Instead of settling for economy, I pivoted my search and began looking for flights out of Chicago O’Hare, a nearby—and much larger—airport. Ultimately, I was able to find business class availability from Chicago to Madrid with a connection in Dublin on Aer Lingus, and I booked it through British Airways. Savvy travelers can do this because both airlines are partners and you can book travel on one by using the points—called Avios—you have with the other.
Because my date was off-peak, I snagged a ticket for 62,500 Avios instead of the usual 75,000. To book, I transferred the points over to British Airways from my American Express Platinum Card. (Amex also transfers to Aer Lingus itself, but there was no difference in what the two airlines were offering in price, and my Amex and BA accounts were already previously linked.)
At that point, all that was left to do was find a quick flight that would get me from Minneapolis to Chicago with enough time to make the flight to Madrid. Because economy-class tickets were cheap at $118.10, I chose to pay cash and save my United MileagePlus miles for the return leg of my journey. While I normally would have used my Amex Platinum to earn five points per dollar, this time, I used my United Quest Card. It earns three points per dollar on United flights, and at the time, I was working toward a promotion for extra Premier Qualifying Points, which help you earn elite status with United.
How I booked lodging in Madrid for The Eras Tour
When choosing hotels, I normally try to look for design-forward options, but with only one night in Madrid, I knew it would be best spent by staying as close to the concert venue as possible. Luckily, I spotted a Hilton property: the Canopy by Hilton Madrid Castellana, just a 10-minute walk from the stadium. The prospect of not having to battle through tens of thousands of people to find an Uber was too good to pass up.
In cash, the price for a room at the Canopy would have been around $500, which is well above rates for the property I saw on other dates. But shockingly, the price in points did not seem to be marked up much for the concert. I got a room for 60,000 Hilton Honors points earned with my Hilton Honors Aspire from American Express, and it couldn’t have worked out better. The location was perfect, and the hotel had special themed events and decor for visiting Swifties.
How I booked flights and lodging in Mallorca
Like flights on Aer Lingus, flights on Iberia—Spain’s flag carrier—can be booked through British Airways, so when I was searching for a way from Madrid to Mallorca to squeeze in some beach time for the day after the concert, the airline was the first place I turned to for travel.
