On December 8, 2005, a Boeing 737-7H4 operating as Southwest Airlines Flight 1248 crashed during a botched landing attempt at Midway International Airport. The plane overran the runway and struck two passenger vehicles on a road adjacent to the airport. A young boy was killed and others were injured.

Southwest Airlines has a remarkably strong safety record, but it has experienced a few notable accidents in its history. For many years, the airline was famous for having never suffered a passenger fatality due to a crash. However, this changed in April 2018 with Flight 1380, where a catastrophic engine failure led to debris breaking a cabin window. This resulted in a rapid decompression that tragically caused the death of one passenger. Other significant incidents include a 2005 event at Chicago Midway where a plane overran the runway in a snowstorm, striking a car on a nearby street and killing a young boy inside the vehicle. In 2000, a flight overran the runway in Burbank, California, though there were no fatalities in that instance. Despite these events, Southwest remains one of the safest airlines in the world, having operated millions of flights since 1971 with very few hull losses or fatal accidents compared to the industry average.