How I planned a luxury vacation to Hawaii for less than half the price

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For four people, two weeks, the average Hawaiian vacation costs over $8,600. Some estimates I found put the average cost closer to $24,120!!

How much did I spend? $2,825

How did I plan a Hawaiian vacation so cheap? I’ll break it down for you.

Flights $1,600

Hotel $200

Rental Car $720

Activities $130

Food/eating out $550 (-$375 that we would normally spend at home in 2 weeks)

Total cost of entire Maui vacation $2,825

Scroll down to see how I got that price for each category!

Planning a family vacation to Hawaii for cheap

Our family vacation time is precious to me. I’m a nurse and work long shifts, which means I can be more flexible in my schedule. But my husband has your typical 8 to 5, Monday through Friday schedule. He only gets so many vacation days a year, so we have to prioritize our travel.

Imagine six-month pregnant me. GIANT belly. Super sick, throwing up every day. Working through a pandemic as a nurse. Wild three-year-old at home.

Then my husband drops this bombshell,

“I have to use my vacation days for paternity leave”.

I was crank-ky! But after sulking for a few days, I decided that if he had to use vacation time…we might as well go on vacation after the baby was born.

It needed to be somewhere that would be relaxing, low key, no pressure to do lots activities, but opportunities to play outside for my toddler. And we wouldn’t have a passport for baby, so it had to be in the US.

Hawaii was perfect.

Except Hawaii is one of the most expensive vacations that you can take. And I wanted two things:

1. I wanted to get the vacation for cheap.
2. I wanted it be a nice vacation. A beach front hotel, with a pool, a separate bedroom and a full-sized kitchen. Plenty of time to relax and take it easy after having a baby.

So, I got to work.

Finding a cheap flight to Hawaii

$400 each, $1,600 total for 5 tickets (yes you read that right)

This is the longest part of the trip cost breakdown, but it’s really cool so stay with me here.

Usually, flights are the most expensive part of a vacation. Therefore, they are often where I start looking for travel deals.

If I can quickly and easily save a few $1,000 by saving on big ticket items, then I stress less about looking for deals on less expensive parts of a vacation (like activities and eating out).

I wanted direct flights that flew during good times of the day. Challenge accepted.

What makes flights to Hawaii so expensive?

Normal flights to Hawaii can cost up to $1,000 each, assuming you fly economy. First and business class can go up to $4,000 a ticket!

There are certain factors that can make the tickets more expensive. Going in the prime travel season (the most popular times of year to travel to Hawaii). Direct flights. Ideal times of day to fly.

There was no way I was going to pay that much for plane tickets to anywhere. But I was determined to go to Hawaii. So, I had to figure out another way.

Here’s how I found a deal on airfare to Hawaii

I subscribe to a few flight finder sites that look for flight deals I may be interested and send them to me (read more about the 4 best free ones here. My favorite is Scott’s Cheap Flights you can try them for free considering using my promo code if you do).

I knew a good flight deal for Hawaii was between $300 to $550 roundtrip.

We were going in prime travel season for Hawaii, so I knew the flight prices might be on the higher end of that range.

Once I knew what a good ticket price would be, I went to Skyscanner.com.

Skyscanner lets you look at the best flight prices for an entire month at once. It also searches (almost) all the airlines at the same time for the best prices.

This is a great feature to find flight deals because you can easily see what days are the cheapest to travel. Sometimes changing your travel plans by one day can save you $100’s per ticket.

First, I gave myself four weeks after my due date, in case of complications with the baby, and found the cheapest days around that time for us to fly out.

Next, I double checked at Kayak.com (another online booking site that checks all the airlines at once) to see if they had cheaper tickets.

Finally, I went to Southwest airlines site directly and checked the prices there since they fly to Hawaii and Southwest doesn’t show up on the online booking sites.

The cheapest tickets were with United for $350 but had a very long layover both ways and left at awkward times. For $400, I still had a layover both ways but they were shorter and flight times better.

You could upgrade the ticket and pay more for seat selection, more baggage and changeable tickets. But I booked the basic fare for me, my husband, my toddler and my brother-in-law.

You can’t buy a ticket for an unborn baby, so I had three options.

1. Wait for her to be born and buy her ticket separate at a higher price. That way she is guaranteed a seat on the plane.
2. Wait for her to be born and add her as a lap infant for free. But I’d have to hold her the entire flight.
3. OR get her own seat for FREE at the airport. Then, I can bring her car seat on board and have her sleep in it…

So let’s take count of what I have so far:

I wanted direct flights for all 5 of us with good departure/arrival times for a great price.

