The driving distance between Billings, MT and Milwaukee, WI is approximately 1175 miles. The driving time would be approximately 18 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.)
23 hours
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.
8 hours and 24 minutes
Check Mapquest.com
20 hours
a long time
It will require about 28.5 hours to drive that 1,781 miles.
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.
From Billings and Seattle it is 819 mi (about 11 hours 37 mins).
According to mapquest it takes 22hrs and 34mins to drive from Milwaukee Wisconsin to Naple's Florida.
It takes about 9 and a half hours.