Let's Take a Day Trip

CHICAGO —It’s that time of year again across the frequent-flier corners of Reddit — travelers scrambling to close out their airline “status rings” before the calendar flips. I’m no different.

Right now, I’m sitting at 31,142 Alaska Airlines miles. I need 40,000 to lock in Gold status. Under Alaska’s current rules, status is earned by the number of miles flown, not how much you paid for the ticket — a policy that will shift in 2026 for the 2027 qualifying year.

With a few Alaska credits in my account, I pieced together a mileage run that starts with a flight from Chicago to Boston on American Airlines. Since American is part of the Oneworld Alliance, I should earn Alaska miles on that segment, too. From Boston, I’ll connect to San Diego and then continue on to Seattle — all today. Tomorrow, I turn around and fly back to Chicago via San Diego.

If all goes according to plan, the trip should net about 6,400 miles. I do have another run to Las Vegas scheduled next week, but this one is the big push: a same-day, cross-country hop through three time zones — breakfast in Chicago, lunch in Boston, a quick dinner in San Diego, and, if everything stays on schedule, falling asleep in Seattle.

Please note all times are central

10:45 a.m. — Chicago O’Hare

The drive from home to O’Hare was surprisingly smooth this morning. Traffic along the Tri-State Tollway — I-294 for the locals — moved without any issues. The only hiccup came when I tried to park at Lot F, the Multi-Modal Facility. It was full, so I had to switch to terminal parking, which costs more. Usually, when this happens, O’Hare hands out vouchers to cover the price difference. Not today. I’ll be emailing them later.

The bright side: I ended up parking right next to Terminal 3, and the garage is covered — a win with snow in Sunday’s forecast.

Inside the terminal, security was a breeze. There was no line at the priority lane, which is one of the perks of having Alaska status and, by extension, Oneworld benefits with American Airlines. At O’Hare — and at many airports — status holders get access to a dedicated lane that includes TSA PreCheck. If you travel often, I can’t recommend earning status enough.

My flight to Boston is scheduled for a 12 p.m. departure and is currently on time.

Next stop: Boston.

3 p.m. — Boston Logan

The flight from Chicago was uneventful, but not exactly enjoyable. There was no Wi-Fi on board — hard to believe in 2025 — so instead of working or streaming, I ended up chatting with the woman seated next to me. She’s originally from India but now lives in Des Moines and was headed to Boston on a work trip. A nice conversation, but still, no Wi-Fi.

We landed in Boston, and Logan looked far more modern than I remembered. It’s been years since I’ve flown through here, so the update was a pleasant surprise. I made a quick stop at Potbelly, grabbed a sandwich, a sugar cookie and a bottle of water, and just as I sat down to take a bite, my flight to San Diego began boarding.

At the gate, the agent gave me a puzzled look when I asked for a boarding pass. “How did you get through security without one?” she asked. I explained I had just arrived from Chicago on a connecting flight. Once that was cleared up, I asked the more important question: whether anyone was seated beside me in the exit row. Thankfully, no — the middle seat is empty, though there is a passenger in the window seat. For a six-hour transcontinental flight, this is pretty much ideal.

I bought Wi-Fi as soon as we took off, and so far it’s working well. Now it’s time to settle in, stretch out, and catch up on “Law & Order: SVU” as we make our way toward San Diego.

10:20 p.m. — San Diego International Airport

Even with all the extra space on the last flight, the fatigue is starting to set in. We landed in San Diego with barely any time to spare — the kind of tight connection where your next flight is already boarding as you’re walking off the plane.

For a moment, I considered calling it a night and catching a morning flight instead. But I pushed through. I ducked into the restroom, splashed some water on my face, and made the seven-minute walk to my next gate.

The good news: on the Seattle-bound flight, I’ll have the entire exit row to myself. That alone lifted my spirits. At this point, I’m only about three hours away from a hotel bed — and that thought is carrying me the rest of the way.

1:50 a.m. — Seattle-Tacoma International Airport

I drifted in and out of sleep on the Seattle flight, my head resting against the window but never fully comfortable. A headache and hours of travel will do that. But the flight was quiet and smooth — exactly what I needed at that stage.

Once I signed onto Wi-Fi, I started rethinking Sunday’s return trip. My original plan was to route back through San Diego to squeeze out more miles. But then I remembered a key detail about Alaska Airlines mileage earning: If you book a First Class ticket through Alaska’s website, even on an American Airlines–operated flight, Alaska awards 150% of the actual miles flown.
On status runs, that multiplier can be the difference between coming close and clearing the threshold comfortably.

So I canceled my original flight, received the credit instantly, and rebooked a First Class itinerary home for Sunday. After that, I put everything away and tried to get a bit of rest.

When we landed, the deplaning was quick. A “Welcome to Seattle” sign greeted me at the terminal entrance, and I don’t think I’ve ever been so happy to see one.

As of Sunday morning, I am 4,720 miles away from earning Alaska Airlines Gold status.