Others may have no problem with the Chicago Card but when I switched from my 30 day pass I had nothing but trouble: (1) the card short changed me 3 times--mysteriously cutting off short of a full month (ones of 30 days) and even though they restored the lost $$, they did so days after I needed to use the card so I had to always remember to carry a regular card with $$ on it; (2) in a month of 31 days I had to use the regular card since the Chicago Card didn't kick in on a 30-day cycle--however they did take my money 2 weeks before the new start date; (3) when I tried to get some help from the CTA office that handles these things I got zip (well that's not the card's fault I suppose, that's just the CTA!) So I gave up and now get my 30-day pass from work (pre-tax) and always have another ready to go--no problems, ho hassles.
Chicago Cards--NO WAY!