San Diego Trip Report: Buyups, Bargains & Beaches Preview

A cheap Alaska fare, an upgrade worth taking a shot on, three nights at a Tribute Portfolio hotel earning AA miles, a downtown taco tour, and a return routing through Chicago where American and United are going head to head. Here's how this one came together.

Some trips get built around a destination. This one got built around a cheap fare during one of the busiest domestic travel periods.

I noticed Alaska was running a sale to San Diego out of Dulles — $130 direct. It was time to visit the West Coast again and everything else fell into place — including a return routing through Chicago that takes advantage of what's shaping up to be one of the more interesting competitive situations in domestic aviation right now. More on that later.

Here's the full plan.

Getting to Dulles: Silver Line

DCA is the easy airport for short hops, but it's slot restrictions mean most long-haul and international flying runs through IAD, and the Metro's Silver Line has made getting there considerably less painful than it used to be.

For anyone not familiar: the Silver Line extended to Dulles a couple of years ago and effectively ended the argument for a rideshare or taxi on any trip where you're not checking a lot of luggage. It's cheaper and beats the traffic. When I'm on the Metro to Dulles, I know it's the start of a fun adventure.

The Lounge at IAD: Sapphire by Etihad

After arriving at the aiport I plan to check out the Sapphire Lounge by Etihad, accessible to Chase Sapphire Reserve Cardholders. The space is also accessible to general Priority Pass holders via once annual access. Dulles's lounge situation has improved a lot in recent years and this one is among it's best.

Chase's LGA Lounge

The Outbound: Alaska IAD–SAN

The headline of this trip is a $130 direct fare from Dulles to San Diego. For a transcontinental nonstop it's a great fare, especially if your status grants complimentary Premium Class extra legroom seats.

This flight was also available at 12,500 American AAdvantage points. Running it through the MilesMate American Airlines Points vs Cash calculator, cash came out ahead — the points redemption works out to around 1.0¢ per point, which sits below the 1.4¢ baseline I use for AA. But the bigger reason to pay cash here is the upgrade. Booking with AA points takes Alaska upgrade eligibility off the table, and on this particular flight that's worth preserving. The upgrade situation looks promising.

As of writing, eight of twelve first class seats are still open with 60+ in economy. Saturday evenings on transcontinental routes are about as favorable a setup for upgrades as you're going to find — leisure-heavy with less competition from those with elite status. As long as buy-up pricing doesn't get too aggressive, there's a real shot at clearing. It's been about a year since I last flew with Alaska, so I'm excited to see if I can score an upgrade via my AAdvantage status.

I'll cover the full upgrade strategy in a separate post, but the short version is that flight timing, day of week, and cabin availability at the time of booking all matter more than you might realize when it comes to improving your upgrade chances.

The Hotel: Alma San Diego Downtown

After arriving, I'll spend a few nights at the Alma San Diego Downtown, a Marriott Tribute Portfolio property in the Gaslamp Quarter. These were booked through AA Hotels at $170 a night cash. The reason to book through AA Hotels rather than directly: in this case my stay earns 7,100 AAdvantage miles and Loyalty Points. That more than covers the AAdvantage award ticket for my final trip leg from Chicago. Effectively the hotel is paying for the flight home.

The Tribute Portfolio sits in an interesting position in the Marriott lineup — these are independent hotels with their own character that still earn and redeem on Bonvoy, without the regularness of a standard branded property. While I typically opt for Hyatt or IHG properties, I decided to take a chance on this well priced property. It is a newer addition to the Tribute collection and the Gaslamp Quarter makes it centrally located in downtown.

In San Diego: Tacos and Route 992

San Diego has a strong claim to being one of the best food cities on the West Coast, and the taco situation deserves special attention. A downtown taco crawl is on the agenda — spots and a full writeup coming soon.

After a few days of exploring, I'll head to the airport via Route 992, an MTS bus that runs directly between SAN and downtown. San Diego airport sits unusually close to the city center and the 992 is a quick, cheap connection that most people skip in favor of a rideshare. It stops right outside the terminals and offers contactless payment options. For a solo traveler with a carry-on it's a no-brainer.

Finally there's also a Priority Pass lounge at SAN — another Sapphire Lounge — which we'll check out before departing California.

The Return: Through Chicago

The routing home is where things get even more interesting.

American and United are competing hard out of O'Hare right now. Both carriers have been adding capacity, pricing aggressively, and going after each other's flyers. What this means is that there are plenty of beneficial opportunities for travelers to, from, or through Chicago.

Routing through ORD on the way back to DC made a lot of sense once I started looking at what was available.

Alaska SAN–ORD: Available at $280 cash or 25,000 points. Running the points vs cash math, the paid ticket was the easy call. Economy was only around $70 cheaper than first class on this flight, which for a 4 hour flight, made it an easy buy up decision. Pricing quirks like this can appear when the economy is selling - but premium seats aren't.

American ORD–DCA: I then connect home on a 6,000 mile AAdvantage award ticket. Carefully monitoring the American app after booking allowed me to snag a $40 first class buy-up. The flight is operated by an A319, which only has 8 seats up front (and is rarely a realistic upgrade.) An affordable buy up was the right move rather than gambling on a 30+ person upgrade list.

This is the last departure of the day, which has its own implications. This specific flight also has some history for me that I'll save for the review.

Oftentimes this route is the E-175 which offers much better upgrade chances because of its ratio of economy to first seats.

The Full Series

Post	Status
Silver Line to Dulles	Coming soon
Sapphire Lounge IAD review	Coming soon
Alaska IAD–SAN + upgrade result	Coming soon
How to improve your Alaska upgrade chances	Coming soon
Alma San Diego Downtown review	Coming soon
San Diego downtown taco tour	Coming soon
SAN Route 992 bus review	Coming soon
Sapphire Lounge SAN review	Coming soon
Alaska SAN–ORD review	Coming soon
AA ORD–DCA A319 First Class review	Coming soon

Related: Alaska Atmos Points vs Cash: How to Decide · AA DCA–FLL A319 Main Cabin Extra Review