Originally Posted by WearyBizTrvlr

Depending on what your priorities are, you could optimize the routing of your American segments to gain more miles. For instance, the Florida to NYC market is one of the most competitive in the US with a huge number of daily flights, so you could probably get a separate cheap TPA-NYC ticket (or go via MCO if you have the flexibility) and use the freed segment instead for a mileage run.

If you're only using ORD to connect to TPA, you could fly SFO-JFK instead and get a cheap return to Florida from there. You could also consider doing NYC-WAS separately, for instance by taking the Acela train.