Chicago is both a landmark on Ish’s planned route across the continent and one of the expedition’s most revealing discoveries: a great city whose empty streets testify to the disappearance of its population. Its place in the journey joins Ish’s hope of finding other communities to the practical difficulties of travel through a landscape where roads are breaking apart and familiar urban scale has become hard to interpret.

A destination on the eastern route

Ish first imagines an eastward journey in terms of rivers, mountains, and roads. After the Colorado River, he expects the mountains to be manageable; the Rio Grande at Albuquerque would be the next major obstacle, followed by the Sandia Mountains and open plateau country. Farther east, travelers would have more roads to choose from. Beyond the Mississippi, however, the route becomes uncertain. Forest growth might have blocked the roads, though fires could have kept it down across parts of the old prairie country in Illinois. The expedition would have to go and see what remained, making decisions as conditions became clear.

When Ish later lays out a route for the boys, Chicago becomes one of a sequence of major cities to investigate. He sends them through Denver and Omaha to Chicago, then toward Washington and New York by whichever route proves most passable. He expects they will reach the city in spring. The plan is not simply a journey between known settlements: Ish wants the travelers to find communities and learn how other groups are managing and beginning again. Chicago therefore represents both a geographic waypoint and a possible answer to the question of whether organized human life has survived elsewhere.

The city encountered

The boys reach Chicago after crossing what was once Iowa and coming to the continent’s greatest river. Its bridge is still sound, an important contrast with the damaged roads elsewhere on their journey. The city itself offers no comparable sign of preservation in human life. Chicago is described as a desert of empty streets, not as a functioning center or a community waiting to be contacted.

Ish considers what the city would be like when winter winds swept in from Lake Michigan. He is not surprised that people, with a continent to choose from, had drifted away from the once-great city by the lake. That explanation is Ish’s inference from the emptiness, rather than a report of people the boys encountered leaving. The phrase ghost-like captures the difference between Chicago’s former scale and its present condition: the streets and buildings remain as evidence of the city, but the population that made it a city is absent.

Roads, growth, and disorientation

The approach to Chicago makes the surviving highway network feel increasingly unreliable. In the wetter country, heavy rains and hard winter frosts have worked on cracked surfaces until the highways split into great blocks and chunks. Grass and weeds, then bushes and young trees, grow through the breaks and obstruct passage. The expedition’s difficulty is not only that a road may be physically blocked; the landscape is gradually obscuring the infrastructure that once made long-distance travel routine.

Chicago’s outskirts present a different obstacle. After leaving the city, the boys lose themselves in the maze of roads. On a cloudy day, with no clear sense of direction, they travel south instead of east. Their mistake shows how a dense network of streets and roads can become confusing when the systems and shared knowledge that once gave it meaning are gone. They obtain a compass from a store, and Robert has to look to Ish for the word for it. The small exchange links a practical tool to a larger loss: the expedition must recover both ways of navigating and the language for describing them.

What Chicago means to the expedition

Chicago does not deliver the community Ish hopes the boys will find. Instead, it gives them a concrete example of the difference between the survival of built structures and the survival of social life. A bridge can remain in good condition, and streets can still be traced, while the city they once served has become empty. The expedition’s discovery does not establish what happened to every resident; it leaves Ish to interpret the absence through the scale of the continent and the likelihood that people moved elsewhere.

The city also marks a limit to Ish’s ability to direct the journey from home. He can propose cities and routes, and he can judge what the boys should seek, but he leaves the return route to their choice because they will know more about conditions than he does. Chicago thus sits at the intersection of a planned map and an unpredictable world: a named destination whose empty streets, broken approaches, and confusing outskirts force the travelers to adjust their expectations and find their own way onward.