The only problem with the North Central service is that it only runs 4x/day, with no off-peak service. As I can see the downtown train platform from my office window, I do take it sometimes when the timing works out. It's a shame that they can't run it more often, but it's a service that's run on a heavy freight line (just like the Heritage line serving Lockport) and they can't squeeze out more frequencies.
From Winfield, you're pretty much stuck, at least for another 3-4 years. Continental Air Transport has not been interested in running coach services from a handful suburban pickup points the way that for example Massport does in Boston. But I think that a continued increase in gas prices over the next couple of years will provide that economies of scale that companies such as Omega and Van Galder find in serving Hammond and Rockford, respectively.
If you have PLENTY of time to kill and are travelling during the day, you can do this:
- Winfield UP Metra to Elmhurst
- Pace Bus from Elmhurst Metra station to Rosemont CTA station
- CTA train from Rosemont into O'Hare
The entire trip would take you about two hours, assuming that the Pace departures from Elmhurst were reasonably coordinated with the arrivals from Winfield.
The suburban taxi services are now all "taxi associations" and make their money off of the drivers, not us. Drivers rent equipment and pay for dispatch feed on a weekly basis (if I recall correctly, about two years ago it was $175/week), and drivers pay 10% to have the taxi service process credit card transactions and reimburse the drivers. The taxi services are not interested in making money on shared ride services.