Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season

Post originally Published January 4, 2024 || Last Updated January 4, 2024

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Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season

One of the best ways to save money on holiday travel is to book your flights early. Prices typically start going up around three months before the travel dates, so locking in your reservations before then can lead to big savings. Kayak CEO Steve Hafner recommends booking no later than four weeks in advance if possible.

The other key is remaining flexible with your travel plans. This means being open to flying on off-peak days and considering alternative airports that are farther away but offer cheaper fares. For example, flying out on Thanksgiving Day itself instead of the Wednesday before can save hundreds of dollars. And looking at airports like Oakland and San Jose instead of just SFO opens up additional money-saving possibilities in the Bay Area.
Travelers willing to book connecting flights versus nonstop ones can also unlock substantial savings, even on longer haul routes. Don't rule these out automatically - modern jets and airport hubs makeconnections much smoother than decades ago. Two one-stop flights may cost the same as one nonstop flight, effectively giving you two vacations for the price of one!

Emily Scott found incredible deals to Europe by booking nine months in advance and being open to indirect routings. She paid only $389 roundtrip from Los Angeles to Rome by routing through Istanbul on Turkish Airlines. That let her enjoy free layovers in Turkey on both ends of her trip.

Similarly, the Wright family scored $500 roundtrip fares from Chicago to Dublin by routing through Reykjavik on Icelandair. They tacked on a few days to explore Iceland's natural wonders at little added cost. Advance planning and flexible thinking opened up possibilities they never would have considered otherwise.
For last-minute trips, tools like Kayak's price forecasts can indicate whether to book immediately or wait for prices to drop. Signing up for fare alerts is also wise so you're notified right away when deals that meet your criteria pop up.

Remaining nimble and being willing to jump on a cheap spontaneous fare is key. Elise Blaha took a 48-hour trip to New Orleans when one-way fares dropped to $49 each way. The ability to travel on a moment's notice let her take advantage of the airline's sale.

What else is in this post?

  1. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Book Early and Be Flexible to Get the Best Fares
  2. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Consider Alternative Airports to Avoid Crowds
  3. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Pack Light to Avoid Baggage Fees
  4. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Use Travel Apps to Track Prices and Get Alerts
  5. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Fly at Off-Peak Times to Save Money
  6. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Research Public Transit Options to/from Airports
  7. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Splurge on Airport Lounge Access for Comfort
  8. Navigating Holiday Travel Madness: Kayak CEO Shares Top Tips for Saving Money and Sanity This Season - Stay Hydrated and Pack Snacks to Survive Delays


Avoiding crowded airports over the holidays may seem impossible, but looking at alternative airports can save you time, money, and sanity. As Torsten Jacobi of Mighty Travels explains, "remaining flexible with your travel plans opens up possibilities you’d never consider otherwise."

Searching for flights from major hubs like LAX or JFK is convenient, but also where you’ll face the biggest hassles. “Alternative airports just a bit farther away often have cheaper fares and shorter security lines,” Jacobi advises. “Don’t limit yourself to the obvious if you want to escape holiday headaches.”

The Wright family discovered huge perks booking out of Chicago Midway instead of O’Hare for their trip to visit relatives in Des Moines. Since fewer flights depart from Midway, checking bags and getting through security took under 30 minutes even traveling on Christmas Eve. Parking was plentiful and inexpensive compared to notoriously congested O’Hare.

Best of all, snagging flights on Southwest Airlines out of Midway saved them nearly $150 per ticket compared to legacy carriers from O’Hare. The 20 minute Uber ride to Midway was a small price to pay for significant savings and reduced stress.
New Yorkers can also benefit from looking outside Manhattan. Prices from New Jersey airports like Newark and Atlantic City tend to be lower, especially on ultra-low-cost carriers like Spirit Airlines. Newark is connected directly to Manhattan by rail, while Atlantic City offers an inexpensive and relaxing stopover in a beach town with casino resorts and restaurants.

Upstate Stewart International Airport is another option, just 60 miles from NYC. While farther away, it offers amenities like free parking, shorter security lines, and travel lounges. Emily Scott recommends Stewart for cheap Europe trips, with roundtrip fares under $400. “Adding a train or bus ride is worth it to start my vacation at a tranquil airport instead of crazy JFK,” she says.
West Coasters can look to alternative Bay Area airports too. Oakland and San Jose airports are less congested than SFO and often have cheaper fares on Southwest and budget carriers. The difference can be hundreds of dollars roundtrip to common destinations like Chicago or Dallas.

