Chicago pizza box to check? Connie’s in Central Market.
Connie’s Pizza sits in the Main Terminal Central Market, airside, so you can grab a slice without leaving security. It runs as a quick-service counter with pies in the case and a few seats nearby, and most reviewers land around a 4-star rating. Think hometown Chicago brand, not tourist-trap chain, and very much “good enough before boarding Southwest out of MDW.”
Hours aren’t clearly posted online, but regulars report it open across most flight banks from early lunch through late evening, matching other Central Market spots. Prices hit the airport norm: slices around $7–$9, with combo meals (slice, side, drink) drifting into the mid-teens. That puts Connie’s in the $$ tier, more than McDonald’s down the concourse but less than a sit-down bar tab.
Order the sausage or pepperoni slice first; multiple reviews call those the most reliable options, with decent pan-style crust rather than true deep dish. Deep-dish pans show up less often and can take extra time if they’re baking a new one, so don’t bank on that if your boarding time is under 30 minutes. Cheese-only pizza is there, but complaints about bland flavor pop up more for the plain pies.
What regulars do: eyeball the case and ask for a reheated or fresh slice if the pizza under the heat lamp looks tired. People on FlyerTalk mention grabbing a sausage slice and a draft beer, then eating at the shared Central Market seating instead of waiting on table service. That move keeps you in sight of multiple gate screens in the main hall.
Watch out for lukewarm slices and soggy crust if the staff is slow to rotate pies, plus a thin topping lineup during off-peak hours. Practical tip: if your flight is delayed by 20–40 minutes, this is a solid spot to grab one reheated slice and a beer, then carry it to a seat with a nearby outlet.