Not sure about Chicago but in the Bay Area, you only get the cash back prompts when using a debit card, which also sets you up for additional fraud liability an

Not sure about Chicago but in the Bay Area, you only get the cash back prompts when using a debit card, which also sets you up for additional fraud liability and lower rewards kickbacks. I'd suggest getting a chase sapphire or citi DoubleCash card. It'll be faster as well (no idiotic cash back prompts with every transaction).