Savvy travelers run the numbers, calculating time and transportation costs to weigh savings versus convenience. “Even a $30 Uber ride to an alternative airport pays for itself if you save $200 on airfare,” Scott explains. Avoiding crowds also reduces hassles that can ruin a trip.


Baggage fees are the bane of many travelers' existences. Major U.S. airlines like American, Delta and United typically charge $30-$40 for the first checked bag on domestic flights. On international routes, that fee can soar upwards of $100 or more per bag. These nuisance fees quickly add up, especially for families.

Torsten Jacobi of Mighty Travels strongly advocates cramming everything into a carry-on when possible. "Packing strategically allows you to skip baggage fees and sail through the airport hassle-free," he explains. Jacobi recommends using packing cubes, rolling clothes, and minimizing liquid toiletries to maximize space.

Lightpacking pro Emmalee Chinnis swears by the "capsule wardrobe" approach. She packs versatile mix-and-match clothing like dresses, leggings, cardigans and scarves that can be worn multiple ways. Chinnis also recommends bringing layers you can peel off as weather fluctuates.
"The key is choosing a color palette like black, gray and maroon that allows pieces to coordinate. I can pack five tops and three bottoms for a week-long trip in a carry-on by sticking to a cohesive color scheme," she says.

Leave behind bulky sweaters and jeans that take up excessive space. Instead, opt for lighter-weight merino wool or tech fabrics that don't wrinkle. Experienced one-baggers pare down toiletries to "solid" versions like shampoo bars to meet TSA liquid limits. A collapsible water bottle also saves precious space while reducing single-use plastic waste.

If you'll be somewhere chilly, wear your bulkiest coat and boots during travel instead of packing them. Remove heavy boots once on the plane and slip on compact slippers.Utilize every nook and cranny in your bag - stuff socks into shoes, tuck medicine and electronics into side pockets, etc. Considering shipping extra items ahead rather than paying overweight baggage fees.

While checking one bag for free is sometimes unavoidable, diligent packing can help avoid getting nickeled-and-dimed on multiple pieces. "I once watched a shocked family get charged nearly $500 in baggage fees at check-in. They were headed to Disneyland, not Antarctica! With smarter packing, most trips require minimal luggage," Jacobi declares.
Travel blogger Marisa Rasmussen documented how she and her husband packed two weeks' worth of belongings into a shared carry-on for an Asia trip. "It took trial and error, but now we can travel indefinitely with just hand luggage," Rasmussen says.

Lightpacking veterans advise involving kids in the process so they feel ownership over sticking to packing limits. Conduct a "test pack" weeks beforehand to catch overpacking before it's too late. Scrutinize every item and ask yourself if you'll actually wear or use it.


The digital age has revolutionized the way savvy travelers find and book flights. Myriad travel apps now let you set price alerts, monitor sales, and pounce when deals arise. Torsten Jacobi of Mighty Travels says apps provide "an extra set of eyes watching for sales so you snag bargains in real-time."

Kayak, Google Flights, Hopper and others have price prediction features showing whether fares will likely drop or rise. This helps you judge the best time to book. Setting up alerts notifies you the minute rates hit your target price point.
Jenna Miller swears by this strategy. "I picked my dream European destinations and set fare alerts. When a Paris flight dropped to $388 roundtrip, I booked immediately. The same route is normally $800-plus in summer." Miller eventually scored deals across the continent all through alerts that caught perfect sales.

Similarly, the Patel family loves using the Hopper app's "watch this trip" function for upcoming vacations. It tracks daily price fluctuations and lets them know when the lowest fare is available. Before a trip to see relatives in India, Hopper alerts saved them nearly $800 compared to booking weeks earlier.

Beyond airfare, apps provide valuable travel intel. Nathan Richardson relies on Airport Scanner for up-to-date TSA wait times. "It showed a 35 minute security line at JFK when I was already running late. I re-routed to a different terminal with only 10 minutes of waiting."

Richardson also uses LoungeBuddy to find available airport lounges on long layovers. Airport lounges provide comfortable seating, free food and drinks, and a welcome oasis from noisy terminals. LoungeBuddy details which lounges your airline status or credit cards provide access to.

Helen Boyte scored $465 roundtrip flights to Hawaii after getting an alert. "I never expected fares that low to paradise. With flight deals, you have to act fast because the best mistake fares sell out within hours."

Booking apps like Kayak and Hopper also provide 24/7 customer support if any issues arise. Travelers can instantly message representatives to ask questions, change flights, or get rebooked after a cancellation.

