
by Mia Taylor
Last updated: 2:10 PM ET, Fri May 9, 2025
Memorial Day weekend and the start of the busy summer travel season is upon us. And along with the annual excitement surrounding the hazy days of summer, there’s also a little turmoil.
Flight delays and disruptions have reached an all-time high due to major disturbances in the aviation industry, including widespread technology failures, airline staffing shortages, and air traffic control issues. (The recent chaos at Newark Liberty International Airport is just the most recent example of all this.)
The roll-out of new REAL ID requirements this past week has only worsened the situation, triggering confusion and even longer airport lines.
Meanwhile, TSA advises passengers to arrive at the airport at least three hours before their flights for Memorial Day weekend.
Given all the drama, traveler are understandably, more than a little concerned.
New data from travel insurance comparison site Squaremouth shows that 48 percent of Memorial Day travelers say their flight being delayed or canceled is their number one travel concern this year.
That's a significant spike from last summer, when just 36 percent of travelers cited a flight delay or cancellation as their biggest Memorial Day weekend concern.
At the same time, searches for delay-related travel insurance coverage for Memorial Day weekend have surged 55 percent year-over-year, according to Squarmouth.
Translation: Travelers are preparing for the worst.
“Recent disruptions and delays, along with ongoing economic uncertainty, have led some Americans to adjust their travel plans— (including) favoring closer or more affordable destinations,” Squaremouth’s Ned Tadic told TravelPulse. “Nonetheless, they remain eager to travel this summer.”
If you’re forging ahead with Memorial Day weekend flight plans, read on for a few helpful tips.
Making the most of trip delay insurance
If the drama surrounding air travel has you a little rattled, here’s what to know about securing the best possible travel delay insurance coverage:
- Travel delay insurance can cover such costs as meals, hotel stays and transportation
- Most travel insurance plans include standard travel delay coverage but read the fine print because not all coverage is equal. Key differences can have a significant impact on how helpful a policy will be.
- To get the most flexibility out of your travel delay insurance, look for a policy that kicks in after flight delays of three hours, suggests Squaremouth. "The best travel insurance plans for trip delays offer short wait times
for coverage to begin," says a Squaremouth blog on the topic.
- It’s also a good idea to ensure your coverage accounts for any delay caused by a common carrier.
- Make sure the policy also covers missed connections after three hours
- Look for plans that offer generous reimbursement limits.
Some of Squaremouth’s top picks for best flight delay insurance plans
include Travel Insured International’s Worldwide Trip Protector; John
Hancock “Gold”; Trawick’s Safe Travels Voyager plan; IMG’s
iTravelInsured Travel LX Basic policy; Seven Corners Trip Protection
Choice and Nationwide’s “Prime” policy.

(Photo Credit: Courtesy AdobeStock)
Best and worst day to fly
Squaremouth isn’t the only company hoping to help travelers prepare for the busy holiday weekend ahead.
NerdWallet recently released a report on the best and worst time to travel for the holiday, indicating that for the past three years, the Friday before Memorial Day was the most crowded day to fly, with an average of 2.69 million passengers boarding planes that day.
As for return travel, it seems that the Sunday following the holiday is the one to avoid. Meaning it is the busiest day at airports with an average of 2.62 million passengers taking to the skies.
So, what are the best days to fly, you ask? The answer is less than ideal for those hoping to maximize their holiday weekend getaway, but the least crowded day to fly before Memorial Day was the Saturday before the holiday, with a three-year average of 2.21 million people flying that day.
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