Right now, I have 4 flights with a layover each way, ok times, and a great price.

I was ok with what I had ($1,600 is so much better than $4,000), but I had a few tricks to switch to the tickets I wanted…for free.

How I got upgraded to the flight I wanted for free

A few weeks later I got an email that there was a change to my flight itinerary. My flight to Hawaii was going to depart an hour later now.

This flight delay might be frustrating to some travelers, but it’s super exciting to me!

It’s significant of enough change that, per United’s policy, I am entitled to a free flight change or cancellation. No matter the ticket I booked, even the cheapest no change flights.

So first, I search Google Flights for flights from Denver to Maui and set the filter to direct flights AND with United and all of United Airlines flight partners (Star Alliance).  Then, I find my ideal flights I want, write down the flight numbers and give customer service a call.

Next, I tell the agent that my flight time was changed and I needed to change it. She tried to move me to the flight with the even longer layover, but I told her I needed to be moved to flight number xyz. And she makes the flight change for me. No charges.

Now I have my ideal flight to Hawaii direct with times I want. My flight back still has a layover.

A week after the baby is born, I get another email from United.

“One or more of your flights is full and social distancing may not be possible. If you need to make changes please let us know and we’ll be happy to accommodate you.” I call back customer service, add the baby as a lap infant for free and change my flight back home to the direct flight I want. Again, all for free.

Now I have the flights I wanted both ways (normally would have been $4,000) for $1,600.

But the baby is still a lap infant, and I want her to have her own seat so we could bring her car seat on board with us.

Changing a lap infant flight to a free seat

This may be a no brainer to you, but I have found this trick to be super helpful to lots of traveling parents. It’s a really easy way to get your lap infant a free seat for the plane.

Once you get to the airport, check in and get through security and to your gate.

Then, when the gate agent arrives go up and nicely ask if your seat assignment can be moved to be near an empty seat. If there is one available, I’ve always had them accommodate us.

Boom. Now you have another seat for free. It’s so helpful to have the extra space when traveling with kids!

Now we have $5,000 worth of tickets for $1,600.

How long did it take me to find a cheap flights to Hawaii?

Often people assume that if you want to find travel deals, you have to spend a lot of time looking for them.

How long did it take me to save $3,400 on flights? About three hours (and honestly two of those was cleaning my house while being on hold for customer service).

Finding a cheap ocean front hotel in Hawaii

$200

When I say I travel for cheap, I mean the price. I never mean cutting out the things in your vacation that are important to you.

For this vacation I specific things I wanted in a hotel in Hawaii.

• Ocean front or less than 5 minute walk to beach
• Outdoor pool
• Separate bedroom
• Full sized kitchen
• In-suite washer and dryer
• Two bathrooms (since my brother-in-law was coming also)
• And it had to be nice inside

Most of the hotels I was finding with all that were between $300-$500 a night, or $4,400 – $7,000 for the two weeks we’d be there! Nooope.

There’s a handful of ways I will look for deals on a hotel, but this time I knew I had a bunch of points on my travel credit card that I could use.

I always put all my charges on a travel credit card and pay it off each month. That way each dollar I spend in normal life, gives me points to a free vacation. (There’s lots of other perks to using a travel credit card, read more here.)

My travel credit card was running a promo where if I booked a hotel through their portal and paid for it using the card, I’d get 2x points. I wanted to use points not money for the hotel, but I also wanted to take advantage of this promotion.

How to both use AND earn travel credit card points on a vacation

Usually, if you choose to redeem points to pay for your vacation, you don’t earn points on that purchase like you would if you had paid for those expenses on your card.

Makes sense, right?

My current travel credit card is the Capital One Venture Card. I love it for lots of reasons but one is that you can use your points to refund your card on eligible travel purchases. (If you decide you want to get this card, consider using my referral code here.)

First, I booked the hotel I wanted through the credit card portal using their credit card. Boom. Earned 2x points on that purchase.

Secondly, I waited for that billing cycle to end so the 2x points would be added to my account.

Then, I requested a refund on the cost of my hotel through points and the hotel cost was reimbursed back to my card in a few days.

When we got to the hotel, I paid $200 worth of resort fees as my total hotel cost.

How I got a rental car in Hawaii for cheap

$720

Normally, a rental car is like an afterthought. You get it after you pay the other big expenses of a vacation, like flights and hotel.

