Can ChatGPT Help Me Keep Airline Status? I Put It to the Test

ChatGPT has taken the world by storm, providing users with answers to just about any situation. Recently, I decided to see whether it could help me maintain elite status with both Alaska Airlines and United Airlines by generating travel ideas that fit around my work schedule.

My prompts were straightforward:

Find routes that would help me maintain status with both Alaska and United.
Build trips around federal holidays and weekends, as I work for a municipality.
Take me to places I’ve never been, including San Diego, Cabo San Lucas and Anchorage, Alaska.

ChatGPT responded with a customized calendar of suggested trips for 2026:

Updated 2026 Travel Calendar: Alaska MVP & United Premier Silver

Jan. 17–19 | United | ORD–DCA–ORD
MLK weekend, PQPs
Feb. 14–17 | American (credit to Alaska) | ORD–PHX–ORD
Presidents Day, Alaska miles
March 7–9 | United | ORD–DEN–ORD
Weekend segment run
April 4–6 | Alaska | ORD–SEA–ORD
Alaska segment required
May 23–25 | United | ORD–IAH–ORD
Memorial Day weekend
June 13–20 | British Airways (credit to Alaska) | ORD–LHR–ORD
International mileage run
July 3–6 | United | ORD–SFO–ORD
Independence Day trip
Aug. 15–17 | American (credit to Alaska) | ORD–SAN–ORD
First-time trip to San Diego
Sept. 4–7 | United | ORD–ANC–ORD
Labor Day in Anchorage
Oct. 10–12 | American (credit to Alaska) | ORD–DFW–ORD
Alaska-marketed flight
Nov. 25–29 | United | ORD–MIA–ORD
Thanksgiving holiday
Dec. 19–22 | American (credit to Alaska) | ORD–SJD–ORD
Weekend in Cabo San Lucas

At first glance, I checked the schedule to see if it followed my guidelines. For the most part, it did. However, I noticed some trips were scheduled from Saturday through Monday, which isn’t ideal. I typically prefer leaving Friday and returning Sunday. That’s on me—I could’ve been clearer in the prompt.

There were also a couple of questionable travel dates. For instance, the calendar had me flying to London the entire week of Juneteenth, and it scheduled a trip to Cabo just before Christmas from Saturday to Tuesday—odd timing for someone with limited PTO around the holidays.

Next, I evaluated whether these trips would actually help me retain elite status.

For Alaska, the MVP tier requires flying 20,000 miles. Based on calculations from Alaska’s website, just the February and April trips alone would earn me nearly 9,000 miles. If I continued with the full plan, I’d likely hit the 20,000-mile threshold.

One detail I found interesting: ChatGPT suggested I could book American Airlines flights and credit them to Alaska Mileage Plan. I’ve never purchased a flight through American’s website that was operated by Alaska, so that will be something new to try. That said, if I book all eligible flights directly through Alaska’s site, I should be fine.

For United, retaining Premier Silver requires 12 PQFs (Premier Qualifying Flights) and 5,000 PQPs (Premier Qualifying Points). According to the calendar, I’d only reach 12 PQFs, three short of the required 15. One tip I’ve learned: booking flights with layovers can boost your PQF count, as each segment counts separately.

PQPs are harder to track. United bases status mostly on dollars spent, so the rule of thumb is to spend around $5,000 to requalify. Without exact pricing, it’s difficult to tell how close the calendar gets me, but the structure provides a solid foundation.

Final Thoughts

While not perfect, ChatGPT provided a useful starting point. With a few tweaks to the travel dates and routing strategy—particularly for United—it’s possible to maintain elite status with both airlines. For travelers looking to maximize their loyalty programs while working within time constraints, AI might just be the assistant they didn’t know they needed.