Obama crossed the line into areas that seasoned politicians never go, the politics of snow.
The differences between Chicago and D.C. are numerous, but those that would affect school delays and cancellations the most are the ability to remove snow from the roads and keep them properly sanded. North of NYC and you are golden. The snow plows and sanders are legions and the roads are usually plowed to pavement with adequate sanding in time for morning/evening commutes. D.C. does not have the heavy equipment or staffing that Chicago has. The vehicles in DC also do not have the standard all weather tires that the vehicles in Chicago are equipped with. The list could really go on, but he is a true jackass for even joking about the weather in this way.
Folks may not remember that you kept only a few of your promises, but they have memories like elephants when it comes to their street getting properly plowed, and whether school was called or not when it was treacherous to walk the length of your street to the bus stop. Any local politician will tell you -- play snow wrong and you can kiss your seat goodbye.
Silly rookie move Mr. President.