My recent review trip to Europe didn’t exactly go as planned, as I had a downgrade issue on the outbound, a frequent flyer account suspension on the Middle East detour, and now I want to share what happened on the return. After a great flight in American’s new “premium” Boeing 787 business class, I misconnected, and had to spend the night in Chicago.
There’s a reason I waited to write about this, which will become more apparent in a follow-up post…
In this post:
My American misconnect experience in Chicago
After a night at the Park Hyatt London River Thames, my return journey had me flying from London to Chicago to Miami, with a planned 1hr59min layover in Chicago (arriving at 5:00PM, and departing at 6:59PM).
The night before my flight, while in London, I could already tell that my flight would be delayed. A couple of American’s new 787-9Ps have some serious maintenance issues, despite being brand new. For example, my flight was on the new Dreamliner with the registration code N842AA, and look how badly that plane performed in mid-July…

I was flying on July 28 from London to Chicago on AA91, and the issues prior to that were clear. On July 27, the plane was nearly five hours delayed (due to a maintenance issue) flying from Chicago to Los Angeles. It was then supposed to fly from Los Angeles to Chicago to London, to position for my flight.

As you’d expect, there’s only so much time that can be made up. So the night before, American already delayed my flight, moving it from a 2:25PM departure to a 3:30PM departure. The flight was then scheduled to land in Chicago at 6:05PM, which is tight, but manageable, given that I have Global Entry, TSA PreCheck, and wasn’t checking bags.

The anticipated 3:30PM departure more or less ended up being correct, and indeed, that’s exactly when boarding wrapped up, and also roughly when the door closed. There was then a slight air traffic control delay on the ground (since we had missed our initial slot, due to the delay), but we actually made good time, and landed in Chicago at 5:48PM, 79 minutes before my connection was supposed to depart — easy peasy!
However, then there was no gate available for us (presumably because we were delayed, and Terminal 5 at O’Hare is super busy in the evenings), and that required nearly an extra 30 minutes of waiting.
While our flight showed an arrival time of 6:21PM, the aircraft started deplaning at 6:25PM.

We arrived at gate M27W, located toward the end of Terminal 5, and I was departing from gate H16, located at the very end of Terminal 3. Could I clear customs and immigration, take the train, clear security, and get to my gate, in that amount of time? I figured it would all come down to how early they closed the door on my connecting flight.
I went as fast as I could, and made good time, given the reality of both of my gates being toward the far end of the terminals, plus Terminal 5 and Terminal 3 being completely disconnected.
I arrived at my connecting gate at 6:53PM, six minutes ahead of the official departure time. Obviously that’s less than the 10 minutes prior to departure that doors usually close, though I also know American has been promoting how it’s holding more flights for late connecting passengers, and I figured maybe this is a case where they’d do that — after all, American has no connecting flights that depart from Miami after this flight arrived.
But nope, I arrived at the gate to find the “Flight closed” monitor.

Not only that, but the jet bridge had already been pulled back, so it seems like it wasn’t even close.

What’s funny is that after the fact, the flight status page showed a 6:58PM departure, five minutes after I arrived at the gate. In fairness, the departure time is generally calculated based on when the plane pushes back. The aircraft ended up arriving in Miami nearly 30 minutes early.

