I like to drive, but I'm not so enthusiastic about driving more than about five hours. Other factors that matter for me would be expected traffic or road construction issues, whether I need a car at the destination, whether it's a pleasant/scenic drive, and whether the destination is a downtown area of a big city (and thus has bad traffic as well as expensive valet parking). I'm more likely to drive if I'm familiar with the area and less likely to drive in winter. Often I choose to drive because I like the convenience of coming and going when it's good for me.

Also, my five hour radius involves generally small airports, with MSN being somewhat of an exception, and often regional jets: Duluth, Green Bay, Rochester, Sioux Falls, and smaller places. The far northern suburbs of Chicago are about seven hours, with Milwaukee being a bit less. Sometimes I'll do a drive in two days if there's a good place to stay along the way and I have the time. Last summer I drove 1300 miles in three days to avoid a very early morning mainline hub-hub flight followed by a connection to a twice-a-day regional jet.

Some employers have mileage limits on how long of a trip they'll reimburse if one drives either a personal or rental car. Others have fleets of loaner cars that can be used to drive for a business trip. Yet others will compare the cost of driving versus flying to determine whether driving is permitted for business travel.