Wow! Thanks for all the detailed responses! I'll have to reread them at home to really absorb some of them, but seems like there is a lot of good info in there.

Here are some more details on my situation:

"Relevant" Credit Cards
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AMEX Starwood Preferred Guest
AT&T Universal Cash Rewards Card (5% cash back on ALL purchases so that takes priority while that promotion lasts)

Significant Amounts of "Miles In Waiting"
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4,000 Starwood bonus points for first purchase
10,000 AAdvantage miles for AT&T long distance
2,000 Mileage Plus miles for linking account to Safeway shopping card (may only be available locally)


I use MyPoints extensively but find that the reward ratios are best for some things other than HHonors points (e.g. gift certificates to restaurants). I do use eRewards and am about to hit the $50 mark and grab 3,000 HHonors points. My decision on which shopping portal to use is based on return. Sometimes a shopping portal such as MyPoints will offer a better return than the airline shopping portals.

Multiple people have commented that I shouldn't use an award ticket for BWI-MDW because those flights are cheap. Two counterpoints:
- I will probably get that ticket at the last minute as I'm not 100% sure of my plans. Since WN lets you reserve any seat that's open it will work for me. The cheap rates on WN are already gone for the weekend of interest to me.
- Flying cross country on SW may be the best financial use of an award ticket, but it's not one that sounds super appealing to me. I find their planes to be tight in terms of space and the atmosphere less professional than the majors.

So I'm still considering using an award ticket for BWI-MDW. Feel free to try harder to convince me not to.

Back to work...