Flights for 2025 Independence Day Trip to Alaska

I made a trip over Independence Day to Alaska. This post would be about the flights back and forth, which were filled with lots of drama but everything turned out fine in the end.

Chugach Mountains

Ticketing

I first discovered this set of tickets in October 2024, when American Airlines offered a flight from Boston to Anchorage for just $260 on Saturday, June 28, with a connection in Dallas. The fare required a morning flight from Boston to Dallas, followed by the second of the two daily flights from Dallas to Anchorage, resulting in a layover of more than eight hours in Dallas, a prospect that didn’t trouble me at the time, as I thought I could use the opportunity to explore downtown Dallas. The timing seemed ideal, as June 28 fell on the Saturday before the July 4 holiday.
To complement the outbound journey, I found that Alaska Airlines had standard award availability for a return flight on Saturday, July 5, a redeye from Anchorage to Minneapolis. From there, American Airlines could bring me home to Boston, initially with a connection in LaGuardia (though later, due to schedule changes, the connection shifted to Chicago). Remarkably, the entire return trip cost just 15k American Airlines miles, which felt like an incredible bargain given the proximity to the holiday.
Even better, a month later, American Airlines reduced the BOS-DFW-ANC fare to $234, still in the main cabin. Needless to say, I didn’t hesitate to take advantage of this further savings.
I had previously visited Anchorage in both 2020 and 2021, and with soaring mountains lining the city’s skyline, I felt confident that another week spent there would offer abundant opportunities for rewarding outdoor adventures.

American Airlines Flights 2555 and 399 from Boston to Anchorage via Dallas Fort Worth

My flight to Dallas was scheduled to depart Boston at 6:52am, and I calculated that I could catch it by taking the first MBTA Blue Line train of the day, thus sparing myself the expense of a rideshare. The timing turned out to be a bit tight, but ultimately manageable.
American Airlines operated two daily flights from Dallas to Anchorage, flight 399 departing at 3:14 pm, and flight 395 departing at 7 pm. Unfortunately, first class on both flights was entirely sold out, so the prospect of an upgrade was out of the question. In the days leading up to departure, the earlier flight, 399, was also completely booked. However, I observed 7 available seats had opened on the morning of departure. Given that my ticketed flight 395 would arrive in Anchorage quite late, I decided to attempt standby for the earlier flight to try shortening what would otherwise be a very long day.
I understood that, when standing by for an earlier domestic flight in the US with checked baggage, it is common practice to have bags tagged on the standby flight. I had read that certain carriers (Delta) have special procedures to ensure that checked bags travel with the passenger. However, the checkin agent informed me that that’s not the case with American, and my bags would fly with the earlier flight 395, whether I made the standby or not. (That wasn’t an issue for me, since I was first on the standby list, and in case I didn’t make it, I would happily retrieve them from the baggage office instead of waiting for them at the carousel.)

After sorting out my checked bags, I entered the line for security screening at 6:04am, and cleared it 10 minutes later. Then I made way for the gate where boarding was underway, no time wasted.

American Airlines 2555
Boston, MA (BOS) – Dallas Fort Worth, TX (DFW)
Airbus A321 (N165NN)
Seat 3F
Scheduled Departure – 6:52am
Actual Departure – 6:56am
Scheduled Arrival – 10:09am
Actual Arrival – 9:14am
3 hours and 20 minutes
Here’s GPS tracking:

Here’s a video of the takeoff:

Breakfast
The omelet tasted quite good.

The flight to Dallas was largely uneventful. Low clouds hung over Boston, and much of the journey across the eastern states was shrouded in overcast skies, leaving little to see below. I spent most of the flight asleep, making up for the early start. With less headwind, we landed well ahead of schedule (and had a 14-minute wait for the gate to be available).

One minor discomfort arose during our descent: the cabin seemed somewhat over-pressurized. At an altitude of 2000 meters, the cabin pressure was 7 mBar higher than it was after landing, a subtle but noticeable difference for my sensitive drum.

Here’s a video of the landing:

For the next leg to Anchorage, it turned out that flight 399 had 12 available seats prior to departure, so all 8 standbys were cleared. First class was sold out, and unfortunately by the time my upgrade was cleared, all the main cabin extra seats were taken so I was relegated to a standard seat.

After boarding, we had an extended wait at the gate for “maintenance signoff”, which struck me as odd considering the aircraft had been on the ground in Dallas for quite some time before our scheduled departure. One would expect American Airlines to manage such matters in a more orderly fashion.

