When we were in Chicago, we used to go to the tourney in Indianapolis (which has now relocated to Atlanta). We could get 2nd or 3rd row baseline tickets for ~$40 midweek. Saw Roddick play there which was fun as he had a running conversation with the people close by. We went to the US Open a few years back, and I believe we spent greater than $150 each for nosebleed tickets to an early round (to see, oddly enough, Roddick, who we also saw in Indian Wells & Cincinnati.) The best deal in tennis is grounds passes at Wimbledon which were £15 when we went. We shared a courtside bench with Chakvetadze's dad and coach and then got courtside Centre Court seats to see Bartoli (who was the defending finalist) for £5 (as people leave early, they resell the tickets for charity).