I thought we had it all figured out: a cheap award flight from Cincinnati to Los Angeles, arriving just in time for an important convention.
Then Chicago weather hit.
Within a few hours, American Airlines had rebooked my family through Tucson, our connection looked impossible, and I was sprinting through O’Hare trying to save the trip.
Somehow, it all managed to work out.
The Plan: CVG to LAX for 9,000 Miles Each
I was flying with my 3 boys from Cincinnati to Los Angeles / LAX (via Chicago), on American Airlines. It was an early flight (leaving CVG at 6 a.m.) but would get us to Los Angeles early enough to hit the convention that we were attending as it started.

There is a direct CVG-LAX flight on Delta, which is what I booked last year when we went to this conference, but it was much more expensive. I booked this flight for 9,000 American AAdvantage miles each.
Chicago Weather Starts the Dominoes Falling
Everything started out fine – we got to the airport in plenty of time, though we didn’t quite have time to visit the new and improved Escape Lounge CVG. We boarded the plane and started to taxi out. At about 6 a.m. (our scheduled departure time), while we were sitting on the taxiway, the pilot came over the intercom and said there was bad weather in Chicago and they were holding us here in Cincinnati until 7 a.m.
We had about a 90 minute layover in Chicago, so I knew an hour of delay would make things dicey for our layover. We did end up leaving around 7:00, but because of the weather, instead of taking the direct route from CVG-ORD, we had to detour all the way around through southern Indiana. I never saw any storms on the weather radar (thanks, free Wi-Fi on American!) but I assume that they knew what they were doing.
American Rebooked Us Through Tucson. Seriously.
In the air, I got a notification from American that we had been rebooked on a flight leaving Chicago at 10:00 a.m., connecting through Tucson Arizona (!), arriving to Los Angeles at 2:15 p.m. This was not ideal since we’d miss some of the important parts of the convention that we were hoping to hit.

There was a direct flight from Chicago that left at 9:00 a.m., and I thought that it was possible that we could make that. It was weird because I was tracking our estimated arrival via FlightAware and sometimes it would say estimated arrival around 8:30, and sometimes it would jump to 9:30. A 9:30 CDT arrival seemed crazy if we took off at 7:00 a.m. EASTERN time for a 1 hour flight, even with a roundabout flight path.

I reached out to the Twitter team to try and get us moved the 9:00 a.m. direct flight. They were very nice but wouldn’t do it.

In the AA app, when the flight arrival time would jump to 8:30, it would let me rebook us automatically on the 9:00 a.m. direct flight, but then the arrival time would jump back and the AA app would automatically rebook us on a later flight. At one point, it rebooked us on a 5:00 p.m. flight from Chicago, which would have been horrible.
At this point I had reached that familiar traveler dilemma: Was I cleverly working the system, or was I about to make everything dramatically worse? (which has been known to happen before)
The Sprint Across O’Hare – 8 Minutes to Make Our Flight
We got to the gate at 8:52 a.m., and started making our way to the front. I had asked one of the flight attendants if they would make an announcement asking people without tight connections to let those that did have tight connections to get off first. They made the announcement, not that I think that really does much. Either people don’t hear it, don’t care, or have different ideas of what a “tight connection” means. The lady right in front of us had a flight to I think Richmond, and I saw on her boarding pass that it BOARDED at like 9:30. So that is a fairly tight connection with the delay, but I felt like telling her “listen, my flight is supposed to TAKE OFF in 8 minutes, can I get around you? 😀 ”
We were in row 18, and my oldest son (the one that was participating in the convention) bolted to the front – I think that he made it all the way to where he was literally the first one off the plane
(SEE ALSO: You Should Stand Up As Soon As The Plane Lands (Like I do))
Myself and my other 2 sons had to collect our suitcases out of the overhead bins, so we didn’t make it quite as far, but we did get a good ways to the front. We landed in the K concourse and the 9:00 direct flight was leaving out of H5.
I ran though the airport, eventually catching up to my son, and we went to the gate agent.
The Gate Agent Who Saved the Day
When we reached the gate, I fully expected the answer to be “sorry, the flight is closed.”
Instead, the gate agent smiled and said she could get all four of us on the plane.
Despite supposedly leaving in 8 minutes, they hadn’t even started boarding yet, so there must have been a delay here (sometimes the delays actually work in your favor!) She was very nice about it and helped us immediately. Of the 4 seats, 3 of them were middle seats and the 4th was an exit row seat (exit row middle, but still). I “volunteered” to take the exit row and schlepped my kids into the back 😀
As I mentioned, that flight was delayed a bit too – we ended up taking off at 9:47 a.m. and getting into LAX at 12:03 p.m., only about 90 minutes past when we would have gotten in.
The Bottom Line
In the end, we got to LAX only about 90 minutes later than originally planned.
The biggest lesson? During IRROPS, don’t assume the computer’s first rebooking is your only option. Keep an eye on alternate flights, be polite to gate agents, and if necessary, be prepared to run through the airport.
Sometimes a little persistence can save your trip.
We got to the convention a little late (our Lyft driver STOPPED FOR GAS on the way to Pasadena), but it all worked out. Being proactive and a little bit of airport running probably made the difference between arriving at 12:03 p.m. and not arriving for 2 hours later if we had just taken the flights via Tucson (though I saw the Tucson flights ended up getting a bit more delayed than that). I was grateful for the inflight wi-fi and also for having traveled enough to know how and when to be proactive.
How did we handle it? Any other recommendations for how to handle things when you misconnect? Leave them in the comments below
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at
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