From bad weather to busy terminals, booking a trip during the holidays can be a gamble.
Despite all the preparation, travelers face the unpredictability of flight delays and cancellations.
But which airports pose the greatest risk for travel disruptions during the bustling holiday season?
To find out, aGamble.com took an in-depth look at flight punctuality data across the United States, specifically focusing on departures during the holiday season. We analyzed flight record data provided by the Bureau of Transportation to determine which airports are the riskiest to depart from during the holidays.
Our study ranks the top 50 largest airports within major cities across the U.S. based on their track record of delayed and canceled flights during the holiday season. Additionally, we also determined which airports have the best punctuality and on-time flight arrivals.
Highlights:
- Among the 25 airports facing the most delayed or canceled flights during the holiday season, 4 are in Texas, 4 in Florida, and 4 in California.
- Chicago Midway International and Orlando International top the list, with more than 4 in 10 flights being canceled or delayed at each airport during the holidays.
- Seeking on-time departures? You’ll have better luck at Charlotte Douglas International, Washington Dulles International, or Detroit Metro Wayne County Airport, which are home to the most on-time departures during the holidays.
Which airports have the most delayed flights during the holidays?

Holiday headaches can be found in droves at Chicago Midway International, where an icy runway results in glacial departure times: 42.9% of flights from Thanksgiving through New Year’s were dropped or delayed last year.
When the weather in Chicago gets even colder after the Thanksgiving holiday, over half (54.3%) of flights during December and early January holiday period were canceled or delayed.
While Orlando International Airport is a gateway to the “happiest place on earth”, transportation magic is often in short supply. MCO occupies the No. 2 spot on our list, with difficulties arising primarily around the Thanksgiving holiday period.
Elsewhere, Fort Lauderdale-Hollywood International, with access to Miami’s sunny shores, follows close behind for holiday travel woes.
Of the 25 airports struggling to provide timely departures, 4 are based in Texas, 4 are based in Florida, and 4 are based in California, showing that the inclement weather the season brings isn’t always the biggest concern.