A Midsummer Flight’s Dream: How I’m spending only $300 for my midsummer vacation’s flights

This summer, I’m making the same voyage I made last summer, except I’ve added one new stop.

My goal with this trip was to be as efficient with money as possible. My focus is to minimize my hotel and airfare expenses while maximizing the amount of time I spend outside of Seattle. I also planned stopovers and when I’d be in each city based upon the following factors:

• Hotel costs (because they varied based on the dates of my stay)
• Flight costs
• Being able to see the Macy’s 4th of July fireworks in NYC
• Staying out of Seattle as long as possible

While I don’t have anything too special to share about my hotel plans (except for the fact that I’m getting $140 back on my stay at a Courtyard), I’m super excited about my flight plans.

Bonus: I’m visiting all three New York City-area international airports in this trip!

Open jaw from Seattle to Chicago returning from New York (Alaska Airlines)

Remember that 737 MAX 9 incident in January where the door plug blew out midair? Although I was safe and sound in Texas when it happened in Oregon, I didn’t realize that it would soon have an impact on my plans. I was scheduled to fly to and from Orlando later that month. Both of those flights got canceled. I spent an insane amount of time trying to figure out how to reroute myself.

So in April, Alaska Airlines finally got around to making things right for me. They called me, stated how much they valued my business as an MVP Gold 75K member, and issued me a $450 flight voucher.

At first I was ecstatic. Then I found out there was a catch, as there always is: it had to be used all at once on Alaska Airlines-operated flights. If a booking cost less than $450, the remaining amount is forfeited.

So I had to wait for the perfect opportunity for a flight that I knew would cost more than $450, but no more than $550, because I don’t want to pay more than $100 out of pocket in this sort of situation.

Thankfully, I knew exactly when this would come in handy: transcontinental flights from Seattle to the East Coast. Traditionally, the round-trip tickets have cost me $500 or more, depending on when I’m traveling and how early I book.

When I was investigating my trip, I eventually decided to fly to Chicago first before continuing onto New York City. This necessitated an open jaw, because Alaska Airlines does not fly between Chicago and NYC.

In total, this open jaw cost me $77.46. That’s by far the least amount of money I’ve ever spent on flying to the East Coast.

One-way from Chicago to LaGuardia (American Airlines)

This is the segment I spent the most on out-of-pocket. The ticket was $119.47 cash. No discounts. Basic economy would have been $85, but I have a policy of never booking basic economy. It was cheap though, so I was happy enough about it.

I booked on American Airlines simply because I’m oneworld Emerald based on my Alaska MVP Gold 75K status.

One-way award ticket from Newark to Burlington, VT (United Airlines)

The last portion of my trip would involve me going to Montréal by flying to Burlington, VT and then renting a car to drive to Montréal. I explained my general idea in a previous post, but I changed up the way I’d book my flights.

As I scoured through different flight options, I found a super cheap redemption for a night flight from Newark to Burlington, VT on United Airlines. It was only 6,000 Air Canada Aeroplan points plus CA$46.70 (equivalent to US$34.24 when I paid). On United, it would have cost 15,000 United MileagePlus miles. Using Aeroplan rather than MileagePlus to book this flight was not only a no-brainer, it was also resourceful. I also took a flight on Air Canada last year and had a little over 5,000 points lying around in my account. Meanwhile, I only had 389 points in my MileagePlus account. I only had to transfer 1,000 points from Chase or Amex to finish making the booking. So easy.

I also paid $10.99 for a preferred seat in the front so I could leave the plane as quickly as possible to pick up my rental car at night, before Avis closes for the night at midnight.

The only risks I see with this plan is if the flight gets delayed more than expected (past when Avis closes) and/or if I have trouble with picking up the rental car. I’ll also need to drive for 1.5 hours in the dark from Burlington, VT to a suburb of Montréal, all while needing to cross the land border.

But for $45.23 in total, this is a cheap flight that I can’t really complain about. I’ll just grab some Tim Hortons on my way up to Montréal to keep me awake behind the wheel.

One-way from Burlington, VT (Delta Air Lines)

For returning to New York City, I booked a midday flight with cash on Delta from Burlington to JFK. Four hours after arriving at JFK, I’ll take my long transcontinental flight from JFK back to Seattle.

I found a one-way flight for $258.49 (refundable and with a preferred seat).

Normally, this would be too unreasonably expensive for a one-way flight, especially after I just found a 6,000 points redemption on Aeroplan for the way here. However, the way back was a 6am to Newark, which wouldn’t work for me when I had to drive all the way from Montréal to the Burlington airport.

Instead, this Delta flight was at a great time! It would give me plenty of time to connect to my flight from JFK to Seattle later that day.

Even better, I can use one of my annual Amex Platinum perks: the $200 flight incidentals credit. Now, you might be thinking, this is not an incidental! This is regular airfare.

Well, you see, there’s a neat trick where if you buy a Delta gift card for $50, you can then combine that with a card transaction that’s under $250. Amex will recognize that as an “additional collection” and will count your $200 credit towards it. It’s an open secret.

Does it really work? Well, I helped my friend use this exact method. He was able to find a $288 round-trip on Delta. He bought a $50 gift card and got all $200 reimbursed. That meant he only spent $88 for his flight.

So, if all goes well, I will also have the $200 applied to this flight, bringing this flight to only $58.49.

Total net spend

• Open-jaw: $77.46
• One-way from Chicago to LaGuardia: $119.47
• One-way from Newark to Burlington, VT: $45.23
• One-way from Burlington, VT to JFK: $58.49

Grand total of my net spend: $300.65

That means I have 5 flights booked for visiting three different cities, all for only for $300.65.

I’m super pumped to have such a frugal set of flights lined up and I can’t wait to enjoy exploring Chicago, New York, and Montréal.