It's approximately 21-23 hours with a few short stops
That would depend on where you're travelling from. If you're driving from Tampa, FL it takes about 22 hours. If you're travelling from Milwaukee, WI it takes about 1.5 hours. If you're driving from Phoenix, AZ it takes about 36 hours.
2 and 1/2 hours
17 hours
MapQuest estimates the driving time as 18 hours and 40 minutes.
The shortest time is 39 hours.
3 and 1/2 hours
MapQuest estimates the driving time as 7 hours.
MapQuest estimates the driving time as 4 hours and 10 minutes.
The driving distance between Chicago, IL and Tampa, FL is approximately 1175 miles. The driving time would be approximately 19 hours 30 minutes if you were to travel non-stop in good driving conditions. (The driving time does not take into consideration conditions which may extend trip time such as weather, road work, border crossings and rush hour traffic in urban areas.)
Google Maps estimates the driving time as 19 hours and 15 minutes.
MapQuest gives the estimated driving time as 4 hours and 21 minutes.