$127 Find Cheap Flights from Puerto Rico to Madison

American Airlines is a miserable experience. It is predictably miserable, in the sense that every time I fly American, I brace myself for the certainty that it will be unpleasant and uncomfortable. But it is unpredictable in the sense that I never know if the flight will be on time or delayed nine hours (both happened to me this week). I never know if I will be able to sit in the seat that I selected when I purchased the ticket or if I will be told by Customer Service (!!!) that I must relocate from first class to a seat in the back of the aircraft with no explanation (both happened to me this week). Will the food be frozen and half defrosted, or scalding hot? Will the drinks be warm? Will the flight attendants be surly and mean? Will the toilets be cramped and foul? Will the seats be narrow and uncomfortable? Will there be a real electric outlet at the seat, or just an unreliable USB-2 port? Will there be enough seats in the boarding lounge or just a few? Will the boarding process be smooth and efficient, or will the gate agents mess it up and delay it needlessly for 30 or 40 minutes? Will the catering and cleaning crew be prompt or will they take an extra 30 minutes? Will the brakes on the aircraft work properly, or will the pilot delay takeoff for four hours while the ground crew attends to what can only be described as routine maintenance that should have been done the night before? I've eexperienced every one of these unpleasant things this year, 2026. The only thing I can reliably count on is that American will find a new way to make the experience of flying as miserable as they possibly can.

Flight was fine, but not having WiFi was a major negative

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Wifi was spotty. Tray table was very dirty when I sat down.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

The plane was very creaky and lots of ringing. Plane was dirty and dingy. I couldn't hear the captain's announcements from the flight deck. Not sure if it was the captain or the audio equipment, but good thing there wasn't an emergency where we needed clear instructions. The overhead compartments were clearly full, but the flight crew allowed people to stand in the back with their carry on luggage. Then after everyone boarded, they had to go to the front to gate check their luggage because there was no room for their bags and then they returned to their seats...such a waste of time when clearly the overhead compartments were full when they originally boarded.