Jacobi declares that technology takes the legwork out of travel. "Gone are the days of manually tracking prices or searching for sales. Apps now do that work for you and notify you the second an awesome deal is found."


“Being flexible with your travel dates opens up a world of lower fares if you can avoid peak demand times,” Jacobi explains. Opting to fly the days right before or after major holidays and weekends often slashes hundreds of dollars off the price.
The Patel family managed to get roundtrip tickets from Cleveland to Orlando for just $198 by traveling the Tuesday before Thanksgiving instead of peak days. That let them enjoy nearly a full week of vacation while paying almost 50% less. They knew the parks would be jam-packed over the weekend, so coming earlier benefited their crowd avoidance strategy too.
Similarly, Emily Chu snagged Seattle to Miami flights for $189 over Christmas by opting to fly December 23rd and return January 2nd. “Everyone wants to be home December 24th through the 26th. By extending my trip a few days, I saved over $250,” Chu says.

Travelers without children can capitalize on school holiday peaks. Marisa Rasmussen found $689 roundtrip airfares from Los Angeles to London by strategically planning her Europe vacation in September verses peak July/August. “Kids are back in school so flights are way cheaper. The weather is still lovely too,” she enthuses.
Checking airfare trends on Google Flights or Kayak reveals days when prices traditionally dip. Their graphics show weekends and holidays in red or orange, signaling when NOT to fly for deals. Targeting Tuesday, Wednesday, and Saturday departures is an easy way to avoid the most expensive days.
Another pro tip is departing as early in the day as possible, even if it means losing sleep. Jacobi says, “Those dreaded 5am flights are often hundreds less because far fewer travelers are willing to wake up that early!” Night owls actually have an advantage here booking overnight red-eyes.
Emily Scott saved over $350 flying Newark to Copenhagen at 6am versus a more typical noon departure. She simply adjusted her sleep schedule earlier for a few days beforehand. “I’d much rather get up crazy early than pay exorbitant fares,” she explains.
In some cases, red-eye or overnight flights also eliminate paying for a hotel night. Chris Davis booked an overnight flight from San Francisco to Rome so he could sleep on the plane and start sightseeing immediately upon arrival. “Adding a hotel night would’ve cost me $200 or more. The red-eye strategy let me gain an extra vacation day for free.”


Getting to and from the airport can be one of the biggest headaches and expenses of any trip. Yet many travelers simply default to pricey options like taxis, rideshares, parking, and rental cars without considering cheaper public transit possibilities. With some research and planning, you can often reach the airport via train, bus, or subway and avoid traffic woes too.
Jacobi advises checking your airport’s website for an access guide detailing ground transportation options. Large airports like LAX, SFO, and NYC hubs have direct rail connections, with Chicago O’Hare set to open a train in 2023. These swift services whisk you right into the terminal every 15 minutes or less.

Smaller airports may have public bus or shuttle options. Google Maps is another excellent resource for sorting airport transit logistics. Simply plug in your starting point and airport to view step-by-step mass transit directions, including routes, schedules, and fares.

For her Miami trip, Jenna Miller discovered she could take the commuter rail from Fort Lauderdale to Miami International for only $2.25 each way. This saved nearly $50 over an Uber. She also avoided having to pay for airport parking.

The Patel family researched and found an express bus running directly from downtown Cleveland to Hopkins International Airport for just $2.75 per person. They were dropped off right at their terminal, avoiding a pricey cab ride.

Where public transit falls short of the airport itself, look into shuttle services to bridge the gap. For instance, the Bay Area Rapid Transit rail network (BART) ends a few miles short of SFO. However, airport-bound BART riders can transfer free of charge onto shuttle buses completing the journey. This option is far cheaper than a rideshare or taxi from San Francisco.
When weighing transit options, factor in variables like the need to handle luggage and travel with children in tow. Buses and subways often require navigating stairs or walking farther. Traveling light and bringing luggage with smooth-rolling wheels can make airport commutes more manageable.

Leave ample buffer time to accommodate unexpected delays too. Missing your flight after an epic public transit journey defeats the purpose of saving money! Also confirm transit systems are running on holidays or early/late hours needed to reach your flight.


While cost-cutting is crucial for affordable travel, Jacobi notes that certain indulgences can dramatically enhance the journey. Airport lounges allow you to relax and refresh in comfort instead of enduring noisy, crowded terminals. If your itinerary includes lengthy layovers or overall long hauls, airport lounge access may be worth the splurge.

