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Many would consider $200 (if that's round trip) to be an great price and be all over it.

One thing that may help (or may not, it depends) is to book the tickets as follows

Instead of booking a round trip on the same day, book your return (Chicago to New York on a Saturday evening) as the first leg of the trip, and the second leg would be the following Saturday to get you from New York Back to Chicago. It doesn't happen much anymore, but sometimes it may cut your fare.

Also look at pricing it as two one ways instead of a round trip.