Also, are you controlling for the housing type? Condos in high rises (which are much more expensive than detached single family detached) tend to be concentrated near the trains.
Ive consistently had it take an hour to move ten miles regardless of the day of week to visit family in Milwaukee. At least a third of the drive I could see the Sears tower in the rear view mirror. Amtrak/metra is far superior to car ownership. Uber for local travel and is quite frankly cheaper with less aggravation because I don't have to deal with it. apparently honking your horn and not using a blinker is standard. Also just generally driving like a complete asshole. And don't get me started on the taxis. That entire industry in Chicago should go out of business. And cyclists seem to vary. Some are very respectful and will quickly stop for a j walker and politely say they shouldn't do that. Others run red lights and get pissed when you call them out for riding on the sidewalk.
Some startup should come with a device that is required for Chicago drivers... every time you honk your horn it costs 5-50 dollars. What are you fucking honking for there is 25-100 cars ahead of you not moving.
These sorts of land desirability drop-offs happen very quickly in Chicago, but that could just be a function of density. Commutes in Chicagoland aren't necessarily any worse (in terms of commuting time) than they are in other places I've been - you just end up with the pattern spreading over a much wider geographic area because cars spread everything out so much.
For example, Milwaukee's rough equivalent of Chicago's West Rogers Park is probably Menomonee Falls, which isn't even in the same county. But you've got a similar pattern where it's kind of off the beaten path, transportation-wise, which makes it relatively inexpensive compared to a more well-connected area like Tosa or Whitefish Bay.
I've noticed similar patterns in North Carolina, too - plenty of people I know in the Triangle have commutes that are well over an hour, and the communities from which it's easy to get to the major employers command a premium.
If anything, I feel like this is more argument about Chicago needing a less hub-and-spoke design to its rail transit. Out on the periphery, it's possible to get very far away from the rail lines. In a city this size, it's a major failing that anyone ends up living more than 2 miles away from rapid transit.
This would lead to even more Uber/Lyft drivers which already make traffic considerably worse in my experience.
I would not drive to work just because the train isn't within walking distance, because, yeah, not worth the time and stress and expense. Having to take a bus or ride a bike to get to the nearest train station doesn't add that much time to a commute.
There's so many factors that it's hard to make direct comparisons, but for example you can look at homes near the Irving Park blue line stop (which also next to a Metra stop) and then similar home just a few miles West where there are fewer transit options. It's a pretty drastic drop off in home prices for relatively comparable neighborhoods.