The insider's guide, from travelers who've actually been through.
Chicago Midway is the city’s smaller, closer-in airport on the Southwest Side, roughly 10 miles from the Loop and a good deal nearer downtown than O’Hare. It is a major base for Southwest Airlines, which dominates the flight board, so if you are flying Southwest domestically there is a strong chance you pass through here. Midway is compact and mostly operates from a single unified terminal with three concourses (A, B, and C), which keeps things simple and walking distances short.
Before your layover here
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The Orange Line is the local favorite for speed and value, especially if you are heading anywhere near the Loop.
Midway punches above its weight on food, leaning into Chicago staples, so you can grab deep-dish, local hot dogs, and decent coffee alongside the usual chains. Free wifi is available throughout. Lounge options exist but are limited compared with a big hub, so plan around the concourse dining if you have time to kill. The main food hall area near the concourse junction is the heart of the place.
As a largely domestic, single-terminal airport, connections are usually straightforward and you often will not need to re-clear security. Because downtown is so close and the Orange Line so quick, Midway is one of the better US airports for actually leaving during a longer layover, just watch your gate time and rush-hour crowds.
Use the tools above to check whether your layover is long enough to leave, and how the transit, immigration, and security timings add up for MDW.
