During the 1860s, Chicago was considered the center of the wholesale dry-goods trade. In 1865, Ward found his way to Chicago and began work as a traveling salesman for Case & Sobin, a lamp house. Later, Ward joined Field, Palmer, and Leiter, forerunner of Marshall Field & Co. He worked under Field for two years and then joined the wholesale dry-goods business of Wills, Greg & Co. (37)

As a salesman, Ward traveled far and wide to various communities. He observed and listened to the complaints of his rural customers and realized he could offer them better prices by selling to them directly, via mail-order, a revolutionary new concept. At the time, rural customers longed for the retail comfort of the city. They faced stiff costs of goods as a result of the many middlemen required to bring manufacture goods to the countryside. Although many considered Ward's idea to be insane, he continued with his business plan. (38)

"Although today the Sears Tower in Chicago is the world's tallest building, there was a time when Montgomery Ward's headquarters was similarly distinguished. The Montgomery Ward Tower, on the corner of Michigan Avenue and Madison Street in Chicago, reigned as a major tourist attraction in the early 1900s. Aaron Montgomery Ward, who was called "one of the nation's first environmentalists," said that he "fought for the poor people of Chicago, not for the millionaires." (39)

On December 7, 1913, Aaron Montgomery Ward died at the age of 69. A significant portion of his estate was left to Northwestern University and other educational institutions by his wife. (40)