Bypassing Southwest for a Premium American Airlines Connection: My Business Class Journey to Chicago

I recently wrote that I won’t buy Southwest Airlines flights where they aren’t selling Early Bird check-in. Now that I no longer have Rapid Rewards A-List status, I need a way out of a middle seat. And the odds I’ll hit checking in at exactly 24 hours out are low, plus that’s not even a guarantee.

Out of Austin, Southwest actually had the best schedule for me to fly to Chicago. When I booked this trip there was nothing between 8:20 a.m. and 3 p.m. on American. I didn’t need to be in before dinnertime, but I did need to be there for dinnertime. And I didn’t want to leave home before my daughter left for school just to take American. Southwest was out because their mid-morning flight to Chicago Midway wasn’t selling Early Bird. And United’s mid-morning flight doesn’t operate daily.

So I settled on an American Airlines connection from Austin to Dallas to Chicago.

  • It didn’t really add additional distance to the trip
  • The Dallas – Chicago flight would be on a Boeing 787-9
  • And there was confirmable upgrade space into business class on that 787!

I used a Business Extra ‘BXP1’ domestic upgrade certificate to confirm my international business class seat on this two hour domestic flight. The loss of Business ExtrAA in a couple of weeks, which is being replaced by the far inferior AAdvantage Business program is really sad. I’ll miss confirming upgrades this way.

Meanwhile, my upgrade for Austin to Dallas cleared at the 100 hour mark, something quite rare these days but also not surprising following the long Thanksgiving holiday.

I left home around 8:50 a.m. for my 10:20 a.m. Austin – Dallas flight that was showing on time. TSA screening took an especially long time. The lanes without the Analogic scanners were all closed, so even without a backup of passengers PreCheck took more than 15 minutes as they were processing backs through the checkpoint slowly. (Pro-tip: whenever there are lanes with the Analogic machines and without them, always take the lane without them even if it appears to be longer.)

Then I headed up to the Admirals Club for just a few minutes, before heading down to the gate. Though I wouldn’t have a meal on either flight I skipped what they call breakfast in the lounge.

The agent there was a bit overwhelmed by a full flight, even though it was just a regional jet. She had to assist the crew in getting the lav services after having called for the start of boarding and just became flustered. I know that employing only a single person to board a domestic flight has become de rigueur but two makes travel so much smoother.

I do not mind Embraer ERJ-175 regional jets at all (except that most have slow air to ground wifi, even though high speed satellite is now possible) I do not much like similar-sized Bonbardier CR7 and CR9 planes. That’s because their overhead bins do not accommodate standard carry on bags. So you can carry your bag on, sort of. You drop it off on the jet bridge, and it’s returned to you there when you deplane. Only passengers line up in a long queue down the jetway, and it can take awhile to get yours as one comes up at a time – precious minutes when you’re on a short connection.

It turns out we came in onto the E concourse in Dallas, and not just E but the American Airlines E satellite gates. I’d actually never flown out of those before. You cave to walk to an underground tunnel to reach the main E concourse before making it onto the Skytrain to change terminals. I was heading from E satellite to E to D36. D is the international terminal, but some domestic flights leave from there, and it’s generally where widebody aircraft will depart from.

I made it just in time for scheduled boarding of my flight to Chicago, but the gate actually started boarding two minutes early. Cabin crew weren’t allowing passengers on yet, so there was a long backup on the jet bridge for my second flight even though I joined the queue before group 2 was called.

I had chosen seat 1L for the trip, the bulkhead seat in the first row on the right side of the cabin. That is more or less the most private. You’re angled facing the window and really don’t see anyone else. However I could hear loud galley gossip throughout the flight.

On American’s 787s you can’t use any floor storage so my laptop bag had to go in the overhead bin. No big deal, though I do prefer it within arm’s reach.

These 7 year old seats still hold up reasonably well. They’re a mostly off-the-shelf Super Diamond seat that’s popular with many top airlines. Qatar Airways uses it on a few aircraft. British Airways uses it, but added doors and a lot of bespoke design, for their new Club Suite.

American’s 787-9s have this seat. Four of their 787-8s have it. And about 60% of their Boeing 777-200s have it. The rest of those planes have ‘Concept D’ seats. My biggest complaint is that they didn’t install dividers between the center seats. That was their solution, I guess, to the dividers getting stuck on their previous (Concept D) seats. But it means there’s really no separation or privacy for solo travelers seated in the center section. I was in the window.

There’s a large, accessible lavatory between the business and premium economy cabins.

Predeparture beverages were offered, though just water, with a flight attendant explaining that they were late-catered.

Once we were in the air I fired up my laptop. American wanted $19 for one hour of internet, or $25 for the full flight. Their widebodies are served by Panasonic, and monthly wifi subscriptions are only valid on Gogo and ViaSat-equipped narrowbody aircraft. Still, I paid it so that I could work.

Shortly after drink orders were taken, and a snack basket was passed. We arrived after 3 p.m. local time, and I hadn’t had an opportunity for lunch. So the snacks were something, I guess. Dallas – Chicago is over 800 miles. That’s shorter than American’s meal threshold. But a hub-to-hub flight like this one ought to have something more substantive.

