When will Cook County expect 2nd property tax payment? The second installment of Cook County property taxes should have been paid Aug. 1. Cook County residents were supposed to pay their second property tax installments on Aug. 1, but the county hasn’t been able to calculate the final amounts and billions worth of tax bills haven’t been mailed. Illinois Policy Institute research shows Cook County property tax bills have risen 78% since 2007, despite median property values rising just 7.3%. That 4% increase marked at least the 30th year Cook County property taxes have increased.