Booking A 10 Day Vacation With Our Points

Written by Dustin

In October, Kristin and I are taking a 10 day trip all on points and cash back. Where will be going, how will we get there, and where will we stay?

A few months ago, Kristin and I were trying to decide on where to travel to this fall, we had a few options in mind. Plus, since her vacation time couldn’t be rolled over to next year, we had to use it all. I know what a tragedy! 🙂 Places we discussed traveling to were:

  • Barcelona
  • Madrid
  • Munich
  • Berlin
  • Paris
  • London
  • Travel Domestically

Out of all those options, domestic travel seemed to be the least “sexy” choice. I mean last year, we went to Budapest and Prague, it was such an amazing time! Plus the amazing deals we’ve seen to Europe, it seemed like a no brainer.

After some discussion we actually decided to stay in the US and see more of what our own country has to offer. We will be spending 10 days traveling between Chicago, San Francisco, and San Diego. We are pretty excited since neither one of us has been to the West Coast.

So, how are we traveling there and what was our total cost?

Our Flights:

With some recent life changes, our airline of choice has changed. I’m not sure how I feel about it, but we will see how it works out!

For 2 legs of this trip, we will be flying Delta and the other 2 we will be flying Southwest.

Our flight itinerary will look like this BGR-ORD (3 days)MDW-SFO (4 days) SFO-SAN (3 days) SAN-BGR. I booked them all as one way tickets, to make things easier.

For booking our BGR-ORD and SAN-BGR, I used Delta miles. For our flights SFO-SAN, I used Southwest points. For my segments of MDW-SFO, I used different points for Southwest, I’ll explain below :-).

Booking BGR-ORD

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I intitally had this flight leaving BOS on Southwest, but some life changes had occured and it just made more sense to cancel that flight and book this one.

We had a few options for flights, including some that were 12,500 Delta miles, but those flights were later in the day. We wanted more time to explore Chicago, so we booked an earlier flight for 17,500 Delta miles + $5.60 per person.

The cost for that flight would have cost $735.20. It is not cheap flying from BGR!

I earned these miles from my Delta Gold card I opened when the bonus was 50,000 plus I had a $100 airline credit, which I used to buy a gift card for a future flight.

For this flight we were able to redeem our miles for just about 2 cents per mile. For a domestic ticket, I am very happy with that redemption!

Booking MDW- SFO

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For this part of our flight, I could have transferred Ultimate Reward points to Southwest, but I didnt….

Right around the time I was looking to book flights, my annual fee for both of our Citi Premier’s had come due. After some terrible retention offers, I needed to burn my Citi points. I was sitting on 52,630 points. After moving some points around with Citi, I was able to book.

After feeding my flights to Citi, they were able to book our flights to SFO (nonstop as well!)  for 25,276 Thank You points. Using these points saved us another $315. I am sure there were other ways to get more value from them, but needing to burn them ASAP and at 1.25 cents each on Southwest, I’ll gladly burn those before my precious Ultimate Reward points.

Booking through Citi Travel was extremely easy and painless. Although you can redeem your Thank You points for much more value than 1.25 cents per point. It made perfect sense to me to use them this way. And at the end of the day, this whole game is about using your points the way you want/need to make your travel goals happen!

On top of that, Kristin and I will each earn 803 Southwest points as well for this flight, worth about $12.85 each.

Booking SFO- SAN

At the time I was booking this segment of our trip, Southwest was having a sale it this flight was being offered for $59 one way, for a nonstop flight. The point cost was 3,006 points per person plus $5.60 in taxes and fees.

I still had points in my account to cover the cost of this segment! For a total of 6,012 points and $11.20, we were booked!

In what seems like a rarity for Southwest redemptions, we redeemed our Southwest points at 2.1 cents per point!

Booking SAN-BGR

I originally had used the rest of my Cit Thank You Points to book on Southwest. That plan changed and I needed to fly us back to BGR. I was able to cancel our flight on Southwest and actually have a credit worth about $340 for a future flight on Southwest. I love their free cancelation/rebooking policy.

For the flight home, I needed to use Delta again. Before I even looked I started to cringe at what the cost would cost us in points. I was very relieve when I saw there was award space at 12,500 Delta miles +$5.60 per person!

Screenshot 2016-09-10 at 5.16.37 PM

This flight would have cost us $545.20, this was somehow cheaper than flying BGR-ORD. I still had some Delta miles remaining from my bonus, but needed to transfer about 8,000 points over from American Express. This did cost about $5 to transfer points.

After taking into account taxes and fees, plus transfer cost, we redeemed our Delta miles for 2.1 cents per mile. For a domestic coach ticket, I am very satisfied with that.

Now let’s move onto our hotel accommodations!

