A Retro Continental Ride to Chicago (Trip Report)

United asked me to come speak at its commercial leadership team event in Chicago earlier this month. While Iʻm normally skeptical about doing these kinds of things, I was curious enough to hear how United internally presented to its team to make the trip. It was worth it.

I’m sorry to say it was all off the record, but I can share this photo of me in one of my ridiculous Cranky Network Award jackets while talking to United CEO Scott Kirby. Caption this one in the comments…

Though I can’t talk about the event, I can talk about my flights. United was graciously willing to fly me out in First Class. I was hoping to experience the newest United has to offer, but instead I ended up with a retro trip in both directions. Today, I’ll talk about the way out. I never had the chance to fly Continental in First Class, so this was as close as I’ll get.

[Disclosure: United provided flights, hotel, and ground transportation for this event]

I had originally booked my flight out to Chicago on the A321neo. This is Unitedʻs newest aircraft, and itʻs also the one that people seem to rave over the most (domestically). Unfortunately, when I looked a day before travel, it had been downgraded to a 737-900ER. Iʻm not sure if that happened in a schedule change at some point or if it was a late substitution, but this flight seems to bounce around between a ton of different aircraft types by day. Oh well, this meant, no United Next interior for me this time.

I had taken advantage of United’s meal pre-order option online and chose the scrambled eggs for my 8:15am departure. I made sure to put the United app to good use since I only hear positive things about it, and I didn’t really use it except to check in for my trip to Honolulu in September. After playing around with it, I have to agree that it really is the best airline app around. The amount of information available in there and the general functionality is just so good.

I was traveling on Veteran’s Day so it was smooth sailing up to LAX in my rideshare. Then it was gridlock in the horseshoe, mostly because I made the mistake of traveling on a day ending in “y.”

I strolled into the terminal around an hour before departure. The signs were again up everywhere touting the mobile driver license option, so I hoped I would finally put it to good use.

That did not happen. The TSA Precheck line was long, but it moved quickly. When I got to the front, the agent said that the mobile license doesn’t work. WHY DO THEY HAVE ALL THESE SIGNS?!

I made my way back to gate 75A which is wedged into the west side of the terminal and has very little seating. I found a quiet little corner where I could stand and stare out the window at our aircraft. There was a lot of gate lice in the cramped gate area, but since I was in group 1, they weren’t in the way of boarding.

United 2039
November 11, 2024

Onboard, I grabbed my Clorox wipe from the flight attendant and then realized I was in a time warp. These were some big, bulky, old Continental seats with the DirecTV seat back screens. They still have the credit card swiper there, but I decided not to test and see if someone had installed a skimmer.

The seat looked really comfortable, but it wasn’t. I’m not sure if the padding was just worn or what, but it just didn’t feel quite right. I didn’t notice it after the first few minutes though.

We boarded on time and were ready to go early, but we didn’t move until our exact departure time. The flight attendants had come through with water or orange juice, and then they did a manual safety briefing. I guess these old screens don’t play anything but live TV, but hey, at least they worked.

We were soon airborne, and we pointed toward the northeast for our flight to Chicago. It was a beautiful morning, but there was some light chop on the way up. I was feeling exhausted, so I closed my eyes, but there was a gentle tap on the shoulder a minute later. The flight attendant confirmed that I had ordered the scrambled eggs, and service began.

First, a hot towel was handed out. Then I was brought my first drink of the day… and Aha Blueberry + Pomegranate sparkling water which was a really nice change from the usual sugary sodas.

I opened my tray table to find it busted. It was very wobbly, dipping to the right and moving around loosely whenever I touched it, even lightly. The flight attendant said he’d write that up.

The eggs were fine, the fruit was passable, and the warm roll was good. But the hash browns were mushy and had a weird oily taste. I didn’t eat the rest.

Then it was time to get some work done. Like on American, T-Mobile gets you free wifi access on your phone but not on a laptop. But unlike on American, I didnʻt have to mortgage my house to pay for the service on my computer. It was a completely fair $8.

Streaming wasnʻt going to work at this speed, but it was quick enough for me to get work done. I cranked away while watching Goldfinger on BBC America… until they interrupted us with a credit card pitch. It still feels cheap, no matter who is doing it.

We descended into Chicago from the north, went out over the lake, and then circled south back to the west. It was a somewhat hazy day, but that doesn’t dampen the excitement I get every time I see that gorgeous skyline.

The flight attendant came through the cabin to thank everyone individually for flying United. He didnʻt use names, but it still felt sincere and I appreciated it. Just before landing, I got a glimpse of the behemoth that is O’Hare.

We landed on runway 27R which is the northernmost runway, nearly in Wisconsin. It was an 18-minute taxi until we finally nudged into our gate. The retro theme continued when we parked at an E gate in Terminal 2, the terminal that time forgot. (I particularly love that STAIRWAY sign.)

It’s just as I remembered it from when I worked at United 20 years ago with low ceilings, narrow corridors, and a McDonaldʻs shining like a beacon of familiarity at the base of the Y where concourses E and F split.

The only difference from when I was there is that now that United tends to be a better airline, there aren’t refugees lining the hallways, waiting for flights that will never leave.

I noticed walking out that there are almost no ticket counters in Terminal 2 anymore. Theyʻve largely been removed, presumably since itʻs mostly occupied by United and they want everyone checking in at Terminal 1. But there were still a few hanging around, like for Air Canada.

I found my rideshare out the door and then headed out into traffic on the Kennedy Expressway to go into town. I thought United’s service was great, the food was good, and the seat was ok. I really look forward to trying the A321neo at some point.

The event was at the JW Marriott in the loop, and thatʻs where I stayed. It was an action-packed couple of days, before a different kind of retro experience would bring me home.