You can find flights at this price starting in late November through March 20, 2019. Departure days are available daily, however, dates are starting to sell out quickly so you'll need a flexible travel window to help find dates that work for you.
Searching on AA.com, I found seats departing ORD on Saturday, January 19 and returning from TPA on Tuesday, January 22, 2019.
We are seeing loads of great deals departing Chi-town today, so click your way over to our O'Hare (ORD) and Midway (MDW) flight deal pages to see what other discounted destinations we have marked down for you.
Looking for a room in Tampa? We've got a large list of hot hotels available for the mentioned dates on Hotelwatchdog.