Pizza delivery to Midway airport in Chicago
 

I have a 1 1/2 hour long layover in midway and would like to preorder a deep dish and have it delivered to the airport. Is that a thing? How do I go about picking it up and going back through the security gate?

Almost impossible to coordinate. There's a Lou Malnati's and a Giordano's in the general vicinity, but delivery orders take 45-60 minutes to fulfill. You'd have to exit security, find a way to meet a delivery guy on the curb, then try -- try -- to bring the pizza back in through TSA. And with current TSA sickouts the single MDW security checkpoint can have up to a 30-minute wait. Just visit Home Run Inn on the concourse.

Suspect whoever you call will think it is a prank. If they don't, not sure how this works logistically so that you make it back to board your connection and still enjoy the pizza.

Assuming that your inbound in on time and there's no problem bringing the pizza through security, the plan is theoretically doable. I once had my sister deliver a cake to the MDW departures curb (long story). She called as she pulled up and I went out and met her. TSA didn't bat an eye bringing the cake back through security. Obviously that was a little different since it wasn't a commercial delivery.

It may also be easier to just order the pizza for takeout (specifying a sufficiently early time) and hop in a cab to retrieve it. It would likely be more expensive than delivery, but the locations BearX220 mentioned are both very close to the airport.

In either case, having Pre-Check would make it a lot more comfortable.

This is absolutely possible. I have done it multiple times with Lou Malnati's. Depending on the length of your layover, you can call and order once your flight lands or call before your flight takes off and let them know when you would like to have it delivered. They have always been very accommodating and happy to deliver. They will ask you where you would like to meet them - Departures or Arrivals and which door number. You can find maps online so just choose one near the terminal for the airline that you're flying. Midway isn't huge so just pick a door in the middle of your terminal and you should be golden. I always give them a nice tip for making it such an easy purchase - and much cheaper and delicious than airport food! I have TSA so getting it back through security is super easy. I typically leave my carry on with my spouse so it's just me and my pizza to get back through the checkpoint but there's no restrictions on bringing pizza through security.

BirdieD - Welcome to FlyerTalk. Great, informative first post!

This might be the most useful first post in Flyertalk history.