American Airlines 399
Dallas Fort Worth, TX (DFW) – Anchorage, AK (ANC)
Airbus A321neo (N446AN)
Seat 15A
Scheduled Departure – 3:15pm
Actual Departure – 3:55pm
Scheduled Arrival – 7:00pm
Actual Arrival – 7:04pm
6 hours and 9 minutes
Here’s GPS tracking:

Here’s a video of the takeoff:

Probably given the flight’s considerable duration, the crew procrastinated until 9000m elevation (23 minutes after takeoff) to turn off the seat belt sign, after which they started to peddle dinner. My status with American afforded me a free selection, which I picked the cheese plate. It proved merely edible, nothing more.

This was a very long flight, which I spent between naps and movie clips, with tedium gradually settling in as the hours wore on. However, things took a turn as we approached Anchorage, where the clouds broke up over Prince William Sound, revealing stunning sights of snowy mountains and glaciers below. Later, having descended beneath the overcast layer between 3500 and 4500m, the magnificent Chugach Mountains emerged into view—the very ranges I had planned to explore in the coming week.

Click here to display photos of the slideshow

Snowy Mountains

Chugach Mountains
I hiked Flattop-Flaketop loop the next day.

Overlooking Anchorage Airport

Distant Tordrillo Mountains

Chugach Mountains

Chugach Mountains
Last time I was in Anchorage, I climbed South Pioneer Peak. This time, I planned on East Twin Peak.

Anchorage against Backdrop of Chugach Mountains

We reached the gate at 7:10pm, and I retrieved my checked bags at 7:44pm. This 34-minute gap was beyond the standards some other carriers adhered to, but given American’s limited presence in Anchorage (and the general sense of sloppiness that characterized this flight), that’s hardly surprising.
On the flip side, this wait didn’t bother me that much in the end, as I booked my rental car based on my original flight’s arrival time, so I still needed to wait a little bit at the rental counter before the car’s ready.

Alaska Airlines Flight 59, American Airlines Flights 2619 and 1933 from Anchorage to Boston, via Minneapolis and Charlotte

Fast forward to July 5. I wrapped up the day’s activities much earlier than expected, and made it to the airport 4 hours before my flight to Minneapolis. As this was the weekend after the July 4 holiday, it was a bustling scene at the airport with numerous redeyes poised to depart for the Continental United States. This holiday exodus manifested in the long security screening queue, yet remarkably, Anchorage Airport offered a priority lane clearly marked for airline elite members, through which I effortlessly glided.

Click here to display photos of the slideshow

Passage
Between Rental Car Center and terminal.

Terminal Interior
Very long lines outside Sun Country checkin counter.

Delta Airlines B763 (N174DZ)
Delta operated one daily widebody between Anchorage and Atlanta.

In the days preceding my departure, the number of available first class seats on this Minneapolis flight fluctuated between 0 and 1. Since Alaska Airlines prioritized upgrades for its MVP 100k and 75k elites before any elites with American Airlines, I was #4 on the upgrade list hence wasn’t expecting an upgrade. Surprisingly, moments before departure, I checked my app and it showed I was upgraded, apparently claiming the final available first class seat. 😃

Alaska Airlines 59
Anchorage, AK (ANC) – Minneapolis St Paul, MN (MSP)
Boeing 737-900 (N238AK)
Seat 2A
Scheduled Departure – 10:35pm
Actual Departure – 10:35pm
Scheduled Arrival – 7:00am+1
Actual Arrival – 6:43m+1
5 hours and 8 minutes
Here’s GPS tracking:

As for the flight, I liked the retro style first class seats on Alaska Airlines with their generous padding, though I could envision the lack of head support if I was a few inches taller. I sat on the left side of the plane. Given the route and the season, my position promised a rare spectacle of both sunset and sunrise during this 5-hours flight. Only that this was a redeye where most people sought whatever slumber they could find, hence the crew explicitly suggested window shades to be closed to preserve the darkness of the cabin.

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Turnagain Arm

Sunset Glow

Twilight

Islands among Mississippi River

Here’s a video of the landing:

It was a somewhat bumpy ride from Anchorage to Minneapolis. After that, my original itinerary was

• Minneapolis 10:18am -> Chicago O’Hare 12:29pm
• Chicago O’Hare 1:20pm -> Boston 4:39pm

This schedule offered me a long connection in Minneapolis (over 3 hours) and a tight one in Chicago (less than an hour). Initially, this arrangement seemed ideal. I could enjoy the Escape Lounge (part of PPS) in Minneapolis. While the lounge proved spacious with passable breakfast offerings, many seats would have benefited from more thorough cleaning.

