Hi capun,
I agree with Annie that Heathrow is a crazy maze of bus routes, lines, shops, crowds, but in the end I have always found that I get where I'm going. I once made a connection in twenty minutes that required a bus ride, going through security again and all of those hassles. There was undoubtedly luck involved with the schedule of the buses, but we were whisked up to the front of the lines and passed through quickly. When we arrived at our gate, just as the door was closing, the personnel were able to scan our baggage claim check and tell us that our luggage had made it as well. Now that is amazing. My only point is that though it is not a relaxing experience to spend much time in Heathrow, IMO they are pretty darn efficient.
The one airport you mention that I would be careful with is Boston. I had a late arrival into Boston for my transatlantic flight and had to get to another terminal with very little time to spare. The airport bus was nowhere to be found, so I hopped on a car rental bus and explained my plight and the driver very nicely let me ride with him over to the international terminal.
I fly through O'Hare a lot. The distances between gates can be long, and the weather frequently disrupts things, but the layout is pretty good and there are lots of shops and decent places to grab a bite to eat. American and United have hubs there and both of those terminals are pretty comfortable. The Iberia flight to Madrid leaves from the American terminal (American doesn't fly to Madrid), so if you arrive in Chicago from California on American, you won't have to change terminals.
Coming into O'Hare from abroad is much easier and quicker than Dallas, in my experience. For some reason in Dallas, not only are the immigration lines usually enormous, but the line to get through customs after you pick up your bags moves much more slowly than in Chicago, where you are whisked right through.
Lots of choices, but in the end I guess the main advice I'd have is to make sure you have a good window between flights. The airlines will book you with a 40-45 minute connection sometimes and that has led to many headaches for me.
Buen camino, Laurie