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Optimize Your Next Flight: How I Book my Flights to Save Time, Money and Unlock Benefits

How I Book my Flights to Save Time, Money and Unlock Benefits

Continuing with last week’s theme, Maximize Your Next Hotel Stay: How to Optimize for Perks, Points & Unlock Other Secret Benefits, this week I go over the general thought process I use to book all of my flights.

I always want to optimize the value I am getting from my flights, whether it is in terms of overall cost, value of miles being used, or other perks like free bags, premium seat selection, or other promotions that may be available.

While you likely have many more options when booking accommodations/hotel, when it comes to flights, the options can be much more limited depending on where you’re flying from/to, as well as the airlines that fly those routes.

Since a majority of our flights are out of Sacramento (SMF), our options can be limited, so we don’t necessarily fly the same airline every time, we don’t have any airline loyalty program status earned through flying alone and don’t always book the cheapest fare we find (value schedule, prefer non-stops, award travel availability).

Based on our flying experience, here are the main things to consider when booking family trips for maximum value to optimize the perks you receive and unlock many other benefits:

Step 1: Start With Google Flights

Google Flights should be the first website you visit when you’re starting the process of booking an airline ticket.
  • Google Flights is great because it lets you compare fares across a wide variety of dates, allows fare tracking, and gives you all kinds of options to customize your search, which you won’t find when searching through an online travel agency or airline website.
  • You can customize your search by airline, cabin class,airline alliance partners, connections/nonstop, duration, price, departure/arrival time and other filter options. And if you don’t quite know where you want to go, the Explore tab is great for quickly finding prices on places you’re considering traveling to.

  • Once you figure out the best routes and airlines for your flight, the next step is to determine if it is better to pay cash or use miles if you have them for that airline or transferrable points from Chase, American Express, Capital One or other partners.
There are other similar websites that offer similar functionality, but I have found Google Flights to be the most intuitive, simplest and easiest to use, also its free. Other similar tools/websites include Flight Connections, Kayak and Hopper.

Step 2: Determine the Best Route & Airline

If you live in a relatively smaller city with an airport that may not have a lot of flight options and you’re not finding great flight options from the airport you plan on flying out of, consider the following options:
  • Determine if another airport close by would work and provide more options and value in the form of potential time or cost savings.
    • For our international flights, I always check SFO and LAX
  • Consider booking a positioning flight, which is basically flying from your current airport location to the airport where your primary itinerary begins.
    • For example, I may fly from Sacramento (SMF) into Los Angeles (LAX) first to get better pricing or award availability for flights that just aren’t available when flying out of Sacramento to my final destination. Or we may drive to SFO to get access to better flight availability and pricing.
I have booked positioning flights when flying to Europe, as options from the West Coast are much more limited when flying East and especially from my home airport of Sacramento.

  • Last Summer, we flew from Sacramento to New York City (SMF to JFK), spent a few days in New York City and then started our Europe trip by flying from New York to Paris (JFK to CDG) and back from London to San Francisco (LHR to SFO) using miles, which only cost me 26.5k miles per person, plus taxes/fees.
  • The total cost came out to 105k miles and $335 (taxes/fees and upgrade to premium economy seats) foru our family of four, but if I had to pay for these same exact seats it would have cost me ~$1200-$1500 per person.
By positioning my flights out of JFK to start with and knowing the routes and airlines partners that Delta had, I was able to save ~$4800-6000 on flights alone for this trip, which gave me a value of 4.5-5.7 cents per point, which is really good for Delta SkyMiles. Finding that type of award flight availability from SMF, SFO or LAX for Europe flights was pretty much impossible and I’d end up paying a lot of money for those flights.

Step 3: Always Book Direct with the Airline

  • Once you find the best route/airline and general pricing using Google Flights, I always recommend booking flights direct with the airline.
    • If you want to use airline miles, this is the only way to do so (I don’t recommend credit card travel portals if you want maximize value, see below for reasons why).
  • There is no reason to book through an online travel agency (Expedia,, Kayak, etc) or a travel advisor, as there is no such thing as a deal on just flights alone.
    • Airlines got rid of the commission structure for flights back in the late 1990’s and early 2000’s and there is typically no deal to be had when paying for flights, so tread carefully if you see an online website advertising lower fares than the airline direct.

Note: When packaging a flight with a hotel from an online travel agency (Costco, Expedia, etc) or through a travel advisor and wholesale travel suppliers they may have access to (Pleasant Holidays, Classic Vacations, Delta Vacations, ALG, and others) you may think you found cheaper airfare, but it is most likely an invisible rebate being given (from the overall commission) or that particular supplier may have a special relationship with certain airlines/hotel companies and can offer small discounts (likely from the hotel accommodation side).  Also, be sure to ensure the flight isn't a "Basic Economy" ticket that doesn't allow for advanced seat selection or other exclusions.

Also of note is that there are wholesale suppliers that only travel advisors have access to that can sometimes offer discounts on international airfare (SkyBird Travel, Regal Wings, Centrav), but from my experience it is not worth the time and potential headaches when/if you ever need support.

Step 4: Maximize Your Credit Card Perks & Benefits

Credit card perks and benefits for flights can include things like huge sign-up bonuses, access to yearly companion passes, free checked bags ($30+ savings per bag), seat upgrades, lounge access and more.
  • Examples of some of the perks offered by credit cards I currently have include:
    • Amex Platinum: 5x points on flights, Amex Centurion Lounge Access
    • Alaska Airlines Credit Card: Yearly companion pass, free checked bags
    • Amex Delta Platinum: Yearly companion pass, Save 15% off when booking award travel with miles, free checked bags
    • Chase Ritz Carlton Rewards Credit Card: $300 annual airline credit good for checked bag fees and other airline incidental charges

I don’t do anything special to accrue points and miles - I just put all spending I can on our credit cards to maximize the rewards we get and open some cards occasionally to maximize sign-up bonuses. If I am no longer flying a particular airline enough or am not getting any benefit from that airline credit card, I would just cancel it

I discussed some of the credit cards I use for travel rewards here: What's in my Wallet? How I Optimize my Travel Rewards and Save Big on Family Travel

Step 5: Other Things to Consider for Flights

  • Flight Preferences
    • Flight length: For flights under 5 to 6 hours, I generally book economy seats (sometimes paying a small miles upgrade or fee for premium economy) and for anything over that ranging from 7 to 10+ hours, I would be more inclined to try to book Premium Economy or Business Class, depending on price and/or award availability.
    • I always prefer flying non-stop to reduce layovers, chance of missed connections, avoid delays, try to lessen the chance of lost checked bags and get to our destination as fast as possible.
  • Checked Luggage Tracking
    • I started using Apple AirTags to track our checked luggage last year to avoid lost bags and knowing that my checked luggage made it onto the plane with us.
  • Do Your Research to Maximize Miles Value
    • Booking through a portal (Chase Travel Portal, Amex, or Capital One) can be an easy and quick straightforward way to use your points, but likely not the best use and value of points.
    • Harder to find good award availability (usually from an airlines hub) Delta has a dynamic awards chart, and some of its rates can be astronomically high
    • Learn about airline alliances (breakdown of the main airlines alliances coming soon)