How to Find Cheap Flights to Hawaii: Expert Tips That Save Hundreds— Ep 69

Mastering the Art of Finding Cheap Flights to Hawaii

In this episode of Hawaii Travel Made Easy, Marcie, a Hawaii travel expert, shares her top strategies for finding affordable flights to Hawaii. Drawing from her experience of over 40 trips to Hawaii, Marcie provides insights into the best times to book, tools, and apps for tracking deals, and how to leverage points and miles for substantial savings. The episode covers peak, shoulder, and off-season travel tips, advanced booking strategies, common mistakes to avoid, and nuances, such as the effectiveness of last-minute deals and utilizing less crowded weekdays for cheaper flights. Additionally, Marcie discusses the role of credit card signup bonuses and travel consultations in optimizing flight costs, ensuring you can spend more on the unique experiences Hawaii has to offer.

00:00 Welcome to Hawaii Travel Made Easy
01:47 Timing Your Flight Booking for the Best Deals
02:45 Understanding Hawaii's Pricing Seasons
05:15 Tools and Apps for Tracking Flight Deals
09:05 Using Points and Miles for Hawaii Flights
13:54 Advanced Strategies for Extra Savings
16:40 Common Mistakes to Avoid
18:28 Your Action Plan for Booking Cheap Flights
20:14 Final Tips and Resources

Who this episode is for: Anyone wanting a comprehensive strategy for finding cheap Hawaii flights, beyond just the basic booking-window timing.

What you'll learn: How to time bookings across peak, shoulder, and off-season pricing, which tools and apps to use for tracking deals, how to leverage points and miles, advanced savings strategies, and common mistakes to avoid.

Activities discussed:

• Timing flight bookings across pricing seasons
• Using flight-tracking tools and apps
• Using points and miles for Hawaii flights
• Applying advanced savings strategies
• Using credit card signup bonuses

Marcie's recommendations:

• Time your booking around Hawaii's specific pricing seasons (peak, shoulder, off-season), not generic flight-booking advice
• Use dedicated tools and apps to track flight deals rather than checking manually
• Leverage points and miles for substantial savings when available
• Consider credit card signup bonuses as part of an overall flight savings strategy
• Apply advanced strategies for extra savings beyond the basics
• Avoid common mistakes that quietly inflate flight costs
• Use less crowded weekdays for cheaper fares
• Follow a clear action plan rather than researching without a system
• Get a travel consultation if you want help optimizing flight costs specifically

Related Hawaii Travel Made Easy episodes: 

• When to Book Your Hawaii Flight: The Sweet Spot Window— Ep 68
• Direct Flight vs Stopover: What East Coast Travelers Need to Know Before Booking— Ep 62
• Alaska & Hawaiian Airlines Merge - What Atmos Rewards Means for Hawaii Travelers— Ep 33

Related articles:

• The Hawaii Planning Guide Every Mom Needs: When to Book Everything from Flights to Fun
• How to Survive Long Flights to Hawaii with Kids: Secrets from a Parenting Pro
• Just Booked Your Hawaiian Flight? Here's What Every Mom Needs to Do Next
• 17 Hawaii Beach Essentials for Babies You Won't Regret Packing

Additional resources:

• Hawaii Travel Guides
• Free Email Planning Courses
• Etsy Shop

About Your Host: Marcie Cheung is a Certified Hawaii Destination Expert who has visited Hawaii 40+ times and spent 20+ years as a professional hula dancer. Through Hawaii Travel with Kids, she helps families plan authentic, affordable Hawaii vacations that respect local culture while creating unforgettable memories.

