The landing has radiant heat in slab and is also pitched toward a 6" floor drain at the farthest point away from door. This drain is tied to the perimeter footing/foundation drain tile. This was built in Illinois and we have lots of rain and snow such as blizzard of 2011 which occurred after completed and no issues! Absolutely it could be covered with a roof. By the way, the code compliance officer did require us to install safety railings which the homeowner removed after inspection.

Is there a sump pump in this home .. I know chicago has that flood issues, how do you keep water from backing up into the basement?

With the heavy clay soils in Illinois, plus the amount of precipitation we get here, you always need to consider drainage when you have that much hardscape covering the surface of the land. Other techniques include rain barrels or rainwater harvesting systems, permeable and pervious pavers as a means of reducing the amount of water that is funneled into storm water drains during a rain event. Leaf drop is something you have to deal with in the fall, but from that photo there doesn't seem to be a tree in the immediate area.