
1) Thomas Restaurant - The rooftop area is great and the 39th street location allows me to eat in relative peace without gunshots or crappy buildings blocking my view (KU Med is across the street though). They have good food and good solid drinks.
2) Jaywalkers - The outside deck is actually pretty cool. The food is always pretty average but the beers on tap are relatively diverse featuring a ton of Free State offerings.
3) McCoy's - This deck is prime real estate in the middle of Westport. I won't go on about what you'll find at McCoy's because there are a million reviews of this place, but suffice it to say, this place is yummy. It's sister restaurant next door, The Foundry, also features a cool deck setting.
4) Pizza 51 - Part neighborhood Pizza joint, part kid's romper room, this UMKC area pizza place has three times as much seating space outside as it does inside. Good value and good pizza.
5) Sol Cantina - The great thing about 31st Street neighbors Sol and the Velvet Dog is their ample outdoor dining area. Probably more of a bar setting that a food setting but the space works for both.
6) Any Place with the sliding windows that open up. From All-Star Pizza to The Flying Saucer to Extra Virgin. I love the sliding window concept and it allows me to act as though I'm dining outside while still enjoying the vibe of the restaurant.
I know I just mentioned a few of the many great KC outdoor spots. Some places try to market the outdoor feel but they fail miserably. It your outdoor location is just a glorified smoking/cell phone area you don't count in my book (see Tower Tavern and the Westport Flea Market as examples). Likewise, you don't count if a few tables are thrown outside by a crowded street or sidewalk (see M&S Grill, Room 39, nearly every place in the Power and Light District, and La Bodega).