Consider entering at Gardiner, Montana which is 1,344 miles and an estimated driving time of 21 hours and 28 minutes from Milwaukee.
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.
24 hours
Depends on the route you take and what gate you go into. I drove to Yellowstone from California in 4 days. There is a good KOA in Jackson.
Check Mapquest.com
20 hours
I assume you mean Milwaukee, Wisconsin (as opposed to Milwaukee, North Carolina). The distance to New Orleans from Milwaukee is 912 miles. How long that distance would take you to drive depends on how fast your average speed is. Driving an average of 50 MPH, it would take you 18.24 hours.
a long time
It will require about 28.5 hours to drive that 1,781 miles.
According to mapquest it takes 22hrs and 34mins to drive from Milwaukee Wisconsin to Naple's Florida.
Approximately 10 hours
It takes about 9 and a half hours.