Originally Posted by gemac

To do a Platinum Challenge costs $150 plus flights. To do as a mileage run, look for flights to Europe in fare buckets that earn 1.0 Elite Qualifying Points per Elite Qualifying Mile. Some nice W fares have been available during the winters in past years. As an example, AA 92 departs ORD 12/29 at 7:20 PM, arrives DUB 12/30 at 8:30 AM, return AA 93 departs DUB 12/31 at 10:30 AM arrive ORD 12/31 at 12:55, cost $437.90 all-in, 7348 points. You also get one day in Ireland to go pub-hopping. From there, you could just wait and let your normal flying fill in the other 2652 points, or you could do another mileage run or two in the U.S.

You don't tell us how many short flights you do in a year, or whether you can put them all on AA and how much discretion you have in booking them. If you can originate in MKE, it would only take 15 round trips to get Platinum status. Cost from MKE will normally be less than or equal to cost from ORD, so the cost for this would be nothing, but you wouldn't get status as fast.

Which is better for you? You will have to answer that.