Why do you think Chicago is such a good city? It's terribly spread out and inefficient, with mostly single-family homes. Compared to New York, which is dense with apartments even outside of Manhattan or directly on the east river, it's basically a suburb. I don't think a dense downtown attached to suburban sprawl is suddenly good urban planning just because the sprawl has a train going through it, you've just created commuter rail with a subway system instead of infrastructure to allow the city to exist outside of the small radius that zoning allows it to.
Okay so first have you ever been to Chicago? I ask this because from the way this ask is phrased I feel like you haven’t been there. Because yes there are very suburban sections in city limits but also Chicago has some of the most dense mixed use neighborhoods in the country and the L is not just there for commuters but it allows you to access shopping districts like Milwaukee Avenue or diverse neighborhoods like Chinatown, Uptown, Rogers Park, Pilsen, and Logan Square as well as many of Chicagos parks like Lincoln Park or Wicker Park. The reason I praise Chicago is because it much more similar to the typical American city than New York but still is incredibly walkable with a diversity of uses, a great parks system, and all around is one of my favorite places. Yes it does have flaws like the endless suburban sprawl but the city proper is a genuinely amazing place.