Ultimately though – limited inflight service on a short flight aside – there’s really nothing like flying a widebody domestically. It has premium economy sold as coach and business class in place of domestic first. Short haul flying between major cities in Asia is often like this, but widebodies U.S. domestic are far more limited – something that didn’t used to be the case when I began flying for work years ago. Along a certain margin I’ll go out of my way for it, though certainly more so on longer flights than on short ones like this.

I wouldn’t normally connect flying between Austin and Chicago but for this trip it worked out perfectly.

On arrival, I stopped at Tortas Frontera, the only really great food option in a U.S. airport to pick up a choriqueso that I’d eat once I made it to my hotel.

My flight arrived in Chicago early. It wasn’t that inefficient to connect in Dallas, considering my schedule options. It was far more comfortable than flying Southwest in a middle seat. And I got the chance to fly in an American Airlines international business class seat for the first time in quite some time. So I was happy!

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Sounds like it all worked out really nicely, that’s awesome! If only you had a longer layover in Dallas you could’ve enjoyed another visit to the Cap 1 lounge 🙂

  2. I do wish AA would do full service meals in first for all flights over 2 hours.
    A 2 hour flight still requires at least a four hour time commitment so a meal would fit right in.

  3. Gary can you comment on your in-flight internet experience?

    I see a lot of bloggers and commenters talking about paying for in-flight internet, but my experience has been that regardless of aircraft or provider the speeds are horrifically slow – For those of us who remember dial-up, slower than that! It’s near impossible for me to justify paying for that service (particularly on a shorter 2-hour flight) when I know I’m going to get 15 minutes of work done in 2 hours due to all the time spent waiting for pages to load or files to download/upload. I must be missing something…what am I missing?

    (Genuinely, not just trying to be on my soapbox, I really want to understand what I’m missing?)

  4. This is one place pre-pandemic Delta had a leg up on the others: They usually added meal service on somewhat-shorter hub-to-hub flights (I know ATL-DTW had meals, and I think ATL-JFK did as well).

    [It’s particularly relevant for folks who pull a two-stop flight with short layovers on each end of the main leg.]

  5. Does Gary ever respond to these questions? About the only time I have seen him respond is during the “troll debates” when he refutes / clarifies something that was said. Very rarely do I see him answer run of the mill questions.

  6. I’ve used my monthly AA wifi subscription on widebodies including a B777 about three weeks ago (domestic flight). Did I somehow pay and never noticed it or is it working now? I recall the sign in process wasn’t as straight forward as normal.

  7. I’ve always liked the E70/75 better than other regionals, but the last time I flew, on an AA (I believe Envoy), the overhead bin wasn’t big enough for my carryon. I was surprised, because it wasn’t even a max size carryon. I’ve been able to use the overhead for a normal carryon on UA and DL E75’s though.

  8. Patrick I have to admit, I have noticed that as well. It’s one of the reasons I don’t engage in the comments section very often. I’ve always assumed Gary checks for a few hours before moving on to the next post (He surely can’t follow every post indefinitely) and was hoping to get in early.

    But broadly, it would be nice to have a little more engagement beyond the occasional clarification that some accusation someone made was inaccurate.

  9. Didn’t AA used to do meal service on ORD-DFW/LGA/DCA? I’ve taken all those flights in the past and could have sworn they all had full meals on mainline.

  10. @Jeff – I suspect that on this short flight and at these prices not many people bought it, so there was enough bandwidth for my use and it was quite acceptable.

    While Panasonic generally doesn’t perform like ViaSat, American has experimented with more bandwidth on some aircraft. In this case I suspect it was just no one else was paying the high charges.

  11. I’ve flown Souhwest several times and received boarding group numbers deep into B and sometimes even in C and almost always gotten an aisle or window. dont be so presumptuous.

  12. @shaun You’re correct those were all “exception” markets that used to have meal service. None of which have been restored post-covid. I know UA provides meal service ORD-DFW.

  13. Why would you PICK a middle seat on Southwest???
    If you fly southwest set a reminder on your phone to check at the 24hour mark. I’ve never been in B or C doing this

  14. Altho it’s true that even If you check in at the exact moment you’re allowed to check in on Southwest, you’re very likely these days going to be in the B group, I’ve never had to take a middle seat on Southwest. Ever. I don’t see why this is such a big deal for you. Set your phone alarm and check in.

  15. I’m not flying LUV again until they have upgraded ALL of the systems that failed last xmas week, and we have seen those systems function through a minimum of 10 heavy holiday periods,, which is a minimum of 2 years from the date all systems have gone live, and they are nowhere close.

  16. Thanks Gary, most of my travel on American is 90-minute flights and my experience with wifi has been pretty poor, but I also use the “free T-Mobile” option so maybe actually paying the fee puts you in a premium tier. Either way thanks for sharing perspective, I may give it a shot next time I’m on a business flight and can justify the cost.

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