Learn more at hawaiitravelwithkids.com

Connect: @hawaiitravelwithkids on Instagram | Book a Consultation

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Transcript

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Aloha and welcome to Hawaii Travel Made Easy, your go-to resource for planning an unforgettable Hawaii vacation. I'm Marcie, and if you're new here, I'm a mom of two and a Hawaii travel expert. I've been to Hawaii more than 40 times, and one of the biggest questions I get is how do I find cheap flights to Hawaii and when should I book for the best price? And I totally get why finding discount flights to Hawaiian Islands is such a common concern. Flights are often the biggest expense for Hawaii trip. We're talking anywhere from $300 to $1,200 per person, depending on where you're flying from, when you're traveling, and how far in advance you book. If you can save even $200 per person on Hawaii airfare, that's $800 for a family of four that you can spend on experiences, better accommodations, or maybe even an extra day in Paradise. I've learned a lot about Hawaii flight booking strategies over my 40 plus trips, and I've also helped hundreds of families through my blog and social media save thousands of dollars on their Hawaii flight deals. Some have even gotten their flights completely free using points and miles, and I'm gonna share exactly how they did it. So today I'm sharing my most effective strategies for finding cheap flights to Hawaii at the best price. We'll cover the ideal timing for booking Hawaii flights, the best tools and apps to track Hawaii airfare deals, how to leverage airline miles and credit card points to get flights to Oahu and other Hawaiian islands for next to nothing. And some insider tricks that airlines don't necessarily want you to know about. Whether you're planning your first Hawaii trip or your repeat visitor looking for budget flights to Hawaiian Islands. This episode will help you get there for less, so you can spend more on the experiences that make Hawaii so special. Let's jump in. First, let's talk about timing specifically when to book flights to Hawaii for the best price and how to find the best Hawaii flight deals. Research consistently shows that the best time to book flights to Hawaii is typically between 40 and 70 days before departure. That gives airlines enough time to adjust pricing based on demand, but you're not booking so early that you're paying premium prices for the convenience of early booking. However, this sweet spot for Hawaii airfare deals changes dramatically based on when you're traveling for peak times, and I'm talking about Christmas and New Year's summer vacation, months of June through August and spring break periods March and April, you want a book as early as possible. I'm talking six to 12 months in advance for these periods. If you want cheap flights to Hawaii during peak season, I learned this lesson the hard way a few years ago when I waited until two months before Christmas to book our family's holiday flights to Maui, Hawaii. Flight prices had been $500 per person in January and were suddenly $900 per person, and that was for the least convenient times and route. Hawaii essentially has three pricing seasons that you need to understand for Hawaii flight deals. Peak season is mid-December through early January for the holidays, mid-June through August for summer vacation, and parts of March and April for spring break. During these times, you're looking at the highest Hawaii airfare prices and the most crowded conditions. Shoulder season, which is my favorite time to recommend for discount flights to Hawaiian Islands, includes the end of April, may, September, and October. Weather is still fantastic. Crowds are smaller, and Hawaii flight prices can be 30 to 50% lower than peak times. I found some incredible Hawaii travel savings during these months, especially in late September and early October off season Hawaii flights, which is really just parts of November and January through mid-March, excluding spring break weeks, offer the lowest prices, but potentially more variable weather. However, off season in Hawaii is still beautiful. It's not like you're visiting a ski resort in summer, so let me address something I get asked about a lot. Last minute Hawaii flight deals, while they do occasionally exist, they're increasingly rare for flights to Hawaiian islands. The days of showing up at the airport and finding cheap flights to Hawaii are largely over. Airlines have gotten much better at predicting demand, and Hawaii is such a popular destination that flights usually fill up rather than go empty. However, if you have complete flexibility, I'm talking about being able to leave tomorrow if a deal appears. You can occasionally find last minute fare drops when airlines need to fill empty seats. But here's my honest device, don't count on last minute. Hawaii flight deals. The risk of paying significantly more or not finding flights at all far outweighs the potential savings for most families. Here's a strategy that actually works for finding cheap flights to Hawaii. Be flexible about which days you fly. Tuesday and Wednesday departures are almost always cheaper than Friday and Sunday and flights to Honolulu and other Hawaii destinations. If you can shift your travel dates by even a day or two, you might save 100 to $200 per person on Hawaii airfare. I always tell families to look at their school calendar and work schedules to see if they can travel Tuesday to Tuesday instead of the traditional Friday to Friday pattern. Those weekend flights carry a premium because that's when most people want to travel. If you're flying from outside the us, the Hawaii flight booking timeline can be different. International flights to Hawaiian islands often