San Francisco Trip Deal: $256 round-trip from SFO to Costa Rica on Copa Airlines

Copa Airlines has some pretty amazing flights from San Francisco to San José Costa Rica right now. Flights start at $256 round-trip, after taxes with open availability between October 2018 and May 2019.

Copa Airlines is part of the Star Alliance and these flights are coded “T,” which earn 100% Premier Qualifying Miles on United, so this can make for a great mileage run.

To find this deal, use my Expedia link to search for flights between SFO and SJO.

United is keeping its PQD credit card waiver for 2018… or is it?

To earn Premier elite status on United Airlines, you need to fly a certain amount of miles (called “PQM” or “premier qualifying miles”) or segments (“PQS” or “premier qualifying segments”) and to spend a certain amount of money on United flights (called “PQD” or “premier qualifying dollars”).


So, to obtain Premier Silver status, I would need to fly 25,000 PQM and spend $3,000 PQD. An issue with this system is that, especially with cheap flights, it can be difficult to reach the PQD. For example, in 2017 I earned 31,384 PQM on United but only $738 PQD.

United, like American and (new for 2018) Delta, had a workaround — you could spend $25,000 on a United-branded credit card and receive a waiver of the PQD requirement for Silver, Gold, and Premier status.

However, all mention of the waiver has been taken off the website, only mentioning it in reference to 2017.


Well, I’ve got some good news (kind of) — after spending nearly an hour on the phone with United (and speaking to 7 different representatives) , they confirmed that the credit card PQD waiver will still apply in 2018.

That said, every time I asked for it in writing — either on the website or in an e-mail to me — they refused. They agreed to make a note on my account saying they’d told me the waiver would apply, but there’s nothing stopping them from announcing they’ve discontinued the waiver at this point.

I don’t think United has motivation to discontinue the waiver and I appreciate their customer service saying it will continue in 2018, but as a lawyer, I want to see it in writing.

Portland Trip Deal: $271 round-trip from PDX to Quito, Ecuador on American Airlines

American Airlines is putting flights from Portland, Oregon to Quito, Ecuador on sale! Flights start at $271 round-trip, after taxes with availability in September and October 2017.

This is an incredible deal to South America and if you’re thinking of going, this deal won’t last long!

To find this deal, use or Google Flights and search for flights between PDX and UIO.

How I scored a lie-flat bed on American Airlines for $106.20

Did you know that American Airlines uses lie-flat bad in its first class between New York City (JFK) and Miami?

When I was looking at booking a flight between these cities, American Airlines has the best deal, coming in at $106.20 after taxes for June travel. When I went to pick a seat, I noticed that the plane had lie-flat beds (notably, the flight on American leaving later in the day did not), and decided that I would request a 500-mile upgrade for the flight.

For those who don’t know, American Airlines has a unique feature where, once you obtain premier status on the airline, you’re given around 500-mile upgrades to use for future flights (with Gold, I was given 10). For each 500 miles that you fly, you need to use 1 of your 500-miles upgrades. If you want to purchase more upgrades, it costs $40 for each one.

I generally like this system, as it makes it so you only request an upgrade when it’s most beneficial to you – and I’ve found I’m much more likely to get a 500-mile upgrade when I use it, compared to complimentary upgrades on United, where I also have status.

Unfortunately, the flying distance between JFK and MIA is 1,090, meaning it cost 3 500-mile upgrades (if it was just 90 miles less, it would have been 2!). Still, I decided to try for the upgrade because of the flat bed.

The flight was fairly empty, and I got confirmed for my upgrade at check-in. Because I’ve yet to go through all 10 500-mile upgrades (and I’ve upgraded on 3 flights now, including Turks & Caicos to Charlotte), I was able to score a flat bed for cheap!

The flight wasn’t particularly amazing, but, despite the short flight time, I actually used the bed and took a nap. Since I doubt I’ll maintain my American status, the good news is that the flight was around $300 to book directly for the flat bed; which, although not ideal, isn’t totally unreasonable.


How I scored 3 nights in an ocean-view room at The Ritz-Carlton in Miami for $337.30 total

I spent a lot of time going to Florida as a kid. As a Jew from New Jersey, many of my relatives made the “Jewish Migration” from the northeast to South Florida, and I would (generally) love my visits down there.

As I grew up, I became less in love with Florida, but always managed to have fun whenever I went. That’s why I knew I had to hop on this amazing deal I found at The Ritz-Carlton in Key Biscayne.

I was first alerted to the deal by an e-mail from I definitely recommend singing up for their newsletter – while most deals will likely be unavailable simply because of location, a few pop-up, like this one, which are incredible.

The original deal was $49/night (before fees) for an Ocean View, 1 Bedroom Residential Suite, so I booked the first dates I found available, which were in mid-June. After fees and taxes, this came $261.03 for 3 nights. I was in heaven. I even made sure to book on The Ritz-Carlton website directly, thinking there was a better chance they would honor this deal than a website like (which, in my experience, almost never honors these mistaken hotel fares).

But my dreams were short lived. A few days after I booked this deal, I got an e-mail from hotel itself, saying that they had to charge me full price for the room. Being a lawyer, I fought them on it. In fact, I had a back-and-forth with one worker for around a month, and finally got him to give me less nice, but still great deal – instead of what I originally booked, I was offered 3 nights (over the same dates) in an Onceanfront View Guestroom at a rate of $674.61 after taxes. The actual rate for room (according to the hotel’s website) is $1,974.11 for the same dates. So, although I am paying much more than I had anticipated and am losing a suite, I am still getting an incredible deal.

Even with my deal, I was still feeling too cheap to pay it. Miami can be fun, but Key Biscayne is a little slower and it’s in June, when weather down there is far from ideal. But not wanting to give up on my hard work of securing a great price, I reached out to an overworked friend of mine, easily convincing him of his need for a weekend away. He agreed to split the cost with me, making my total damage $337.30 for 3 nights on an ocean-view room in The Ritz-Carlton in Miami.

I’ll be sure to update you after my stay to let you know how it was!


San Francisco Trip Deal: $429 round-trip from SFO to Medellín, Colombia on Copa

Copa Airlines, a member of the Star Alliance, is putting flights from San Francisco, California to Medellín, Colombia on sale. Flights start at $429 after taxes, with dates found from August through October.

Medellín is an amazing location for working remotely (as well as one of the most beautiful cities I’ve ever visited).

To find this deal, use Google Flights and search for flights between SFO and MDE.

Los Angeles Trip Deal: $446 round-trip from LAX to Kuala Lumpur, Malaysia on United, ANA

United and ANA are putting flights from Los Angeles, California to Kuala Lumpur, Malaysia on sale, and the deal is amazing. Flights start at $451 after taxes, with dates found from August through November.

Malaysia is one of the countries I hope to visit in 2017, so I may have to hop on this deal.

To find this deal, use Google Flights and search for flights between LAX and KUL.