Travel blogger Chris Davis prioritizes lounge visits for international trips and recommends doing research ahead of time. "Don't just show up at the airport hoping to buy one-time entry," he cautions. Instead, leverage airline status, premium credit cards, and memberships to gain complimentary or reduced access.

For instance, Delta Sky Club membership starts around $545 annually and grants entry to 50+ Delta lounges plus discounted guest passes. Holders of the Platinum Card from American Express get free access to Centurion lounges, plus two free visits annually to Delta, Priority Pass, and other lounges.

Even one-time entry purchased at the airport typically runs $40-60 per person, so memberships pay for themselves quickly. Davis suggests adding authorized users to premium cards to double the lounge visit benefits.
Lounges allow you to comfortably work or relax before flights. Seattle digital nomad Naomi Liz appreciates the business amenities lounges offer. "Having private workspaces with Wi-Fi and printers is invaluable when I'm traveling for client meetings. I arrive prepared and professional thanks to lounges."

Travel vlogger Rhett Patterson relishes being able to refresh on long layovers. "Showering, grabbing a healthy meal, and catching a quick nap in a lounge makes me feel human again before boarding my next leg." Family traveler Sarah Chen appreciates having a peaceful oasis where kids can unwind on vacation journeys.

LoungeBuddy app users praise the ability to find and book access to 1,300+ lounges worldwide. User Helen Boyte gushes "My dream solo luxury experience is sipping champagne in a lounge before being pampered onboard Emirates First Class."

"Occasional lounge treats are sensible, but I couldn't justify $500+ a year as a deal-hunting budget traveler," he admits. Be choosey about which parts of your journey warrant the upgrade - say for an overnight layover between long-haul flights. For short hops, it may not be worth the spend.

Similarly, don't feel obligated to eat so much lounge food that you ruin your appetite for delicious local cuisine at your destination. As digital nomad Elise Blaha says, "I enjoy a pre-flight glass of wine in a lounge, but don't want to nullify my United Nations of food bucket list!"


Delays and cancellations spike over the holidays as weather disruptions and crowding stress airline operations. Veteran travelers like Jacobi advise packing supplies in your carry-on to stay nourished and sane if stranded for hours on end. Having non-perishable snacks, a refillable water bottle, battery packs, entertainment, and other essentials can transform potentially miserable experiences into minor inconveniences.

Digital nomad Elise Blaha always keeps a spare outfit, toiletries, phone charger, headphones, and Kindle in her personal item so she can freshen up and reboot if needed during travel snarls. She also packs high-protein snacks like beef jerky, nuts, and protein bars that offer lasting energy when her plans go off-track.
"Several Christmases ago, I got stuck sleeping overnight in the Las Vegas airport due to a snowstorm. But I made my 'stranded camp' under the USB ports and munched on snacks until the chaos passed," Blaha recounts.

Similarly, Helen Boyte recalls barely surviving a 13-hour delay in the New Delhi airport thanks to having electronics, scarf to use as blanket, and nuts and dried fruit on hand. "I even managed to nap on the floor using my purse as a pillow," she laughs. Her flight eventually resumed early the next morning.
Having a water bottle along is also crucial considering dehydration exacerbates travel headaches like jet lag, altitude adjustment, dry cabin air, and fatigue. The Patel family makes it a rule for each family member to carry a refillable bottle in their bags. "Kids inevitably get thirsty and antsy during delays. Having water prevents meltdowns and helps them power through," notes mom Tara Patel. They also pack healthy boiled snacks like bananas, applesauce pouches, and crackers.
For longer disruptions, a lightweight compression sack with sleep masks, earplugs, and neck pillows can make attempting rest more bearable. Noise-cancelling headphones drown out airport cacophony and maximize the escapism of movies, music, or podcasts. Pack playing cards, compact board games, or mad libs books to keep kids' minds engaged for hours on end.

If traveling as a couple or family, divvy up practical delay supplies between bags so no one is left empty-handed. Rhett Patterson suggests designating one person as the "electronics guardian" during travel to juggle battery packs and cable connections. Having backup chargers and adapters spread between multiple people safeguards against losing access.
While delays cause inevitable headaches, preparation minimizes the downsides. "I've come to accept disruptions as part of journeying," reflects Blaha. "As long as I have entertainment and some trail mix, I can withstand almost anything!" Building in buffers for possible misconnections is also wise when booking complicated itineraries.

See how everyone can now afford to fly Business Class and book 5 Star Hotels with Mighty Travels Premium! Get started for free.