As someone whose parents shelled out as much as a trans-Atlantic plane ticket costs to make sure I got home for Christmas, I'm not sure how much advice I'd have about cheap fares. Usually we do pretty well, but this year has been strange. Hotwire and Priceline are pretty safe bets. I've gotten tickets on Hotwire with less than a week before the flight for about $200 (from Northern Florida to STL). I know Southwest flies between Chicago and STL, you could possibly call the airline and see how much a flight would cost (sometimes they have very very very cheap flights left). I can't imagine paying more than $150 between STL and Chicago, but maybe that's just me.
Good luck!
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