032 | How to Fly a family of 5 to Hawaii for under $500?

Heidi walks us through their family's recent airline travel from Wisconsin to Hawaii and back for under $500. Through a combination of untourism, cheap flight spotting, and travel rewards she was able to optimize her family travel budget.

When price drives the travel strategy, start with these resources:

  • Generally speaking Heidi is a thrifty person who likes a good deal and has been traveling long enough to know her benchmark for a one-way domestic flight is about $100.  That is the price point she uses when determining when and where to travel and maintain their $2,500 yearly travel budget.  Most travel is determined by flight sales and the price points. 
  • If there are specific destinations in mind (such as cities with Major League Baseball stadiums), Heidi uses a subscription service called Scott’s Cheap Flights ($79/year) to track fare sales and mistake fares.  Scott’s Cheap Flights, through the premium version allows you to set up departure airports and specific destinations alerts and give you options.  There is a free version, however I have found the Premium version to be much more robust.  The average savings is $550 per ticket so the ROI is worth it.  If you are interested, use the link https://ordinarysherpa.com/scott to sign up and Ordinary Sherap will receive credit for the referral.  The service also highlights locations that she wouldn’t likely be aware of. 
  • Scott’s Cheap Flight is built on Google Flights, which is a great source to find cheap flights on all airlines.  SkyScanner is another option, but I use Google Flights for specific destinations and compare prices and schedules.  
  • Her total out of pocket flight related expenses were $228.48 for 5 people on 6 flights, baggadge, TSA PreCheck for 2 adults (kids under 12 are included with paid adult).  Airport Parking would add an additional $136 ($364.48 total) 
  • If you aren’t aware of Travel Rewards, Episode 018 Family Travel Rewards Tips with Melissa Lagerquist and Episode 019, Our Travel Rewards Strategy they would be helpful context and background.  

When a destination guides the travel strategy, use the following process:

  • When Hawaii came on her radar, she started to follow several airlines that were viable options.  United is not a preferred airline for Heidi, She loves Delta but their travel rewards program is not as family friendly.  Heidi’s top four were  Hwaiian Airlines, Alaskan Airlines, American Airlines and Southwest Airlines.  Southwest Airlines was the most travel rewards friendly and family friendly (more on that later).  
  • What airports have direct flights to your destination?  Having this information can help you design your itinerary and not let the airline choose that for you.  Direct Flights to Hawaii are most prevalent from the west coast (such as airports: SEA, PDX, SJC, BUR, LAX, BUR, SFO, OAK and possibly PHX, and LAS). Once you choose your airline, check the airline route maps to your desired destination.  Compare the direct route maps with Google Flights to see which airports had the cheapest direct flights. 

Why did we choose Southwest Airlines?  

  • Have open seating which means they do not assign seats. If travel with someone under the age 6, family boarding is between sections A & B.  You can pay an upgrade fee for section A seating.
  • 2 checked bags fly free per passenger.  The weight limit per checked baggage is 50 pounds so it’s better to have more bags that weigh less.  On most other airlines check baggage expenses are $40-$50 per flight.  
  • Southwest Airline uses Rapid Rewards (RR) as their travel rewards currency.  The redemption for number of rapid rewards is based on a cost per point equivalency.  In comparison many other airlines have a charts (ie minimum of  25,000 points = $250 flight) with Southwest some of your redemptions might be under 10,000 Rapid Rewards points.  See redemption chart below.  
  • No blackout dates for reward travel.  Given that her husband is a teacher this is really important since they don’t have flexible travel and most of the summer and holidays would typically be black out dates for other airline travel reward redemptions.  
  • Companion Pass is a premier travel rewards feature. 

What is Southwest Airlines Companion Pass?

  • The Dusek family has 5 people (2 adults and 3 kids between the ages of 5-11).  They operate in 2-player mode for travel rewards with both adults having their own credit cards, but they can transfer their rewards currency between family members
  • We plan our credit applications when we know we are going to have an increase spend.  
  • We now only use Travel Rewards credit cards (and got rid of all other credit cards such as Target, Costco, etc) and currently we each have 5 different credit cards active. 

Adult 1:

  • Chase SW Premier ($3,000 minimum spend in 3 months for 40,000 RR)
  • Chase SW Business Premier ($5,000 minimum spend in 3 mon for 60,000 RR)

$8,000 minimum spend would give a minimum of 8,000 RR + 100,000 RR from bonuses  (Note: many purchases are eligible for 2x-5x per $1 spent)

Adult 2: 

  • Chase SW Premier ($3,000 minimum spend in 3 months for 60,000 RR bonus )
  • Chase SW Performance Business ($5,000 minimum spend in 3 months of 80,000 RR bonus)

$8,000 minimum spend would give 8,000 RR + 140,000 Bonus RR (note: RR earned can be 2x on up based on the category of your spend) 

  • With 2 credit cards and 3 months (based on when he applied for the credit card) he had already achieved the 125,000 RR required in a calendar year to achieve Companion Pass
  • Companion Pass is earned when 125,000 RR are earned within a calendar year.  Once achieved it is good for the remainder of that calendar year, and the entire following calendar year.  
  • Sign up for SW Credit cards in October but don’t meet minimum spends for 2 cards until January and you will have 23 months on Companion Pass eligibility
  • Companion Pass allows you to have a companion fly with you for free an unlimited number of times.  You can change the companion 3 times in one year.  
  • Adult 1 has Child 1 as companion (free); Adult 2 has Child 2 as companion (free).  Adult 1, Adult 2 and Child 3 use the bank of Rapids Reward points to pay for their flights (plus September 11th security fees)

Hawaii Flight Itinerary with redemptions

  1. MKE – SJC:  (Adult 1, Adult 2, Child 3) (9,702 RR) + ($5.60)
  2. SJC – KOA Adult 1, Adult 2, Child 3 (10,764 RR) + ($5.60)
  3. ITO – HNL Adult 1, Adult 2, Child 3 (4,938 RR) + ($5.60)
  4. HNL – OGG Adult 1, Adult 2, Child 3 (4,938 RR) + ($5.60)
  5. OGG – LAX Adult 1, Adult 2, Child 3 (17,082 RR) + ($5.60)
  6. LAX – MKE Adult 1, Adult 2, Child 3 (12,744 RR) + ($5.60)

Companion 1 pay $5.60 per flight ($5.60 x 6 = $33.60)

Companion 2 pay $5.60 per flight ($5.60 x 6 = $33.60)

Total fees for Adult 1, Adult 2 and Child 3 ($16.80 x 6 = $100.80)

Total: $228.60 + 180,504 RR

Other tips to save on travel expenses and understand travel rewards:

  • Cheapest Flights are typically Tuesday or Saturdays
  • Southwest Airlines releases their itineraries 6 months in advance, many other airlines release routes 12 months in advance.  
  • You can continue to study this, but many of the redemption optimizations are not ideal for families.  Do what works for you!  Don’t stress about getting the best redemption rates.  
  • Southwest Airlines does not have many international flights
  • Use Chase Ultimate Rewards for Car rentals and Hotels.  TSA PreCheck is also a free benefit from our Chase Sapphire cards ($85 value for 5 years) Children under 12 can tag along with a TSA PreChecked parent.  
  • Use Capital One Venture for a travel eraser card to wipe out expenses for things such as Airbnb.

Resources listed during this episode: 

Downloadable strategy:https://ordinarysherpa.com/rewards/

Scott’s Cheap Flights: https://ordinarysherpa.com/scott

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