Chicago has its good and bad because of the people who define it. In the poem "Chicago", Sandburg is able to identify the existence of both good and bad in the city of Chicago because of his reliability, his descriptions of the Chicagoans, and the way he structures the poem. Sandburg's portrayal of Chicago is effective because of the realistic and reliable view that is used in this poem. He acknowledges that though a lot of admirable, hard work is done in Chicago, bad things happen too. In the second stanza, Sandburg admits that there are "painted women under the gas lamps luring the farm boys" (Sandburg, 85, 6-8) and "[gunmen killing] and [going] free to kill again" (85, 9-10). He doesn't deny that these repellent events take place in Chicago; he confirms that they do and that he has seen them happen. It is made clear that Sandburg has a deep love for Chicago by how he follows his recognition of the bad, "Come and show me another city with lifted head singing so proud to be alive and coarse and strong and cunning" (85, 15-16). His readers are assured of his reliability because of the frank manner in which he recognizes not only the good aspects of Chicago, but the bad too. It's no secret that he is proud to be a Chicago native, but he is also willing to admit that there are some "wicked," "crooked," and "brutal" (85, 6, 9, and 11) things that happen in Chicago, which gives him credibility. .
Sandburg's most used method of describing Chicago is describing the Chicagoans. He says that Chicagoans can be found "bragging" (86, 32) to explain that yes, the people of Chicago are human and have sides to them that may not be very admirable but offers many commendable verbs as well. These words of action, "Shoveling," "Wrecking," and many others help to illustrate the point that Chicago is a city of activity and hard work (85, 22-23).