need to be booked even further in advance, sometimes three to six months out for the best Hawaii flight deals. The routes are more limited in demand from international travelers has been growing significantly. Now, let's talk about some of the tools that will help you find and track the best cheap flights to Hawaii Deals Technology has made finding discount flights to Hawaiian Islands so much easier than it used to be. Google flights, is my absolute go-to tool for Hawaii flight planning, and it's completely free. Here's how to use it effectively for finding cheap flights to Hawaii. The calendar view feature is incredibly powerful for Hawaii flight deal. Instead of searching for specific dates, use the calendar to see Hawaii airfare pricing across entire months. You'll often find that shifting your trip by just a few days can save hundreds of dollars on flights to Honolulu and other places. The price tracking feature is essential for Hawaii travel savings. Once you find flights you're interested in set up price alerts, Google will email you when Hawaii flight prices drop, or if they're predicted to increase soon. I have clients who have saved $300 or more per person just by waiting for a price alert to tell them when to book Hawaii flights. The explore feature is amazing if you're flexible about which Hawaiian Island to visit. You can see pricing to all the islands at once. Sometimes discover that flying into Maui instead of Oahu or vice versa, saves significant money on your Hawaii airfare. Hopper is a mobile app that uses historical data to predict whether Hawaii flight prices will rise or drop. It will literally tell you to book now or wait. Prices are likely to drop. For your specific Hawaii flight deals, I found Hopper to be surprisingly accurate for flights to Hawaii, especially for popular departure cities like Los Angeles, San Francisco, and Seattle. The app learns patterns and can often predict Hawaii airfare movements with 90% accuracy. The app also shows you a calendar of the cheapest dates to fly to Hawaii, similar to Google Flights, but with their predictive element added in. Skyscanner is excellent for international travelers, or if you're looking at complex multi-city routes to Hawaii, their whole month and cheapest month features can uncover Hawaii flight deals that other sites miss. Kayak's price forecasting tool is similar to Hopper and can be useful for getting a second opinion on whether to book Hawaii flights or wait for better prices. Scott's Cheap Flights, which is now called going sends email alerts about flight deals including routes to Hawaii Islands, two Hawaiian islands, while you have to pay for premium features, their free tier still catches major Hawaii airline deals. Don't forget to check airline websites directly, especially Hawaiian Airlines, Alaska Airlines and Southwest for flights to Honolulu and other places. They sometimes offer Hawaii flight deals that don't appear on third party sites, and you'll avoid any booking fees. Hawaiian Airlines Fair Calendar is particularly useful for Hawaii travel savings. It shows our lowest fares for entire months at a glance. Southwest low-fare calendar is also excellent for finding cheap flights to Hawaii, though they don't always appear in third party search engines. Okay, so here's how to set up a comprehensive alert system for Hawaii flight deals. Use Google Flights for your primary alerts hopper for their predictions and sign up for airline newsletters for flash sales, set alerts for multiple date ranges, maybe your ideal dates, plus a few days on either side. But don't go overboard. I've seen people set up so many alerts that they get overwhelmed and miss the actual good Hawaii flight deals. Focus on your most likely travel dates and maybe one or two alternatives. Okay, so you've probably heard you should search for flights in incognito mode. To avoid Hawaii flight price increases. While this was possibly true years ago, most experts now agree it's largely a myth. Airlines are sophisticated enough. That your search history isn't significantly affecting the Hawaii airfare prices You see? That said, it doesn't hurt to clear your cookies occasionally, and incognito mode can help you avoid the psychological pressure of seeing Hawaii flight prices that seem to be increasing artificially. Now, let's talk about my favorite way to book flights to Hawaii using points and miles. This is honestly where you can see the most dramatic Hawaii travel savings. Sometimes getting flights that would cost $800 or more just for taxes and fees. The Points and Miles game has changed significantly in recent years. Airlines have mostly moved away from distance-based awards to dynamic pricing, which means award prices for flights to Hawaii fluctuate based on demand, just like paid fairs. But there are still incredible opportunities for Hawaii flight deals if you know how to play the game. Alaska Airlines and Hawaiian Airlines merged recently, and they now have Atmos rewards. I have a whole podcast episode about that, that you should take a listen to if you're interested. These are great for flights to Hawaii, especially if you live on the West coast. They have a companion fair, which means that you buy one ticket and your companion flies for just taxes and fees, which is usually around $22. Southwest Rapid Rewards is excellent for families because their companion pass, which you can earn by flying a lot or getting their credit cards means one person flies free for almost two years. Southwest also has no change fees, which is huge for family travel flexibility when booking flights to Hawaii. United American and Delta all offer Hawaii Award flights. Though pricing can be unpredictable, the advantage is that these airlines have more frequent sales and broader route