I did quite a few DCA-ORD segments in my days living in Arlington, VA. I don't think a $195 R/T is all that bad. I would consider it unlikely that DCA fares would drop significantly lower. If you see a $149 e-saver, you'll still pay ~$175 when they throw the taxes on top. I'd take that $195 and see if either an AA discount code or a UA entertainment cert can make it a little cheaper, and book the flights you really want right now.

EDITED TO ADD: I just read the fine print on UA Entertainment, and those certs probably won't help much here. Minimum ticket $200, five percent discount from ORD.

The risk/reward in waiting isn't worth it if your goal is getting good flights in to DCA for a weekend in the city.

Also note that airlines usually consider MDW and ORD as equals when it comes to fare competition. (i.e., If Southwest drops a fare, UA or AA usually follow.) That helps you being in Wrigleyville - either airport is about the same in terms of convenience to you. However, in DC the airlines consider BWI a different beast from DCA. A Southwest sale won't cause DCA fares to drop.

[This message has been edited by pinniped (edited 02-07-2003).]