Hey Swifties, this one’s for you – My Taylor Swift Concert Experience

Making Dreams Come True with Points and Miles

by Sash
a wall with a sign on it

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In the Points and Miles realm, I usually highlight the aspirational side of travel:  the first-class flights, 5-star hotels, fine champagnes, etc., but I rarely talk about the unique experiences that can be made possible with the help of points and miles, which would otherwise be unattainable.

This is a story of how I was able to treat my daughter (Zoe) to the most unique experience of her life, a Taylor Swift concert. It might be the most significant accomplishment after a decade of earning and burning points. It goes a little something like this:

Me: “Let’s listen to something else, Zoe.”
Zoe: “No, Dad, put on Taylor Swift.”
Me: “But it’s been six months now, and it’s all we ever listen to in the car!”
Zoe: “So, what’s wrong with that?”
Me: “I’m tired of it; please listen to something else?”
Zoe: “No!”

This has been the ongoing dialogue between Zoe and I for the past year. Yes, that’s right, a year! I’m sick and tired of repeatedly listening to Taylor Swift’s songs in the car. Then, when my wife is also in the car, it’s a double whammy with both of them singing; torture is an understatement.

The Idea

One day in October 2022,  Zoe started playing new songs that I’ve never heard before. It was so refreshing not to listen to the same songs repeatedly. A new album was released? Less than a month later, on November 1, 2022, I caught wind of a concert tour that Taylor Swift was putting on in 2023 across the United States. Note, I do not follow Taylor Swift on Twitter.

Taylor Swift Concert

Concert Announcement, source: Twitter

Fortunately, my love for Zoe is stronger than my hatred of Taylor Swift, so I thought to myself how special it would be if my wife and I took Zoe to experience her first concert to watch her idol perform, on stage, live, in front of thousands of other “Swifties” just like her. Also, the concert date could nearly coincide with her birthday in June. The idea seemed quite outlandish to spoil her like this. Regardless, I pitched the idea to my wife, who agreed that although this would spoil her, it would be an experience she would never forget. Then she told me, “Find out first if you can get tickets.” I had no idea what the big deal was in buying tickets until later.

Buying Taylor Swift Concert Tickets

I was naïve and did not realize the kind of demand for tickets a Taylor Swift concert could generate. Luckily, my friend Rachel reminded me that Capital One cardholders would have access to presale tickets. I had acquired a Capital One Venture X Visa card about a year prior, so I could leverage this to access the presale tickets; brilliant!

a close-up of a sign

source: godsavethepoints.com

I had about a week before the presale tickets would go on sale, and I had to figure out which city we would travel to for the concert. I use only one criteria to determine this: which cities have direct flights from Ottawa? The answer was New York, Chicago, and Washington. New York would be my first choice, followed by Chicago.

a map of the world

created using gcmap.com

I then spent hours analyzing the stadium charts to try and determine the section I would want to book that would have the best bang for the buck. I took notes so that I would be prepared when the tickets would go on sale.

a seating plan of a stadium a seating chart of a stadium

Stadium Charts from cheaptickets.com

Then, on November 16, I logged onto Ticketmaster, and after some time in queue, I managed to purchase the tickets for the concert in Chicago on June 4, 2023.

Taylor Swift Concert

Then, two days later, on November 18, news broke of how all concert tickets were sold out at the presale, and none were available for the general public! Ticketmaster cancelled general sale tickets!

black text on a white background

source: theverge.com

It was all over the headlines and the issue even went all the way up to Congress! Below is a timeline summarizing the headlines of events that transpired. If you want to read more about it, here’s the link.

a close-up of a sign a black text on a white background a black text on a white background a black text on a white background a black text on a white background a close-up of a sign

source: people.com

Wow! Did I ever get lucky and have been fortunate to have had a credit card that not only gives me excellent benefits and earns me a minimum of 2X on all spending but also access to presale concert tickets? Had I not spent time and effort into getting US credit cards many years ago, I would have never gotten these tickets at face value.

Booking Flights to the Taylor Swift Concert

Finding flights between Ottawa to Chicago was easy as there is only one carrier that flies direct, which is United. I wanted to avoid Air Canada and others as I didn’t want to deal with connections. In 2023, I have zero faith in North American airlines, especially Air Canada and Westjet, who I’m sure would have caused an Irregular Operation (IRROP) for and lose my bag too.

Taylor Swift Concert

Embraer E75 aircraft running between Ottawa and Chicago, source: Business Insider

The direct United flight between Chicago and Ottawa, if booked through Aeroplan, would only cost 10,000 Aeroplan points. This is a great deal, but taxes are slightly high on the Ottawa-Chicago route versus Chicago-Ottawa: a screenshot of a computer

 a screenshot of a computerPricing sourced from aircanada.com

Regardless, this comparison was moot as no award space was available, so I had to purchase the tickets in cash. I opted to book the outbound and return separately and book them as refundable tickets. This is because if award seats become available through Aeroplan, I could then cancel and refund. What I like about United is that refundable fares generally cost very little extra on transborder routes. In the following example, it costs only $56 extra.

a screenshot of a flight schedule

Economy vs Economy refundable fare. Created from united.com

I purchased the tickets using my United Travel Bank dollars. I accumulated and continue to accumulate travel bank funds by taking advantage of one of the the airline benefit that many US American Express credit cards offer.

a close-up of a white background

a screenshot of a phone

Close to departure, I got an ExpertFlyer alert that award seats had opened on the Chicago-Ottawa flight, so I cancelled and refunded my United ticket and rebooked using Aeroplan. Note that you need to call United to get them to refund to Travel Bank as, by default, the system will issue a flight credit, which is not what you want. a close-up of a sign

In summary, here is how the flights priced out in the end, per person:

  • Ottawa-Chicago: $356
  • Chicago-Ottawa 10,000 Aeroplan Points + $75

Lastly, I’ll add that because I have United Silver status, which I acquired as a Marriott Titanium member, I confirmed seats on the cash-paid and Aeroplan tickets by calling United. Then, at T-24 hours, I got free Economy Plus seating for the entire family!