networks for flights to Honolulu and other places. If you're looking for credit cards, chase Sapphire Preferred or Reserve cards earn ultimate rewards points that transfer to United Airlines, which has extensive Hawaii service. The signup bonuses on these cards can often cover an entire Hawaii trip for two people. American Express membership rewards transfer to Delta and Hawaiian. Their personal and business cards often have lucrative signup bonuses for earning points toward Hawaii flights. Capital One Venture and Venture one Cards earn miles that can be used to cover any travel purchase, including flights to Hawaii. This is great if you want flexibility and don't wanna deal with airline award charts. Now let's talk about the signup bonus strategy for Hawaii savings. Here's where you can really win big with cheap fights to Hawaii credit card signup bonuses. Many travel credit cards offer 50,000 to a hundred thousand or more bonus points or miles when you meet spending requirements. That's often enough for one or two round trip tickets to Hawaii. But please, and I cannot stress this enough. Only do this. If you can meet the spending requirements with money you would spend already and only if you can pay off the balance immediately. Credit card interests will quickly wipe out any Hawaii travel savings from free flights. I recommend booking award flights to Hawaii as early as possible. Many airlines release award space 11 months in advance. Hawaii award seats disappear quickly, especially during peak travel times. Be flexible with your dates and routing for flights to Hawaii. Sometimes flying Monday to Monday instead of Friday to Friday can mean the difference between finding award space or not. Consider mixing cabin bookings for your Hawaii flights, maybe book economy on the way there, and first class on the way back, or vice versa if that's where the award availability is. Use tools like Award Hacker to see how many miles you need across different programs per flights to Hawaiian Islands. An expert flyer are often more flexible than airline miles because you can transfer them to multiple airline partners. For example, chase Ultimate Rewards transfer to United, Southwest and many other partners. So you can choose the best value for Hawaii flights. When you're ready to book, however, don't transfer points until you're ready to book flights to Hawaii. Once you transfer points to an airline, they're stuck there and subject to that airline's award chart and availability. Many airlines now offer the option to pay with a combination of cash and points for flights to Hawaii. This can be great when you don't have quite enough points for a free Hawaii flight, but want to use some points to reduce the cash cost. Finding the best flight deals and maximizing points and miles requires constant monitoring and quick decision making. It's honestly a part-time job if you really wanna do it well. Well, I can't book flights for you directly. My Hawaii travel consultations help you create a comprehensive flight strategy that saves you time and money in a 60 minute session for $149. We'll set up your tracking systems, identify your best points, miles options, create a booking timeline, and discuss strategies specific to your departure city and travel dates. And because you're working with me, my travel agent partner waives her planning fee for your trip. So Kim at Stuffed Suitcase will handle booking your accommodations and activities once you've secured your flights. If you've already booked flights and wanna make sure the rest of your trip is optimized around them, or you just need quick advice on a specific flight decision, a 30 minute consultation for $69 provides focus, support. Head to Hawaii, travel with kids.com to book and let's create a complete Hawaii travel strategy that saves you money from flights to activities. Now let me share some advanced strategies that can help you save even more on cheap flights to Hawaii. Sometimes flying into a different Hawaiian island than your final destination can save significant money. For example, if you wanna visit Maui, check flights to Honolulu too. The inter island flight might cost 80 to $150, but if you save $300 on your mainland flight, it's worth it for overall Hawaii travel savings. This works the other way too. Sometimes flights to Maui or flights to the big island have better deals than flights to Honolulu, even if Honolulu is more convenient for you. On the departure side, consider nearby airports or finding cheap flights to Hawaii. If you live in Northern California, compare San Francisco, Oakland, and San Jose. If you're in Southern California, check Los Angeles, long Beach, Burbank and Orange County. The drive might be worth hundreds in Hawaii Air fair savings. You might have heard about Hidden City ticketing. That's booking a flight to a destination beyond Hawaii with a layover in Hawaii, and then just not taking the final segment. While this can save money on Hawaii airfare, I have to strongly advise against it for several reasons. Airlines can penalize you. It only works for one-way flights and it can cause problems with your return flight. The savings aren't worth the risk for most travelers seeking cheap flights to Hawaii. Occasionally, airlines make pricing mistakes that result in dramatically discounted fares from flights to Hawaii discounted faires for flights to Hawaiian islands. While these are rare and unpredictable following accounts like secret flying or going can help you catch them when they happen. However, don't plan your Hawaii vacation around hoping for an error fee. Treat them as a nice surprise if they happen. Flight and hotel packages for Hawaii can sometimes offer savings, but more often they don't. The pricing is often opaque, making it hard to compare, and