Multiple airlines are offering cheap fare between Chicago and Tampa or Miami for as low as 67$ round trip non-stop. You can find more choices around 100$ which is still a steal for round trip flight.
Airline: Frontier / American
Sample Stay: 7 Days
Availability: Selected dates in November/December/January
See below chart for details (sample fare for Tampa, but Miami is about the same)
Book your trip on Priceline, Travelocity, Cheaptickets, Cheap-o-air
