Is it easier to get to downtown Chicago from MDW or ORD?

It's really just as easy from either one. O'Hare has the blue line and Midway has the orange line they will both take you downtown. The orange line coming from Midway only has 8 or 9 stops, the blue line coming from O'Hare to downtown has about 15 stops along the way. Midway would be the easier to navigate, O'Hare is just huge and Midway is also less busy.