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I don't know about cabbie's contracts, but Uber offers this as an option (including in Chicago).

https://www.uber.com/chicago-drivers/services/uberCAB/

As a customer, I've only done it because I wanted a cab after a concert and didn't want to wait in line -- I walked two blocks and used Uber to hail a cab instead.

You pay meter fare plus tip and the whole thing is charged through the app.



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