you lose flexibility. I generally recommend booking Hawaii flights and hotels separately unless you find a package yield that's clearly better than individual bookings. Costco's usually great for that. Some credit cards offer bonus points for airline purchases. If you're booking paid flights to Hawaiian Islands, using a card that earns two to three times points on airline purchases can help you earn points towards future Hawaii travel if you fly frequently enough to earn airline status. The benefits for flights to Hawaii can be significant. Free checked bags, which is huge for beach vacation packing, potential upgrades to first class and priority boarding. However, don't choose flights based solely on earning status unless you're already very close to qualifying. Some airlines allow stopovers longer than 24 hours in their hub cities without additional charges. For example, you might be able to stop in Los Angeles or Seattle for a few days on your way to Hawaii without paying extra. This isn't common anymore, but it's worth checking if you wanna visit multiple destinations. Okay, now let me share some common mistakes I see people make when looking for cheap flight to Hawaii so you can avoid them. The biggest mistake I see is when people wait too long to book peak season. Travel to Hawaii. If you wanna be in Hawaii for Christmas. New Year's ordering summer vacation book as early as airlines allow, often 11 months in advance. I've seen families pay double for Hawaii airfare because they waited until a few months before travel. Don't just look at Hawaii flight prices in isolation. Sometimes a slightly more expensive flight gets you there at a better time. Saves hotel nights or avoids expensive last minute accommodation bookings. Look at your total Hawaii travel cost, not just airfare. Many airlines now offer basic economy fairs that can be significantly cheaper, but come with restrictions like no seat selection, no changes allowed boarding. Last, make sure you understand what you're buying for your flights to Hawaii Islands, especially for family travel when sitting together matters. Also factor in baggage fees when comparing airlines for Hawaii flights, Hawaiian Airlines includes one check bag on mainland routes, while many others charge 30 to $35 each way. For a family of four flying to Hawaii, that's potentially 240 to $280 in additional fees. Always understand change cancellation policies before booking flights to Hawaii. While airlines have become more flexible since 2020, policies vary significantly between airlines and fair types. Trip insurance might be worth considering for expensive Hawaii flights, or if you have big concerns about needing to change plans. If you're booking for a family, try to book everyone on the same reservation when possible for flights to Hawaii. This makes changes easier and often ensures you can sit together. However, sometimes booking individually can save money on Hawaii airfare. You just need to weigh convenience versus cost. All right. Let's wrap up with your action plan for finding the best cheap flights to Hawaii. First, determine your travel flexibility for Hawaii flights. If you have fixed dates, start monitoring Hawaii, airfare prices as early as possible, and book when you find good Hawaii flight deals. If you're flexible, use that flexibility as your biggest advantage. Flexible travelers can save hundreds of dollars on flights to Hawaii. Set up price tracking on Google Flights and Hopper for your preferred dates and a few alternatives. Don't overthink this set up alerts and let technology work for you to find Hawaii travel savings. Consider whether points and miles make sense for your situation. If you're planning six to 12 months ahead, you can responsibly use credit cards to earn signup bonuses. This can provide enormous value for flights to Hawaii if you're traveling during peak season, which is Christmas, summer, spring break to Hawaii, start looking nine to 12 months in advance and book when you find good Hawaii flight deals for shoulder season travel to Hawaii. Start looking three to four months ahead and book when prices hit that 40 to 70 day sweet spot. Or when you find Hawaii airfare deals you're happy with. For off season travel to Hawaii, you can often wait until 30 to 60 days out, but earlier is still generally better for cheap flights to Hawaii. Remember that perfect Hawaii flight deal might not exist. If you find flights at a price you're comfortable with that fits your schedule, book them and stop looking. The stress of constantly price checking can overshadow the savings. Consider the total value of your Hawaii trip. Saving $100 on flights, but missing a day of vacation because of poor flight times, might not be worth it. Most importantly, don't let Hawaii flight prices stop you from taking your Hawaii vacation. Yes, save money when you can, but remember that you're investing in experiences and memories that will last a lifetime. I've put together additional resources on my website at Hawaii Travel with kids.com. Including guides for using specific airline miles, airline mile programs, and credit card strategies for Hawaii Travel. If you have specific questions about your situation, feel free to reach out on Instagram at Hawaii Travel with Kids. I love helping families plan their perfect Hawaii trips and find the best Hawaii flight deals. If this episode was helpful, please subscribe to the podcast and leave a review. It really helps other travelers find this information about cheap flights to Hawaii and more subscribers means I can continue creating helpful content about Hawaii travel. Mahalo for listening, and I hope these strategies help you get to Hawaii for less, so you can spend more on the experiences that make Hawaii so magical. Until next time, aloha.