I was then rebooked on a flight at 5AM the following morning. American offered me three terrible hotel options, so I ended up just booking my own hotel for the night…
At least I’ll make $700(ish) from this ordeal?!
I was bummed not to get home the same night and be with my family. On the plus side, at least if you’re going to have something like this happen, it’s nice for it to happen on a flight departing the European Union or United Kingdom. The European Union has EC261, while the United Kingdom has UK261, which is essentially the same (but of course post-Brexit, the UK needs its own policies).
If you depart the UK on a journey of over 3,500 kilometers and arrive at your destination three or more hours late, you’re entitled to £520 (~$691) in compensation. To clarify a couple of points:
- This is based on when you reach your final destination, and not how long the delay on a specific flight is (this can work for or against airlines, depending on the situation)
- The only exclusion is “force majeure,” but in this case, the delay was caused by a late arriving aircraft due to maintenance issues
Hey, at least this puts a more concrete cost to American closing the door early and choosing not to wait for any connecting passengers, which is fair enough. We’ll see how easily American agrees to its obligations here, given that airlines love to blame everything on ATC or weather, even if it’s patently untrue. But I know what the regulations are, so…
Bottom line
Unfortunately my flight from London to Miami via Chicago didn’t quite go as planned, due to issues that American seems to be having with some of its new Dreamliners. The plane I was on has quite a bad maintenance record, and that ultimately caused my flight to be delayed due to a late inbound aircraft.
I missed my flight back to Miami, so American’s new program for holding more flights didn’t work in my favor, despite it being the last flight of the night. Fair enough, since I wouldn’t expect every flight to be held.
On the plus side, at least this itinerary qualifies for UK261 compensation, which makes me feel a bit better about getting home late. How much of a fight that becomes remains to be seen…
Europe is so much more advanced than America! You were lucky that you originated from a modern democracy and that you therefore had rights as a passenger.
Just curious how you got from Munich to LHR as I did not see any post regarding this flight?
@ P. Roberts -- I flew British Airways on an A320neo. I'll have a full review of the flight in my trip report series, but figured it wasn't worth a preview post. :-)
"On the plus side, at least if you’re going to have something like this happen, it’s nice for it to happen on a flight departing the European Union or United Kingdom. The European Union has EC261, while the United Kingdom has UK261"
I personally never connect from Europe into another US city but always fly non stop from Europe to my final US destination. And it is not because of the EU compensation but because...
"On the plus side, at least if you’re going to have something like this happen, it’s nice for it to happen on a flight departing the European Union or United Kingdom. The European Union has EC261, while the United Kingdom has UK261"
I personally never connect from Europe into another US city but always fly non stop from Europe to my final US destination. And it is not because of the EU compensation but because I rather stay another night in Europe than stuck at a US city. At least I can enjoy an extra night in London, Rome, Paris, Amsterdam but what good it makes it if I am stuck in Chicago, Detroit, NYC, so close but not at home yet. Same goes to fly out from the US to Europe. I rather fly from my home hub to any EU city than to another US city. If something goes bad with my flight, I at least just drive back home and sleep in my bed. If I make to Europe, there are tons of options to reach my final EU destination which includes trains if planes are delayed.
Did you know there are hundreds of airports in the US that don't have nonstop flights to Europe?
Yes, I did. But I am talking about my own experience and I am fortunate to live in a place that there are non stop flights to Europe. My comments were on Ben's decision to fly back home connecting at a US airport vs flying non stop to Miami. Having the option, I would never do that.
How did your father's trip back go?
@ mkleiderman — He stayed longer, and is in Lufthansa first class heading across the Atlantic as I type this. :-)
Last year I received £520 from AA for LHR-LAX arriving 4 hr 4 min late (what a difference a few minutes make!). AA certainly doesn't make it an easy online process. I had to write to customer service requesting the form, received back a canned apology, replied to that and someone sent me a form. About 3 weeks after sending the form I received a check for $652.
United pulled back the jetway but reconnected it for me in Houston!!!!! And I have no status with them
So many questions.......
Yes, it's only a success once you actually get it. Still fighting Iberia on it, they keep saying that what my delay was was out of their control. That's complete BS when the last few flights for that same route has always been delayed by more than an hour or so. I wish you luck on it as I am still in arguments with it with Iberia.
They made me miss my connection in Madrid to Milan FYI.
Can they blame the gate not being available?
Also strange foreign law would apply to a domestic connection. If the TATL is on time, and a domestic flight is cancelled, the UK can make AA pay up?
Yes. The whole itinerary is covered regardless if it's a domestic flight or not.
@ Sel, D. — Gate is considered within the carrier’s control. And yep, they have to pay up based on a domestic segment that’s part of an international itinerary.
It wasn't profitable until you actually receive the compensation. Good luck with that!
