Burnt end sandwiches from either Jack Stack or Smokehouse, at least twice per month.
A few times a year I crave a good chocolate peanut butter malt so I go to Sheridans or Ben & Jerrys.
A good steak, at least once a month, I either grill it myself with garlic mashed potatoes & asparagus and eat at home or go to a good steakhouse. Last steak I had was actually at Houstons on the Plaza, they have a Hawaiian Ribeye that is amazing, they marinate the steak for 3+ days in pineapple and soy sauce, sounds weird but just trust me.
Last craving is the drink called a caipirinha that I have to have at least once a year, preferably in the summer, only place in KC I've found that serves them is McCormick & Schmidts.
http://en.wikipedia.org/wiki/Caipirinha