Sunday, July 6 promised an enticing morning of sports, Wimbledon and the Formula 1 British Grand Prix, that suited my interest. Just as I thought I could watch (most of) the Grand Prix before my Chicago flight, American Airlines notified me of a delay. The inbound aircraft (N309JR) was held up in Chicago, quite surprising as I had occasionally observed its punctuality for weeks prior. After a quick search, I discovered an alternative route:

• Minneapolis 9:52am -> Charlotte 1:30pm
• Charlotte 3:10pm -> Boston 5:21pm

This option would prove more efficient if I missed my Chicago connection (though it would arrive 42 minutes later if I made that connection). Anticipating further delays on the Chicago route, I called American Airlines to secure this “better” itinerary.

Curiously, I hadn’t appeared on the upgrade lists for either of my original Chicago-routed flights. I suspected that once Alaska Airlines confirmed my ANC-MSP upgrade, they “took over” control of the ticket, and some technical glitch removed me from subsequent upgrade lists. In Anchorage, Alaska gate agents had actually paged me regarding something like “reassociate vcr,” though they couldn’t identify the precise issue. With this in mind, it made sense to “reset” my ticket.

It turned out that the weather was very bad in Chicago with widespread delays that day. Had I continued onto Chicago with my original itinerary, I would get home 3 hours (instead of 42 minutes) late.

This screenshot, captured after boarding my Charlotte flight, shows my original flight’s inbound aircraft still queued for takeoff at Chicago O’Hare—already 20 minutes past its scheduled departure time.

American Airlines 2619
Minneapolis St Paul, MN (MSP) – Charlotte, NC (CLT)
Airbus A321 (N198UW)
Seat 1A
Scheduled Departure – 9:52am
Actual Departure – 9:58am
Scheduled Arrival – 1:30pm
Actual Arrival – 1:06pm
2 hours and 8 minutes
Here’s GPS tracking:

Here’s a video of the takeoff:

By the time I switched to the Charlotte flight, a single first class seat remained, with a lengthy upgrade list already in place. Fortunately, my status positioned me at the top of this list, securing me the coveted final seat. It’s quite the contrary for my connecting flight from Charlotte to Boston, with one person on the upgrade list and two first class seats available. Within half an hour, however, another traveler had joined the queue, relegating me to third position and ultimately leaving me in the main cabin. (I found myself rather surprised by the absence of lower-tier American Airlines elite members on that particular flight.)

As for the flight itself, MSP-CLT was just over American Airlines’ first class meal threshold (900mi) while BOS-ORD was under. Having properly stuffed my stomach in Minneapolis’ lounge (given there was no PPS lounge in Chicago O’Hare), the lunch felt a little bit too much. Apart from that, the flight was uneventful.

Click here to display photos of the slideshow

Lunch
My second time trying out this Chicken Breast.

Dirty Seat Belt
I expected better maintenance from American Airlines.

The flight from Minneapolis to Charlotte overflew Chicago, where I saw dense clouds below, indicative of ominous weather. The clouds gradually dispersed after that, revealing patchworks of landscape below.

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Ohio River
Near Cincinnati

Carowinds Amusement Park
Built across the state line of North and South Carolinas.

Here’s a video of the landing:

After landing in Charlotte, I attempted to visit The Club, a PPS lounge. Expectedly there was a waiting list. But after I gained entry, the experience proved underwhelming: its buffet part was almost non-existent, and the food that I ordered never came.

American Airlines 1933
Charlotte, NC (CLT) – Boston, MA (BOS)
Boeing 737-800 (N968AN)
Seat 8D
Scheduled Departure – 3:10pm
Actual Departure – 3:21pm
Scheduled Arrival – 5:21pm
Actual Arrival – 5:02pm
1 hour and 41 minutes

For the final flight back home, it was operated by a 24-year old 738 (N968AN). I noticed the floor yielded slightly whenever passengers walked down the aisle past my seat, which was somewhat disconcerting. Fortunately, the floor remained intact at the end of the day.
Curiously, the drink service for this flight commenced approximately an hour after takeoff, well beyond the halfway point of the flight, the cause of which remained a mystery.

It had been a long day so I was feeling a bit tired and slept through most of the flight, which went smoothly.
I checked two bags at Anchorage, which, following my itinerary change in Minneapolis, were both rerouted onto this flight (despite American Airlines app showing one of them had been stranded in Minneapolis. In a curious aftermath, American Airlines sent me an apologetic email regarding the supposedly delayed baggage and offered to deliver it to my address, presenting an opportunity for dishonesty had I chosen to falsely claim that I never retrieved the “left-behind” bag).
After collecting my bags 15 minutes after our gate arrival, I boarded the subway home, concluding the trip.
END

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