BTW, it's $4 round trip, $2 one way. So Chicago is a little on the high end, but not at all abnormal.
Chicago's El infrastructure is certainly not representative of new construction. Much of it is -- as infrastructure goes -- pretty ancient. They started building it out 100 years ago, after all. I think New York and London have the same issues. Modern heavy rail/subway systems are much faster. The El in particular seems to be hard to maintain -- putting 20 ton cars on metal stilts is not very maintainable. Real upgrades take years of interrupted service, so that's not very feasible either. The result is a pretty slow train system. I think the Brown Line (one of the slowest) averages 15mph (including time at stations).
Chicago has crazy sprawl in the suburbs, but I'm not even considering them at this point -- there's still a very large urban area of Chicago of medium density that's not being well-served. I bring it up in part to shoot down another mass-transit-phile argument, that if you just had the right urban planning this would be easy. Chicago proper has planning that is amenable to mass transit, but it still doesn't work very well. We have a decent amount of bikers (by US standards) and lots of pedestrians, and lots of people that don't own cars. Everything other cities are trying to achieve. And it still doesn't work. There's no significant natural or manmade barriers to non-car traffic in the city, which is better than lots of places. But it still doesn't work. Box stores with parking lots in front have made up a sad amount of new development in Chicago, but most commercial space is still right on the sidewalk. We have 12k people per square mile. We have alleys, and we don't have many driveways crossing sidewalks. We have lots of one-way streets. Almost all our streets are multi-use -- shared and chaotic and cooperative. Chicago has most of the things that New Urbanists talk about. In a lot of ways Chicago is the best of a bad lot. But it still doesn't work!
Maybe if a city is just more clever it could work. Adding bike lanes on existing streets next to a parking lane doesn't make for a great bike lane. Building a less centralized set of trains would be better than the spokes we have. Public bathrooms downtown would be super. Sometimes the sidewalk is too narrow. Vehicle pollution is a real problem as a pedestrian; I wish we had better emission controls. Our parks, though generally well used, are mostly quite sterile, and others can be hard to get to, especially with public transit (since the nicer parks are on the edge of the city, and they aren't on the way to anything, so they get worse service).
But frankly I'm rather skeptical. I've heard lots of good things about Portland's planning and transit. But I still think we need something a bit more radical. I feel like a lot of the reaction against the suburbs is just reaction, just reactive, just trying to fight against something. I know what they are fighting for, too; but it's caught up in values and goals that can't be transferred, or are too hard to transfer, and too hard to get people to care about. But real functional improvements are much easier to express and convert people to than these vague values we have. The best planning isn't just pleasant, but it's inclusive and expansionist and functional and productive. Those are the defining attributes of America -- and the suburban style of planning has lived up to those things, as ugly and impersonal and wasteful as the result is.
See my reply below about radical changes. Portland did a lot of things right. If you haven't been there it's quite an enjoyable experience. Not just the transit, but the little parks downtown, Powell's books, etc. The transit is cheap. The MAX light rail goes east, west, and north into the suburbs (and would have gone to Vancouver WA if they hadn't voted it down). The east line was the first, unfortunately it has way too many stops. But they built it in open woods in Gresham where they wanted development to occur, rather than letting sprawl happen and then having to take out businesses for it. But many people I know live in southeast Portland which has no MAX, and you have to wait half an hour for a bus on Sundays. This even though it's an inner-city neighborhood close to downtown.
Seattle has a better bus system, more frequent, almost 24 hours to the inner neighborhoods and the airport, and almost as cheap. But it's only buses. So if there's a baseball/football/basketball game or just an everyday accident, you'll be sitting still for a while. They are building light rail, and we almost had a monorail too but it was cancelled. (Not the 60s monorail; I mean one that residents could actually use.) The regional organization that's building the light rail, Sound Transit, refused to consider monorail or PRT because "light rail is the only system proven in the US, so it's the only system we can get a federal grant for". The monorail advocates said screw the federal funding, we'll build it ourselves. It would have covered the west side, where light rail was not slated.
It sounds like you've read Jane Jacobs (The Death and Life of Great American Cities); she was the first New Urbanist if you want to call it that, and has many good ideas about making cities human-scale even though she was writing in the 50s. Basically, things have to be "small". There can be a lot of small things over a large area, but no huge housing developments or lonely big buildings. Chicago... is partway there, but still has more "bigness" than it needs. I think it was Clark Street between Belmont and Fullerton that I felt that, near some big block-long stores. And Fullerton near Orchard Street; things felt a little more spread out and residential than they had to be. (I don't believe in pure residential areas.) I don't know about Chicago parks, but Jacobs points out that parks in general must be laid out for the convenience of the park user, not built arbitrarily to look pretty. So many parks have empty benches... because they're not in places where people want to sit. People want to watch other people, so benches near other people get well used. Plazas get well used for the same reason. Does Chicago have any central plazas? Those are rare in the US, but they're the things that could make the biggest difference in making a city "comfortable" if done right. But they have to be close to people's houses or wherever they would normally be anyway.
Transit suffers from the same problem: you have to start with what the riders want. Speed, frequency, comprehensiveness. Most transit systems fail on all three counts. Cities don't build what transit riders want; they build the minimum necessary to get the advocates to shut up. Or they delude themselves that one light rail line will solve everybody's transit needs.# Mike Orr