Wright arrives in Chicago and Works for Joseph Lyman Silsbee

In 1887, Wright arrived in Chicago in search of employment.

Resulting from the devastating Great Chicago Fire of 1871 and recent population boom, new development was plentiful in the city. He later recalled that his first impressions of Chicago were that of grimy neighborhoods, crowded streets and disappointing architecture, yet he was determined to find work. Within days, and after interviews with several prominent firms, he was hired as a draftsman with the architectural firm of Joseph Lyman Silsbee. Wright previously collaborated with Silsbee — accredited as the draftsman and the construction supervisor — on the 1886 Unity Chapel for Wright’s family in Spring Green, Wisconsin. While with the firm, he also worked on two other family projects: the All Souls Church in Chicago for uncle, Jenkin Lloyd Jones, and the Hillside Home School I in Spring Green for two of his aunts. Other draftsmen that also worked for Silsbee in 1887 included future architects, Cecil Corwin, George W. Maher, and George G. Elmslie. Wright soon befriended Corwin, with whom he lived until he found a permanent home.

In his autobiography, Wright accounts that he also had a short stint in another Chicago architecture office. Feeling that he was underpaid for the quality of his work for Silsbee (at $8.00 a week), the young draftsman quit and found work as a designer at the firm of Beers, Clay, and Dutton. However, Wright soon realized that he was not ready to handle building design by himself; he left his new job to return to Joseph Silsbee – this time with a raise in salary.

Although Silsbee adhered mainly to Victorian and revivalist architecture, Wright found his work to be more "gracefully picturesque" than the other "brutalities" of the period. Still, Wright aspired for more progressive work. After less than a year had passed in Silsbee’s office, Wright learned that Adler & Sullivan, the forerunning firm in Chicago, were "looking for someone to make the finish drawings for the interior of the Auditorium [Building]." Wright demonstrated that he was a competent impressionist of Louis Sullivan’s ornamental designs and two short interviews later, was an official apprentice in the firm.

Yearning to go to Chicago, Wright pawned some of his father’s books in 1887 and used the money to buy a ticket on the next train to Chicago. On his fourth day in Chicago he walked into the office of Joseph Lyman Silsbee, an architect who had been associated with the Jones family, and after being interviewed by Cecil Corwin, one of the draftsman in Silsbee’s office, he obtained a job as a tracer for eight dollars a week.

Wright worked for Silsbee for about a year before he left to take a better paying drafting job with Louis Sullivan and Dankmar Adler, who were working on the design of the Auditorium Theater in Chicago at the time. Wright referred to Sullivan as his Lieber Meister (beloved master) and was the only architect that Wright would acknowledge had an influence on him. The basis for Wright’s future work was born out of the idea and philosophy of Sullivan’s that "form follows function".