Rewards Points Travel

Step by Step to a Free Vacation

November 7, 2015

I thought it might be a fun idea, and hopefully useful for you guys to watch me start the process of getting a free vacation using credit card rewards points.  The steps provided below can apply to any vacation; not just the example trip I’m about to use.

First things first, to set expectations.  While it will take me maybe 20 mins to get my plan together for earning a free vacation, it will likely take me a couple months of regular spending with these cards to get the bonus rewards they offer.  In other words, I’m planning today for a vacation that I will take no sooner than 3-4 months from now.

Secondly, I feel obligated to put in a quick disclaimer for all of those that are shitty at paying bills:

  • Go to this site and learn as much as you possibly can about what activities can positively and negatively affect your credit score.  Do you have a hard time paying bills on time?  Is your rent sometimes a day or two late?  Do you ever simply forget to pay your cable bill on time even though you had more than enough in your account to cover it?  If this is you….DON’T get a credit card and definitely DO NOT get multiple.  The credit cards that have the best bonus rewards ALWAYS have the highest interest rates.  Usually around 25% or higher. If you miss one sizeable payment…you and your credit score will be screwed.

Alrighty, for those of you that are left…here we go!  I’m literally just going to make up a vacation I want to take after I finish writing this sentence.

Where do I want to go? : New York City

What time of year? : Fall

Where do I want to stay? : In a nice hotel in Time Square

Actually sounds pretty nice right? O.k., here we go!

Step 1: Google “Boise to New York flights”

  • The first result shows me a list of flights and airline carriers that will take me to New York City from my home town of Boise, ID.

Google Flight Search

Step 2: Google search to see if the airlines that can take me to New York City, have a rewards program.  Search Airline Name + Rewards.

  •  I started with a “Delta Airlines Rewards” google search since it was the first airline listed on my initial search’s results
  • The first search result was for the Delta Sky Miles program…which I clicked on.

Delta Sky Miles

Step 3: Find out what the current bonus rewards program is offering.

  • Looks like I’d get 50k bonus miles after spending $2k in 3 months.  I like it so far.

Sky Miles Offer

Step 4:  Find out how many miles I need to get a free round trip flight to New York.

  • I went to the “book rewards travel” link and typed in my origin (Boise) and destination (NYC) and kept my flying dates as “flexible”.
  • I actually found a pretty decent round trip flight from Boise to NYC, next September, for 50k miles which is exactly how much that credit card bonus off is for.  Who knew?!

Rewards Flights

So now I know that if I apply for this Delta Credit card and spend $2,000 in the first 3 months, I will get enough bonus points to fly round trip Boise to NYC FO FREE! (not counting the $25 or so in taxes I’d have to pay).
The same flight would have cost me over $500.  No thanks!

Boom! Free flight to NYC…done.  K, now I need to get a hotel.

Step 4:  Google search “Hotels in Time Square”

  • I found a few hotels I liked and then did a couple follow up Google searches with the “hotel name + rewards program”
  • After about 10 mins of snooping around hotel rewards program sites, I saw that the Hilton Hotel rewards program currently has a credit card bonus offer that would give me 2 Weekend Night Certificates if I spent $2500 on their card over 4 months.  Perfect for my trip to New York!

I now know that if I sign up for this Hilton Reserve Card, I will get 2 free weekend nights in a nice Time Square hotel in New York City!

Hilton Reserve Card

Well shit, that was easier than I thought.  I may actually do this. Ha.  Who doesn’t want to go to NYC for free in fall?  I could land, grab dinner and a Broadway show.  Maybe wake up early and go see the Statue of Liberty and Central Park before hitting up a Yankees game. …I digress.

So at this point you may be saying to yourself “that’s great and all, but how the hell am I going to spend $4500 in 4 months to get the rewards on those 2 cards to get this free trip?”

Once you put ALL of your monthly expenses on these cards (rent, car payment, utilities, gas, cell phone, groceries, EVERYTHING) it really isn’t as difficult as it seems.  According to recent statistics, the average person in the United States spends $1010 per month.

If you don’t have that many bills (which is awesome) then do 1 card at a time.  Start with the airline rewards card….earn the bonus.  Then get the hotel card and earn the bonus.  This will obviously take longer, but what’s the rush?  Start planning early.  My example trip above isn’t until September of 2016.  I would have PLENTY of time to hit those bonus rewards.

Another trick that Lacey and I use is the “buy one, get one” approach.  We pay for 1 vacation with the credit card(s) that will help us get our next vacation for free.

Well hopefully this is useful for anyone who wants/needs a free vacation.  Let me know if you have any questions as you start snooping around.  Good luck!


Some pics of our last trip to NYC since this post brought some memories back.

Empire State Building

Lacey in Time Square


Lacey New York City Skyline



4 Peeps liked this so far.

You Might Also Like

  • Chantelle November 7, 2015 at 7:38 pm

    Hey! So as Lacey may have told you, I am super intrigued by this practice. My only thought is, how do I pay rent or even my car payment with a credit card? Do you take out cash on the card?

    • ditchingnormal November 8, 2015 at 10:22 am

      Hey Chantelle,

      So paying your mortgage and car payment (specifically) with a credit card require a little more work since most banks don’t allow loans to be paid off with a credit card. Honestly, it’s a bit of a pain in the ass to set up, but can be done if you are struggling to hit a credit card’s spending requirement to get the bonus points.

      There are services online that you can sign up for like the Bluebird account, that help get around this issue. The Bluebird account is basically an online account you set up to pay your bills for you. It will mail checks to your mortgage company and whoever else you tell it to using the money you filled your Bluebird account with. You can add money to your Bluebird account using a DEBIT card. You can buy a prepaid debit card at Walmart/Target/Walgreens and other places using a credit card.

      I personally try to avoid doing this as much as possible unless we REALLY need help getting to a spending requirement. You might come to find…especially if you can put a spouses monthly expenses on the same card as yours…that your regular expenses (minus your mortgage bill and car payment) will be enough to hit these bonuses already.

      Also, business owners have a big advantage in the credit card game because you can use credit cards for every business expense you have. 🙂

      Let me know if you have any other questions!

  • Travel Prep Part 1 - Public Transportation | Ditching Normal | Lifestyle, Travel, Reviews February 6, 2016 at 2:25 pm

    […] so let’s say you’ve just arrived at your destination (by using our best practices for booking a free flight of course ? ).  When you walk off the plane and out those airport doors to a city you’ve […]

  • Anna March 10, 2016 at 12:00 pm

    A lot of reloadable prepaid debit cards no longer allow you to reload the card with a credit card. I know that’s the case with the Target Amex prepaid debit card. Which card do you use and is there a limit?


    • ditchingnormal March 10, 2016 at 12:49 pm

      Hi Anna!
      With all the changes lately regarding the reload cards, it’s getting really tough to do manufactured spending now. Lacey and I have just been focused on finding cards with low spending requirements and big bonuses to get our points. Cards like the current Hilton Surpass offer have 70k bonus points after spending $1k (and no annual fee). We put all of our bills on the card until we reach the bonus…then get a new card to repeat the process with.

      …one thing we haven’t tried, but have been curious about, is the possibility of paying a friend/spouse/whoever with a credit card using the Square App and then having them give you the money back via cash or check. So the money ultimately goes in a circle. There obviously would be the fee from the Square App (which is likely 2-3%), but it might be worth it to help get your bonus points faster. I need to do some more research on the legalities of a process like that, but the idea has been in the back of my head for a while now.

      Let us know if you have any new ideas!
      Thanks for reading Anna!