Our Hotels:

Now I am a big fan of Hyatt, even more so since I have diamond status with them until February of next year. They are definitely my first choice, if possible! We are staying with family in San Francisco, so we did not need a hotel there. If we did, I would have booked at the Hyatt Centric Fisherman’s Wharf.

To make the Hyatt stays even better, the promotion they are running for earning 10% points back after stays, will mean I use even less points for this stay! I did account for the 10% rebate in my calculations below. Maybe if I’m lucky, I’ll be able to stack all the Hyatt promos and really earn some extra points!

Staying 3 nights in Chicago

Last year my wife and her best friend went to Chicago and we were able to get her a room at the Hyatt Centric. She really liked it and was happy to stay there again. I was sitting on my 2 free nights from the Hyatt Credit Card bonus and wanted to get max value from them.

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Ultimately, I decided on the Park Hyatt Chicago, since I knew I would get the most value from the free nights, plus it’s a Park Hyatt :-). I was able to book my 2 nights over the phones and  used  cash and points (12,500 points + $150). After booking room, I was able to use a suite upgrade for the night.

I was only able to use my suite upgrade (the suite was $1,000 a night!) on the night I used Cash and Points, not on the free night certificates (which I knew, but tried anyways). I did book it in a way though that I hope I am given the suite for 3 nights instead of 1.

I booked my Cash and Point stay for my first night, then the following 2 nights I will be using my free night certificates, I am hoping that since I will be in my room already Hyatt won’t have me move rooms during my stay.

My total for this stay, is 11,250 points, $150 , and 2 free nights certificates. The 2 free nights, currently, are getting us about $1,050 in value. If I am able to stay in the suite, it would move the value up to over $2,000 for the free nights

My point value for my redemption on my Cash and Points night is about 8.9 cents per point! That is an amazing value for Hyatt points!

Staying 3 nights in San Diego:

For this stay I was stuck between the Andaz San Diego or the Grand Hyatt. They both looked great, and I was leaning toward the Andaz, since there was a pool on the roof top. After some feedback on Twitter, I decided to book the Andaz San Diego.

Screenshot 2016-09-10 at 5.41.27 PM

Look at that roof top pool!

I could have spent 20,000 points a night , but that would have drained my Ultimate Reward account and I didn’t want to do that. I also had a suite upgrade I could use, so I had to book using Cash and Points for this stay to use the suite upgrade.

It cost a total of 27,000 Hyatt points and $375. We were upgraded to the Andaz suite which would have cost $1150 for the 3 nights. This means I was redeeming my Hyatt Points at 2.9 cents each. This is a number I am very happy with.

Now to make it even sweeter…..

If you noticed, I still need to pay (before taxes) $525 for my Hyatt stays. Even though I am happy for the value I am receiving on my points, I still would like that closer to $0.

Discover cashback is underrated and pretty fantastic, I feel it is almost not spoken about since it isn’t a sought after travel currency, but I think that is a mistake. That’s for a future post 🙂

When you redeem $90 in Discover Cash, you can redeem for a $100 Hyatt Gift Card. This is about 11% better than redeeming straight cash back, not to mention the fact you can earn 5% cash back on their rotating categories.

Since we still had some Discover Cash, I redeemed $450 in Discover Cash for $500 in Hyatt Gift Cards. This brings my actual cost of the hotels down to $25 before taxes.


Overall I spent a grand total of 123,526 points for this trip. It breaks down to 60,000 Delta Miles, 6,012 Southwest Points, 25,276 Citi Thank You Points, 38,250 Hyatt points, 2 Free night certificates, $450 Discover Cash and only about $50 of actual money for a 10 day trip!

If we paid for this vacation it would have cost us about $5,000 ($3,850 if you remove the free night certificate redemptions). Which means I received an value of about 4 cents per point this trip (or 2.9 cents per point if you remove the free night certificate redemptions).

What trips are you taking this fall courtesy of your points and miles? I never know if people want trip reports or not, so would you like to see trip reports from this trip?

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About the author


After completing 6 years of pharmacy school, I finally had the time to travel. I started investigating ways to travel for less and when I redeemed my first award flight for my honeymoon, I knew I was hooked! Fast forward a couple of years and places I had never dreamed of visiting like Budapest, Honolulu, Bermuda and many other places where all within my reach, and for little to no money out of my pocket. Now, I have collected well over a million points and miles, and try to help people travel for less on their wallet.


  • ‘Since we still had some Discover Cash, I redeemed $450 in Discover Cash for $500 in Hyatt Gift Cards. This brings my actual cost of the hotels down to $25 before taxes.’

    No. Discover cash can be directly moved to bank account 1:1 So you really saved $75 by using it for hyatt gift cards. 🙂

    • Hi Ruby,

      That’s great! Have a great trip! It always feel good when you can save a lot of money on traveling!