Good on you, Lucky, for pursuing UK261 compensation! Let us know how it goes.
Even a two hour afternoon/evening domestic connection gives me worry knowing AA. Why didn't you just get a hotel room, submit receipts to AA to see if they would pay and take something other than a 5AM flight?
AA for the most part isn't going to hold a flight-even last flight out. Sad but true.
@ George Romey -- To be clear, I like 5AM flights. I'm a morning person, so that timing wasn't an issue with me. :-) I'll have a separate post about my experience reaching out to American...
Agree, I don't expect American to hold flights, I just found it interesting in light of the recent announcement American made about holding more flights.
On Monday 14JUL I was to fly from SFO to DFW on AA, on aircraft N146AA (A321). It hadn't been flying the day before, and only came from maintenance an hour late to operate hour flight, which then diverted back to SFO due to pressurisation issues.
Two weeks after my flight, it had not been able to operate a single flight on schedule, mostly not operating at all and whenever they manage to get...
On Monday 14JUL I was to fly from SFO to DFW on AA, on aircraft N146AA (A321). It hadn't been flying the day before, and only came from maintenance an hour late to operate hour flight, which then diverted back to SFO due to pressurisation issues.
Two weeks after my flight, it had not been able to operate a single flight on schedule, mostly not operating at all and whenever they manage to get it up in the air, it was hours and hours late. What is wrong here?
Even after a several-day (maintenance?) break in Pittsburgh the plane just broke down time and time again. Now it finally seems to operate normally.
What 3 hotel options did American offer?
I had an AA flight delayed 16 hours in ORD. The customer service line was too long so I just booked my own hotel and contacted AA after for hotel and uber reimbursement - which they agreed to.
@ RK -- I wrote about the hotel options in this post:
https://onemileatatime.com/insights/american-airlines-overnight-hotel-offer-terrible/
But honestly, why is AA having so many issues with the new dreamliners? It's not like the seats haven't been on other planes before as QR has been flying them for a while now.
I would love to know exactly what the 'maintenance' issues are.
@ InceptionCat -- Yeah, I'm not sure what exactly is causing this, but clearly two of the new 787-9Ps have issues. I'm not sure if it's a Boeing quality defect, or if it's because the planes were briefly in storage, or what. I'm sure it's not directly American's fault, but ultimately a passenger's contract is with the airline, and the airline's contract is with the aircraft manufacturer.
You haven't been reading the news lately? Every new Boeing delivery, especially the 787, is fraught with problems as a result of their profits over product philosophy (the same one that is tanking AA as well)
I assume you're also entitled to the chase or amex travel delay protection that you have?
@ Omar -- That's secondary beyond whatever else is covered by UK261 regulations. In this case, I guess they'd cover the hotel if American wouldn't, but that's about it.
Yeah, that would cover hotel and meals, but (1) it’s separate from any UK 261 comp, and (2) since you can only use twice a year, I don’t want to use if the airline covers those costs.
In my experience the credit card coverage will cover clothing or other things that are not covered under UK261, or an expensive meal. I've even gotten a purchase of headphones covered for business reasons.
Wow. Your story sounded eerily familiar to me, until I looked back and realized we were on the same flight! Thankfully I had a (originally) 4 hour layover for my flight home to PHX.
@ Samar -- Sorry to have missed you, and happy to hear your connection worked out better!
90 minutes or less connection from an International flight is always pushing it. Too many little things can go wrong and then you don't get to tuck your kids into bed that evening :(
@ UncleRonnie -- For sure, though in this case, it was a two hour connection. Also, 11PM is way after my kids go to bed anyway. Also, this was the only flight that had availability, so I was ultimately happy to take it. If I absolutely needed to be in Miami that night, I would've taken an earlier flight. :-)
The way I look at it is there’s always a chance I’m going to make it; if not, then the airline/insurance will sort out a new flight and hotel for the night.
I wouldn’t book an overnight connection and pay for the hotel just because I think there’s a 10% chance I will miss the connection…
@Ben after being burned by short connections before, I’d rather not have the anxiety, even if it is a bit more exhausting.
Would have loved to say hi. Maybe next time!
@ Samar -- Hope to say hi next time as well! Regarding the anxiety of a connection that isn't super long, I hear you, but I figured worst case scenario, it would play out exactly like this (which isn't ideal, but isn't terrible, given the compensation).
I was in London specifically to review the Park Hyatt, and if I had taken the earlier 787-9P flight, I wouldn't have had time to have breakfast at the hotel, which is kind of a key part of a luxury hotel review. :-)
You can claim the cost of the hotel too. Have done it with Delta before when they offered hotels that I was not interested in and just sent them the bill. Not sure it would work if you used points though.
@ Mika -- So UK261 regulations aren't very clear on that. They say the airline is required to cover the cost of hotel, but doesn't clarify what happens if you reject the hotel that the airline offers. Some airlines are more generous in that regard, while others aren't.
Why is a brand new plane having soo many issues? Do better Boeing.
Boeing can't do better since they assemble the 787s in the MAGA state of South Carolina.
There's issues with the seats, it has nothing to do with Boeing..