Flying is not faster 90% of the time for what you describe. And it’s way less reliable and more stressful. Getting in your own (positive space) car with your own music, phone calls, etc. is the way to do it. No waiting for delays or whatever.

I had a 3-hour, 186 mile drive until I moved to Chicagoland. I drove it most of the time even though flying was occasionally a good option.

Flying to ORD and then getting to MDW would, for me, never ever be ahead of driving.