Compared to O'Hare, Midway is a much smaller international airport, and it only carries a few airlines. Midway generally operates Southwest Airlines flights and it is much smaller and less busy than O'Hare. The advantage of traveling through Midway is that it is much closer to the city.

For a 2026 trip to Chicago, the "better" airport depends on your airline loyalty and destination. O'Hare (ORD) is the "International Giant"—better for travelers seeking a wide variety of airlines (hubs for United and American), hundreds of daily non-stop flights, and numerous high-end lounges. It is further from downtown (approx. 50–60 minutes) but connected by the 24/7 Blue Line train. Midway (MDW) is the "Convenience King"—better for domestic travelers, particularly those flying Southwest Airlines. Midway is much smaller, significantly closer to the Loop (approx. 25–35 minutes), and connected by the Orange Line. In 2026, Midway remains the preferred choice for locals and business travelers who want a faster "curb-to-gate" experience with shorter security lines. However, if you are flying internationally or want the amenities of a world-class hub (including the new Terminal 5 upgrades), O'Hare is the superior choice despite its massive size and the "long walk" between gates.