Concert Accommodations

Concert tickets bought. Check. Flights booked. Check. The only thing remaining to secure was accommodation. In hindsight, this should have been the first thing I checked before purchasing the tickets. This is because when I started looking for accommodations in the city, I was stunned to find that every hotel in the core of Chicago either sold out or priced very high; it seems that hotels inflated their prices for that specific concert weekend. Here’s a look at the prices for Hyatt, Hilton, and Marriott:

a map of a city with many locations

Marriott Hotel Availability, source: Marriott

a map of a city

Hyatt Hotel Availability, source: Hyatt

a map of a city

Hilton Hotels Availability, source: Hilton

By sheer luck, I discovered that the Courtyard by Marriott Chicago Downtown/Magnificent Mile had availability on points at 32k per night despite the cash rate being $557. Using points was a no-brainer in this case, and in fact, I was able to apply 3 Marriott 35k Free Night Awards for all three nights, which meant the hotel would be fully covered free of cost!  The hotel itself was fantastic. It was modern, clean, and situated in the heart of the Magnificent Mile.

a room with two beds and a desk

Courtyard by Marriott, Magnificent Mile, Chicago

Taylor Swift Concert

Courtyard by Marriott, Magnificent Mile, Chicago, source: Marriott

I’m glad to have kept multiple Marriott Bonvoy credit cards open to earn these yearly free night awards, as they always seem to provide a greater return than the annual fees paid for them. American Express Canada has a great promotion right now where you can earn elevated 75,000 welcome bonus points and a 35K free night award every year after that.

The Big Surprise & The Taylor Swift Concert

We did not inform Zoe about the tickets until a few hours before the concert. She had no idea why we were in Chicago. She assumed it was just one of our other trips like we always take.  When we surprised her, she was utterly speechless and excited like I’d never seen her!

a girl sitting on a couch looking at papers

a girl sitting on a couch holding a picture of herSo, how was the concert? Well, it was pretty mesmerizing in opposite ways for me and Zoe. While I was facing the utmost discomfort, surrounded by screaming and singing Swifties, I also got joy at the same time watching Zoe enjoy herself to the fullest! It indeed was a magical evening for her!

Taylor Swift Concert

A massive crowd of over 60,000 people at Soldier Field, Chicago

a girl with long hair wearing a white shirt with a picture on it


I am attaining the unattainable. This is what points and miles have given me. After years of flying first-class and staying in 5-star hotels, only my daughter’s happiness can make me smile. This is exactly what I accomplished by taking Zoe to a surprise Taylor Swift concert. I leveraged the full power and knowledge of points and miles I’ve acquired from others in my circle, including experts from our PMB Team: Anshul, Allan, Mohammed, and Dalia.

For my own sake, I hope I don’t have to endure another Taylor Swift concert, and I can ‘Shake It Off’ all the embarrassing emotions I felt during those gruelling 3 hours. But oh wait, Taylor Swift just announced international concert dates in 2024…..

Taylor Swift Concert


Ethan July 4, 2023 - 9:57 pm

Great article! Nice to read about using miles and points for a magical family experience! The first class flights will blend together over time but this is a memory that will last forever.

Sash July 5, 2023 - 2:17 am

Thanks Ethan for the feedback.
You hit it on the nail about first-class flights blending in together, especially if they are flown so often. But an experience like this concert will be a lasting memory for sure.

Anthony July 2, 2023 - 11:22 am

Great Article Sash !! This is also why I love poonts and miles… the ability to tick off bucket list “events” off your calendar and enjoying it with familiy or friends is even better.

I did Disney in Florida with my folks a while back for a Birthday. Flights were free and we stayed at great hotels like the Hilton Waldorf and Marriot Swan Reserve all on points for free too. That trip would have otherwise cost thousands of dollars.

Hopimg to do a few concert festivals soon and this article has great tips Sash ! How again can I credit my United Travel Bank with my US Amex Travel credit ?

Did you save a video of Zoe’s screams of joy when she saw her tickets ? THAT is what points and miles are all about ❤️

Sash July 5, 2023 - 2:12 am

Thanks for the feedback Anthony!
It really does feel great to take friends and family to experience experiences just like you did at Disney!
I wish I could post the video here for Zoe when we gave her the tickets. Rather than a scream, it was just silence for a bit as she was utterly speechless, then the excitement came after. It was fantastic! 🙂

Sarah July 1, 2023 - 12:39 pm

This is soooo cute! Glad it was an easy experience getting the tickets. A good reminder what this game is all about!

Sash July 1, 2023 - 11:00 pm

Thanks Sarah. Ya, I seem to have gotten really lucky with the tickets.

John the Wanderer July 1, 2023 - 9:32 am

Good job Dad! People around here went crazy for the show in Minneapolis last week. They were paying $2k+ for tickets. Its pretty cool you got them for face value!

Sash July 1, 2023 - 11:03 pm

Thank you!
I heard the same that tickets were going for about the same amount in Chicago too. It’s crazy yet people are paying for them!


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