 21: Hundley heard Henry Ward Beecher lecture and concluded that he was only a second-rate man with little grasp of intellect or depth of thought: "His forte is neither reason nor common sense."
- July 1: Hundley wrote that Napoleon III’s Franco-Austrian war had depressed grain prices and that he wanted to buy some wheat on speculation. However, the depression in the grain market had caused some of the most prominent grain dealers in Chicago to fail.
- October 18: Hundley learned of John Brown's raid on Harper's Ferry. He referred to Brown as a "crimson sinner," and called for his life as punishment for the raid.
- October 20: Hundley revealed his happiness at the deaths of Brown's sons: they lie "stark dead upon the sail of Slavery."
- October 22: Hundley incorrectly assumed that Harper's Ferry would "prove the death-blow of [the Republican] party, and will force them to abandon their separate organization and unite with the general position."
- October 27: Hundley mentioned that an "ultra Republican [...] believed Brown would be canonized as a martyr for Liberty in one hundred years from to-day."
- October 29: Hundley reported that William H. Seward was implicated in "the sad affair of Harper's Ferry," and Hundley predicted the end of Seward's political career.
- November 2: Hundley wrote of Brown’s conviction.
- December 1: Hundley worried about the "imminent dissolution of the Union." He argued with an abolitionist that the Bible sanctioned slavery.
- December 2:, Hundley expressed his hope that the Union would be saved and that Brown's actions would not cause it to rupture.
- December 21: his brother arrived from Alabama with $2,000, which enabled him to pay off his creditors. He put his wife, his three young children, and a servant on a train for Alabama and set off for New York City for the winter, where he planned to enroll in a seminary and study to become a Baptist minister.