For travel over the Labor Day holiday, fly nonstop from Boston to Chicago for $299 roundtrip on American.
Searching AA.com, I found seats departing BOS on Friday, August 30, returning from ORD on Tuesday, September 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.
Lower fares are available in basic economy, though advanced seat selection would not be included.
Check out other Labor Day finds here.
Need a room in Chicago? Here's what's available for the above dates on Hotelwatchdog.