But right now, there’s a rental car shortage, and they are expensive. The car size I needed was running between $80-$100 a day, or $1,120-$1,400 for our trip. Woah!

**(I recently shared in my newsletter all the different ways to easily find a good deal on a rental car. If you aren’t on my email newsletter list and would like to, you can sign up here. I always give out my best tips there.)

Get ALL the best family travel hacks

Here’s how I got a cheap rental car in Maui.

First, use an online booking site that searches all the different rental car agencies at once. I like to use Kayak.com.

Second, when you are adding your details change the pickup/drop-off location from the airport to the city you are landing in.

Why? There are certain airport charges and taxes that have to be added to rental cars from an airport location. Also, rental companies know that people will pay more for the convenience of being able to pick up and leave the car right at the airport.

So instead, reserve your car near but not at the airport. I found a bunch of major rental car agencies less than 3 miles away for a third of the price.

Then, take a Lyft or Uber to pick up your car (bonus: some travel credit cards have free monthly ride share credits and will reimburse you for this).

I made an Instagram reel of how to do this you can see and save here. (BTW follow me on IG if you want more travel hacking tips!)

But I made a major mistake here…

I found the deal. And then I waited.

Ugh. I knew I should have reserved the car then but didn’t and the price went up when I checked again. *face palm*

$500 turned into $720. But still better than the $1,200 plus!

How to find deals on activities in Hawaii

$130

I have lots of awesome tips to save on activities when traveling. But honestly for this vacation I wasn’t up for a lot of activities…I just had a baby!

We just wanted to swim, play at the beach and relax. That’s what Hawaii is all about.

Week two I was feeling more up for adventure so we started doing more things. I found some great deals on the Maui Ocean Center Aquarium, snorkel gear and other activities by:

• Using Groupon.com or Livingsocial.com
• Finding bundled activity deals (ex. Surf shops that also will throw in snorkel gear for free if you sign up for a class)
• Simply googling for coupons/discounts

Our favorite thing was to drive the Road to Hana and check out all the waterfalls and banana bread stands along the way. You feel like you’re driving through Jurassic Park!

How to eat for cheap in Hawaii

($550-$375 we normally spend at home) = $175

I didn’t keep super close track of how much we spent on food this trip. But this is pretty close.

I LOVE eating out when traveling, but eating out three meals a day adds up fast. Plus, I do get tired of eating out after too much of it.

Save on food in Maui trick #1

Eat at least one meal at the hotel. We probably made our own food an average two meals a day.

Breakfast is the best for this. Some places will even include it for free, but usually resorts don’t. Paying more for a hotel with a kitchen or kitchenette (minifidge and/or microwave) may end up saving you more in the long run!

Since Hawaii is one of the most remote locations in the world. Almost everything has to be shipped a long way to get there, including food. This means groceries are really expensive in Hawaii! Soooo…

Eating in Hawaii for cheap trick #2

Shop where the locals shop. The more touristy the area, the more expensive everything will be. Especially groceries.

I did a little research before and then asked locals when we arrived to find the best grocery stores to shops and favorite restaurants. And everyone’s recommendation…Costco.

Prices were better than any of the smaller grocery stores and it was easy to stock up for the week.

Finally trick #3 for cheap food in Hawaii

Embrace food trucks, street food, and even the ABC store (their drug store) spam musubi. The meals are much cheaper than sit down restaurants and really fun to go to!

Flights, hotel, rental car, activities, food. All the parts of a dream vacation for most people rolled up into a cheap happy package.

Do you feel encouraged that you could afford to go on your own amazing Hawaiian vacation?

Not only can you book it for cheap, but the whole process of looking for the travel deals took about 4 hours total.

I used to feel discouraged reading travel hackers’ stories about how they were able to book dream vacations in extremely complicated ways. It was cool to hear about, but so overwhelming!

The most exciting thing to me is that now that I know how to find my own travel deals. It feels really easy, I know I can do it again and again!

Years ago, I thought this kind of vacation would be impossible. But it wasn’t even close to the best deal I’ve found.

And here’s the kicker….

These steps worked for this trip, but it won’t for every trip.

What if you don’t have credit card points, or know how to look for hotel deals, or the loopholes that help you get free flights and upgrades??

Every trip is unique and if you have any questions or want help planning your own dream vacation for cheap…let me know, I’d love to help!

Send me an email (kelli@tripfixers.com), DM me on Instagram or…

If you’re ready to start with 1:1 help planning your vacation check out my coaching here.

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