He had been a horrible man his entire life and has been sent to HELL.
The devil puts him to work breaking up rocks with a sledgehammer. To make it worse he cranks up the temperature and the humidity.
After a couple of days, the devil checks in on his victim to see if he is suffering adequately. The devil is aghast as the Chicagoan is happily swinging his hammer and whistling a happy tune.
The devil walks up to him and says, "I don't understand this. I've turned the heat way up, it's humid, you're crushing rocks; why are you so happy?"
The Chicagoan, with a big smile, looks at the devil and replies, "This is great! It reminds me of August in Chicago. Hot, humid, a good place to work. It reminds me of home. This is fantastic!"
The devil, extremely perplexed, walks away to ponder the Chicagoan's remarks. Then he decides to drop the temperature, send down a driving rain and torrential wind.
Soon, Hell is a wet, muddy mess. Walking in mud up to his knees with dust blowing into his eyes, the Chicagoan is happily slogging through the mud pushing a wheelbarrow full of crushed rocks.
Again, the devil asks how he can be happy in such conditions. The Chicagoan replies, "This is great! Just like April in Chicago. It reminds me of working out in the yard with spring planting!"
The devil is now completely baffled but more determined to make the Chicagoan suffer. He makes the temperature plummet. Suddenly Hell is blanketed in snow and ice.
Confident that this will surely make the Chicagoan unhappy, the devil checks in on the Chicagoan. He is again aghast at what he sees.
The Chicagoan is dancing, singing, and twirling his sledgehammer as he cavorts in glee.
"How can you be so happy? Don't you know its 40 below zero!?" screams the devil.
Jumping up and down the Chicagoan throws a snowball at the devil and yells, "Hell's frozen over!! This means the Cubs won the World Series!!"