This is illegal. Suburban taxis aren't allowed to collect fares in the city and then deposit them in the city limits.

That aside, I have had good luck with the Chicago Carriage cab folks - the maroon ones. They are always timely when I call and always get my rollaboard into and out of the trunk.

I usually give the cabby the cue he's getting my bag out for me by transacting business outside the cab - he gets paid in back by the trunk unless I want to hassle with the credit card. I did the credit card thing for a while but it completely messes with my expense reports so I just stopped doing it and carry cash for it and besides it saves the whole hassle of "the machine is broken".