MDW · Restaurants

Harry Caray's Shortstop

A ★ 4 $$$$

Draft beer and Cubs memorabilia in Midway’s Concourse A

In Main Terminal Concourse A, Harry Caray’s Shortstop turns a standard airport bar into a mini shrine to Chicago baseball, with Cubs photos over the bar and TVs locked on sports. It sits along Concourse A by the gates, so you’re eating steps from your boarding area instead of trekking back toward the food court. Figure on a solid sports-bar menu and a 4.0-ish rating from Google to match.

Menu basics run to burgers, wings, and sandwiches, with most mains landing around $15–$20 and draft beers often in the $9–$12 range. Think burger-and-fries, buffalo wings, and basic sandwiches rather than anything that needs finesse. Portions skew “airport hearty,” so a single entree can easily cover a normal mealtime layover. This is not the cheapest option in MDW, but you’re paying for the sit-down setup and the bar TVs.

Regulars on Google and FlyerTalk say the move is to grab a bar stool instead of a table; bartenders tend to move quicker, especially during game days or peak afternoon banks. They’ll knock out a burger-and-beer order faster than the stretched-thin floor staff. Most frequent flyers stick to simple things: a cheeseburger, wings, or a basic sandwich plus a draft beer, and skip anything that sounds like a “chef special.”

Watch out for slow ticket times when the concourse is full and multiple flights out of A are delayed at once; reviews mention 20–30 minute waits for food and the occasional lukewarm plate or overcooked burger. Tabs also climb fast if you stack cocktails on top of a $18 entree. If your connection at MDW is under an hour, treat this as a drinks-and-fries stop, not a full sit-down meal.

Tip: Check your gate on the Midway screens before sitting; if you’re departing from the far end of Concourse B instead of A, build in a 10-minute walk and ask for the check as soon as your food arrives.

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