Last updated on April 11, 2022
The answer is…”not much.”
I love travel. I’ve missed not being able to travel over these last nine months, and by the time we’re able to travel again, it’s going to be well over a year.
A couple of years ago I got into travel hacking, which is basically just using credit cards to accumulate points towards free travel. A year ago I wrote a couple of posts on my old blog about what I was learning. You can check those out here if you’d like. It culminated in $8000 worth of travel to California and Hawaii for under $1000. Or at least it was supposed to culminate in that. COVID meant that trip was cancelled.
The good news is that I was able to get all of those points back, and then just sit back and wait until we could once again travel.
Southwest released their summer flights yesterday, and I was ready to pounce. I booked two awesome trips, and I thought I would lay out my process here.
The first trip I booked was a five night trip for Mandy and I to a Hilton all inclusive resort in Playa del Carmen. Using points that we had accumulated from using the AMEX Hilton credit cards, we paid 71,000 points per night, and the great thing with using points in Hilton’s system is that if you book four nights, you get the fifth free. So for 284,000 points and no fees, we’re staying there for five nights.
For airfare, we went with Southwest. Two years ago we qualified for the Southwest Companion pass after opening up two cards. We were supposed to be able to use the companion pass for two years, with it expiring at the end of 2020. Fortunately Southwest extended the expiration through June 30, 2020. So we booked one ticket for me for 27,000 Southwest points, and Mandy flies free (no points required due to the Companion Pass). There are fees/taxes when you book with points, and those fees/taxes jump when going international, so our all in total spent on this flight was $180.
The second trip I booked was two nights in Chicago for the whole family (I guess we need to include our kids a bit, right!). Non-stop flights to Chicago were 5700 points each way, so I spent a bit under 35,000 points for the boys and I to fly, and then used the companion pass for Mandy.
As for lodging, Mandy and I both had a free night due to having Hilton American Express cards. These were set to expire at the end of August, so we were trying to figure out the best way to use them. We opted for the Waldorf Astoria in Chicago. This bad boy goes for almost $500/night.
So here’s how the numbers break down…
Playa del Carmen Trip:
Two round trip tickets from Memphis to Cancun: $914.12
Five nights at the Hilton Playa del Carmen: $1799.35
Total: $2713.47
Actual amount spent: $180
Chicago Trip:
Four non-stop round trip tickets from Memphis to Chicago Midway: $671.84
Two nights at the Waldorf Astoria: $1113.73
Total: $1785.57
Actual amount spent: $33.60
So $4500 worth of travel for $214. I have to say that I’m pretty excited by that math!
Here’s the thing…this is doable for anyone. I have a business renovating houses which means that I might have more expenses than people who don’t, but it’s not necessary for travel hacking. I just put every possible bill and expense on whichever credit card I’m using at the moment. I wrote more on this in the already linked to blog posts, so I won’t repeat myself here.
If you’d like a place to begin, though, I recommend getting the Chase Sapphire Preferred card. It has a $95 annual fee. This is the card that I will probably never get rid of. Unless we have just gotten a new card and need to reach a certain spending to get the bonus, this is the card that we use for most purchases. The current promotion is that if you spend $4000 during the first three months, you get 100,000 Chase Ultimate Reward points. That’s good for $1250 worth of travel if redeemed through the Chase portal. These points can also be transferred 1:1 on a lot of partner sites, including Southwest. There are some other great perks with this card, one of which currently is a free DashPass membership from DoorDash.
Here is the link to sign up for a Chase Sapphire Preferred card. I have this here as a help to you, but Chase appreciates the referral so much that they give me some points. Yay!
The other card I would recommend at the moment is a Hilton Honors AMEX card. I love Hilton hotels, and getting one or two of these cards is a great way to get some awesome free travel. Here is a link that will take you to an option to choose between three cards. The link (which again, benefits both of us, so I’d truly appreciate you using if you’re going to apply!) will take you to one of the cards, but if you will select View all Cards with a Referral Offer at the top left of the screen, you’ll be taken to all three options. Here’s the breakdown.
Hilton Honors
100,000 points after spending $1000 during first three months
No annual fee
Complementary Silver status
Hilton Surpass
150,000 points after spending $3000 during first three months
$95 annual fee
Complementary Gold status
Free weekend night after you spend $15,000
Hilton Aspire
150,000 points after spending $4000 during first three months
$495 annual fee
Complementary Diamond status
$250 Hilton Resort Credit
Mandy had the Aspire card last year, and I had the Surpass card. At the time the bonuses were different. At this point the Aspire is probably not worth the high annual fee. Now I would go with the no annual fee one or the Surpass.
One last thing…there’s a good chance that getting on a plane won’t be the smartest move come June. The good news is that these trips are easy to cancel. Trips purchased with points are normally easier than those purchased with cash. One of the big reasons we booked these is that we had lots of time to cancel if needed.
I hope this is helpful, and if not, watch the video below and you’ll at least get a chuckle out of it. . Here’s to getting back to travel soon!