For travel over the Labor Day holiday, fly nonstop from Chicago to New York for $250 roundtrip on American.
Searching American, I found seats departing ORD on Thursday, August 29, returning from LGA on Tuesday, August 3.
This fare includes a carry-on bag plus one small personal item. A checked bag costs $30 each way.
This ticket includes seat selection which you can select when booking.
You'll find lower fares available in basic economy, though advanced seat selection is not included.
Check out other Labor Day finds here.
Need a room in New York? Here's what's available for the above dates on Hotelwatchdog.