Chicago Midway (MDW): The Complete Layover Guide

Midway is the simplest big city airport in America. Check in, security and baggage claim live in the main terminal east of Cicero Avenue; the gates live in a separate concourse building on the other side of the street.

The two halves connect with an enclosed pedestrian bridge that carries you over six lanes of Cicero traffic. You clear security in the main terminal, walk the bridge, and come out in the Central Market, the food and retail hub where all three concourses meet. From there, Concourse A is to your left, Concourse B straight ahead, and Concourse C to your right. Everything is airside, everything connects, and nobody screens you twice. A bad gate to gate walk here is measured in minutes, not in trains and buses.

This is Southwest's Chicago fortress. The airline operates the overwhelming majority of departures, and the whole building breathes with its schedule: quiet between banks, then a surge of rolling bags every couple of hours. Southwest sells plenty of connections here under an hour, and the geography supports them when the inbound runs on time. The flip side is the morning crush at security, when half of Chicago seems to be flying somewhere warm. The checkpoint feeds every gate, so budget extra time at dawn, on Mondays, and around holidays.

The food took a real step up with the airport's $400 million modernization, which grew the concessions space from 40,000 square feet to more than 70,000. The Central Market at the junction of Concourses A and B carries the new flagship names, including Connie's Pizza and Beecher's Handmade Cheese, and older maps still label this stretch Midway Boulevard. Deeper into Concourse A, a second Food Hall lines up Chicago staples such as Billy Goat Tavern and Arami, and Garrett Popcorn does its usual brisk trade. For an airport this size, eating well is not a problem.

Wifi is free throughout the terminal on the airport's official network. It is ad supported, so expect to tap through a short ad before you connect, and it held up fine for mail and streaming on our checks of traveler reports. Power outlets are scattered rather than everywhere, so claim one when you see it.

Timing honesty: arriving 2 hours before a domestic departure is comfortable at Midway, and often generous outside the morning banks. Connecting on a single Southwest ticket, 45 minutes is workable. Self connecting on separate tickets with checked bags, treat it like any other airport and give yourself 2 to 3 hours, because the bag carousel and the checkpoint queue do not care how compact the building is.

Midway has one of the best airport to downtown transit links in the country. The CTA Orange Line station is attached to the terminal by an enclosed walkway, and the ride to the Loop takes about 25 minutes for a standard CTA fare, with no airport surcharge at Midway. That surcharge is an O'Hare thing. Trains run from roughly 3:30 am to about 1:25 am on weekdays, with slightly later starts on weekends, and CTA has announced plans to extend the Orange Line to 24 hour service with new transit funding; the start date is to be confirmed. It is the L, so expect station stops all the way in rather than an express run.

That makes a city escape realistic on a longer layover. With 5 hours or more between flights, you can be looking at the lake or eating a proper deep dish downtown with time to spare, as long as you protect a 2 hour buffer for the return trip and security. With less than 5 hours, stay put and let the Food Hall do the work.

Overnight is where Midway gets honest with you. The building technically stays open around the clock, but from midnight to 4 am access is restricted to ticketed passengers, and the security checkpoint closes overnight, which pushes everyone landside. The lights stay bright, the announcements keep rolling, and the building runs cold. During mass cancellations the airport has brought out cots for stranded passengers, but on a normal night you are working with benches. The better play is the Midway Hotel Center, a cluster of chain hotels just south of the terminal on Cicero Avenue; the Hilton Garden Inn there runs a free 24 hour shuttle about every 20 minutes, and its neighbors operate similar service.