Steinbeck stops in Chicago to meet up with his wife but doesn’t detail his time there, noting that it would damage the story’s continuity. Just before leaving the city, he picks Charley up from the kennel, and although he’s clean and well-groomed, the dog seems upset at having been abandoned for so long. They continue the journey on small highways across the farmland of Illinois and into Wisconsin. He’s surprised by Wisconsin’s diverse landscape; the state’s huge dairy industry led him to imagine that it might be 100% fields of cows. He particularly likes the Wisconsin Dells, an alien landscape carved by glaciers during the Ice Age.

Upon entering Minnesota, Steinbeck gets lost again: Although he mapped out a scenic route with three crossings of the Mississippi River, he gets trapped on a gigantic highway outside the Twin Cities and misses the river entirely. He stops at a German restaurant, which he finds disgusting. There, he asks the staff for directions to Sauk City, Sinclair Lewis’s hometown. They make fun of him for getting lost, saying that it’s impossible to get lost in Minneapolis.

After a quick visit to Sauk City and some reminiscing about meeting Lewis as an old man, Steinbeck continues on to Fargo, North Dakota.