After a series of reorganizations and expansions, Donnelley built the Lakeside Press Building on Plymouth Court, and in 1902 began construction of the R.R.

The company aimed to produce books and periodicals with impressive modern design and mass printed commercial and reference materials.

Donnelley was the official printer for the 1933–1934 World's Fair, "A Century of Progress", which took place on the Lake Michigan lakefront just to the east of the plant.

Donnelley's cartographic production facility grew to be one of the largest custom mapmaking companies in the United States.

In the early 1990s, the division successfully integrated routing technology with its digital map databases and launched a separate company, Geosystems,[11] which several years later became MapQuest.

Donnelley's handling of the closing generated a lawsuit, which went all the way to the US Supreme Court, concerning alleged discrimination against black employees.

Donnelley, a Yale graduate and a trustee of the University of Chicago, felt that the recent revival of the ancient practice of apprenticeship was unsatisfactory because unions dominated the rules.

As Chicago became home to a northward migration of blacks, the workforce became stratified as non-whites found it hard to attain management positions.

Racial tensions in the 1960s further weakened the company's ability to meet technological challenges and global competition.

C. G. Littell, vice president and treasurer, and William A. Kittredge, head of the department of design and typography, organized the campaign.

[20] The best known of the publications in the series was Rockwell Kent's edition of Herman Melville's novel, Moby-Dick, which at that point was not yet accepted as an American classic.

Kittredge commissioned Kent to perform the design and illustrations in 1926, and the book appeared four years later in a three-volume limited edition of one-thousand copies issued in an aluminum slipcase.

The character of the type should be homely, rather than refined and elegant, for homeliness flavors every line that Melville wrote."

[24] In 1929, the company opened the Lakeside Galleries on the eighth floor of their newly completed building on 22nd Street.

From 1930 to 1961, when the corporate headquarters were moved, the galleries devoted exhibitions to the works of American and European artists and photographers, as well as to typography and book design.

Donnelley also acquired book and educational materials printer Von Hoffmann (and creative/ pre-press subsidiary Anthology Inc.) from Visant Corporation.

Donnelley also purchased Perry Judd's Holdings Inc., a private catalog and magazine printer, at the beginning of 2007.

[29] In 2005, it acquired Hong Kong based Asia Printers Group from CVC Capital Partners.

[31] In 2006, it acquired Canadian Bank Note Company's financial printing business, consisting of documentation for initial public offerings.

Donnelley announced that it had entered into a definitive agreement to be acquired by Chatham Asset Management for $7.50 per share in cash.

Donnelley Company produced fine-quality books as well as mail order catalogs, telephone directories, encyclopedias, and advertising.

The Press was best known for its high quality editions for the Chicago Caxton Club as well as the Lakeside Classics, a series of fine reprints produced annually, at Christmas time, by R.R.

The basic format of these books has remained essentially the same since inception, as a hardcover, cloth wrapped and gold embossed.

Many early volumes contained speeches and writings of noted Americans, including Benjamin Franklin, whose autobiography was published as the first Lakeside Classic.

[53][54] Thomas Donnelley wrote in the introduction to Autobiography of Benjamin Franklin, the first volume in the series, that "If, in a modest way this volume conveys the idea that machine-made books are not a crime against art, and that books may be plain but good, and good though not costly, its mission has been accomplished."

The Chicago publisher Reilly & Britton was given rights to reissue some of the earliest titles as “The Patriotic Classics.”[52] By 2015, the series included 113 volumes.

Antiquarian bookstores often have a section devoted to Lakeside Classics, and early volumes command large sums from book collectors.