National Cheap Flight Day on PIX11: Darley Newman's Insider Tips for Cheap Fall & Holiday Flights
Insider Booking Tricks from Darley's PIX11 New York Living Segment
If you've been waiting for airfares to finally come back down to earth, this is your moment. This Sunday marks National Cheap Flight Day — the point in the calendar when summer travel slows down, school is back in session, and airlines start cutting fares to fill empty seats.
Emmy Award-winning host of Travels with Darley and author of Revolutionary Road Trip, Darley Newman sat down with PIX11's New York Living to explain what National Cheap Flight Day actually means for travelers, when to book versus when to fly for the best holiday deals, and three destinations — one Midwest classic, one Caribbean escape, and one French coastal gem — where the deals are already looking good for fall and the holidays.
Darley Newman on Pix 11 in New York City
What Is National Cheap Flight Day?
National Cheap Flight Day falls each year as summer travel winds down. As Darley explains it, this is "the time when we're transitioning from that busy summer travel season. Kids are going back to school. People are not booking as much. There's more inventory coming up. Airfares are going to start dropping."
It's less a single magic day and more a signal to start paying attention.
Is National Cheap Flight Day the Day to Actually Book Your Flight?
Not exactly — and that's the tip most people miss. "There's no one certain day where it's gonna be dropping," Darley says. "The airfares fluctuate every day and by the hour a lot of times, but this is the time when you're gonna start to see things dropping and you can look ahead, especially to holiday travel, and get started, get organized, set your alerts again so that you can be prepared when you do want to book."
Her go-to tools: Skyscanner and Google Flights, with fare alerts turned on well ahead of when you actually plan to travel.
Booking Date vs. Travel Date: Which Matters More for Holiday Flights?
When it comes to holiday travel, Darley says the date you fly matters more than the date you book. Her advice: fly on the days nobody wants to.
"Who wants to really travel on Thanksgiving, on Christmas Eve, Christmas Day?" she says. "But if you want to get a good deal on your airfare, those are the days to actually book. Airports are empty on Christmas Day."
Her rule of thumb for Thanksgiving week: skip the Sunday everyone's flying home. "Look for the Monday after. Look for the Monday before." The same logic applies around Christmas — and flexibility on your exact travel days goes a long way toward finding a lower fare.
3 Holiday-Deal Destinations Darley Recommends This Year
Chicago
"I love Chicago in general," Darley says, and the numbers back her up — with heavy flight inventory into the city, deals are easier to find. She's seeing November fares in the $200–$250 range, with United worth checking. Time it around the Magnificent Mile Lights Festival just before Thanksgiving for a full holiday atmosphere, hit family-friendly spots like Tilt 360, admire the architecture, and check out The Drake, her hidden-gem pick on the Mag Mile.
Puerto Rico
For a warm-weather holiday option, Darley points to Puerto Rico, with November and early December fares hovering around $225–$250 on carriers like JetBlue and Frontier. Her must-dos: El Yunque rainforest, the beaches, the colonial architecture of Old San Juan, and an arepa while you're at it.
Nice, France
For travelers chasing a European holiday market, Darley recommends Nice. Round-trip fares on Air France and American are landing in the low $700s for November into mid-December — and hotel rates drop along with the crowds. She's visited Nice's holiday market in person: think mulled wine, socca (a chickpea flatbread), and artisan crafts, plus the option to combine a coastal stay with a day of skiing just an hour away.
Darley's #1 Booking Hack
"Plan ahead and look now," Darley says. "I love Skyscanner and Google Flights recently — that's where I'm tracking my flights, and I travel a lot." Her closing advice for anyone hesitant about booking around the holidays: don't rule out traveling on the day itself. "I've done it many times, and it's wonderful. It's so easy."
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