The driving distance between Miami, FL and Milwaukee, WI is approximately 1465 miles. The driving time would be approximately 24 hours 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.)
MIAMI
Google Maps estimates the driving time as 25 hours.
st louis to milwaukee
It would take much longer to drive the 1214 miles to Miami, FL than to Milwakuee WI (374 miles).* If you are driving to Miami, Ohio (366 miles), it is slightly less time than to Milwaukee.
Milwaukee is MUCH closer to St. Louis than Miami is; you could drive from St. Louis to Milwaukee, back to St. Louis again, and almost to Milwaukee a second time in about the same amount of time it would take to drive from St. Louis to Miami once. In fact, the just the part of the trip that's actually in the state of Florida is greater than the entire distance from St. Louis to Milwaukee.
It is not possible to drive from Miami to Cuba.
That is a fairly short drive depending on where in Milwaukee you live. Worst case is about an hour.
If you were to drive from Austin to Milwaukee it would take about 19 hours and 2 minutes. That is assuming that you are drving to Milwaukee.
The drive from Charlottesville, VA, to Miami, FL, should take between 16-17 hours.
Check Mapquest.com
4 hours
about 2 days