Chicago Midway Airport is a one mile square piece of land in the middle of a neighborhood. What’s the Biggest Plane to land at Chicago Midway Airport?
Nestled in a neighborhood on the south west side of Chicago is Chicago Midway International Airport. This airport has been affectionately referred to as a ‘postage stamp’ due to its tiny footprint relative to most other airports in the United States.

The airport features four runways at each corner of its one mile square. The longest runway tops out at less than 6,500 feet. While it is long enough for daily operations of single aisle airliners like the Boeing 737 and Airbus A320, it’s not really large enough to handle much bigger.
Midway occasionally sees Boeing 757s

Back in the late 1990s and early 2000s, the Boeing 757 was a daily visitor to Chicago Midway Airport. American Trans Air or ATA regularly flew both the Boeing 757-200 and even larger 757-300 into the field.
The jet stuck out like a sore thumb because of its size but its well-known short field performance meant that it was a relatively benign operator into the field.
While 757s are less common today, both United and Delta still occasionally fly their 757s into Midway on charter flights as you can see in the video below.
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Even Bigger: An Airbus A300 Flew Into Midway Once

Back on 3 October 1973, Midway saw its largest airliner. The A300 prototype landed at Midway as part of a promotional tour in the United States.
Fully loaded, an Airbus A300B is a 300,000 lb aircraft. The airliner typically seated 210 to 250 in a three class, dual aisle arrangement. Many people (including avgeeks) incorrectly assume the the A300B was the largest plane ever to land at Chicago’s Midway Airport.
So What’s the Biggest Plane At Chicago Midway?
The answer might surprise you. It’s actually not an airliner at all. And you can still occasionally see this plane land at Chicago’s south side airport.
The answer is: The C-17 Globemaster III. This Air Force airlifter is massive with a length of 174 feet and a wingspan of 169 feet. Fully loaded, the jet tops out at 580,000 lbs.
While a fully loaded C-17 would comfortably require more distance for takeoff at Midway, the jet can still pick up cargo and comfortably land and takeoff from the airport. The C-17 has the ability to land on relatively short runways, as little as 3,500 feet.
The C-17 typically lands at Midway to support VIP movements. You might see the jets there this month as the President and Vice President prepare for the Democratic Convention that will be held in Chicago.
