Distance

Orlando to Madison (Wisconsin) is 1300+ to 1400+ miles depending on the route you choose.
Example1. If you travel on the I-75, I-24, I-57 and I-39 via Atlanta, Nashville and Bloomington (Illinois) (1300+ miles) the half-way point is Murfreesboro at roughly 655 miles or Nashville at roughly 685 miles.
Example 2. If you travel on the I-95, I-77, I-64, 35, I-65 and I-90 via Jacksonville, Savannah, Charlotte, Dayton, Indianapolis and Chicago (1400+ miles) the half-way point is Beckley WV at roughly 730 miles or Charleston (West Virginia) WV at roughly 780 miles.