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Back in the day calling for a cab in Chicago if you lived close to the 'burbs was always a massive crap shoot. For a start, if someone tried to hail a cab on it's way to us, the driver would invariably take the hailer and leave us high and dry without our knowledge. Complaints got you nowhere.
Also, I used to live in the only part of Chicago (Montclare and Galewood) that did not have a 606xx zip code - it is 60707, shared with Elmwood Park. I'd call for a cab and the dispatcher would tell us (wrongly) we were in the 'burbs with that zip code and he can't send a cab. So then we'd call the suburban cab company which would then tell us that they couldn't do the job if the destination wasn't in the suburbs. What a pain.
Upshot - the unprofessional taxi cab industry in Chicago fully deserved to be eclipsed by rideshare apps.
Yes, you gotta feel bad for the individual taxi medallion owner.
BUT, when medallions are vacuumed up by speculators and , later, hedge funds - that's when the sympathy evaporates. All the speculators medallion market did was increase the cost of a cab ride, with zero benefit to both drivers and riders.
As a driver I always get suspicious if the pickup is a minor or a third party, and I will call the requester for clarification, which, certainly in the case of a minor, I will cancel.Also drivers never ever get a tip from such rides - reason alone to cancel.