There's a difference between airport taxi service by chauffeur-licensed drivers dispatched by a branded cab company (with something to lose if drivers misbehave) and "I signed up with 1 of 5 different companies that dispatch cabs with iPhones".
I don't have prove that the Chicago medallion system is sensible; I'm only objecting to the notion that there is no valid concern behind them other than for-profit restraint of trade. There are absolutely valid concerns behind medallions. Go to an NYC airport or outside Penn Station and find an unlicensed cab; take 10 drives, and tell me how many of them try to screw you over. Do the same thing with medallion drivers; none of them will.
However, I had much more experience with unlicensed cabs in Washington Heights (north end of Manhattan, where licensed cabs refuse to cruise around to get business) and I never remember anyone trying to rip me off. Much of the time this wasn't with calling any specific company, just flagging down (illegally) whichever car was passing.
I think there's just too much money to be made from unsuspecting tourists at NYC airports.
For example, cabs could earn (and risk losing) a "Good Cabdriving Seal". There's no need for the quantity of such seals to be artificially limited: they could be unlimited, but only awarded to those that prove worthy.
And while we're at it, the agency doing the certification need not be a government agency at all. Why not Good Housekeeping, or Underwriters Laboratories, or Better Business Bureau?
The medaillion system is weird, but it works in new york.
The people who think that the invisible hand of the market would improve cab service are awesomely naive. The reason why cabs aren't fucked up in NYC is because of all the regulations, which can only be enforced because the cabbies have something to lose (the mediallion). If there was no government interference, cabs still wouldn't take credit cards, they wouldn't pick up non-white people, they wouldn't drive you to Brooklyn, they would form their own cabal and eventually rip out their meters and just make up whatever price they wanted to charge you, once you got there.