Friday's Journey. It just happened to be set in the city, too.
In Ken Rush's Friday's Journey, Chris' parents are divorced and his dad has come to pick him up for their Friday journey, which is a subway ride to Dad's place, where he spends the weekend. During the train ride, Chris imagines the places the train could take him: places he used to go with both his parents. In the end, he realizes he can still enjoy those places just with Dad.
The story fell a little short for me, but I imagine it has a place among the targeted audience. However, there are a number of specific subway experiences that my young listeners grabbed on to, which is why I'm including a review on this blog. For example: the distant lights of the subway in the tunnel, the experience of watching the tracks out the front window, the screeching noise of the train stopping in the station. The city is obviously New York City, but it is never mentioned by name and because of the book's theme of living with divorced parents this book will find an audience outside the local one.
My favorite book about a dad and his sons riding the subway is the ingenious Subway
by Christopher Niemann.
Little Kid says: Where is that train going?