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My trip to Chicago for United Media Day 2019

Greetings! Last week, I flew from Los Angeles to Chicago for the night, as a guest of United for the airline’s Media Day. It was my first time flying United in over a year as I’ve been giving most of my business to American Airlines and its Oneworld partners to get the most out of my miles.

However, United will always hold a special place in my heart as it was the first airline I ever flew internationally (LAX-HKG when I was 23) and was responsible for getting me addicted to miles and points. I was United 1K (flew over 100,000 miles) for years, but about a decade ago, when I saw United going downhill, I jumped ship. I went to Delta and then to American, but after hearing all of the latest news and plans and meeting executives last week, I’ll be going back to United soon.

Here’s how my 29-hour trip to Chicago went:

My trip to Chicago for United Media Day 2019

Flying to Chicago

I took United’s 6am flight to Chicago. Early morning flights east always sound like a good idea when you book them because you arrive early at your destination and they force you to get adjusted to the time change. But the night before an early flight, I’m always thinking, “What the heck was I thinking when I booked a 6am flight?” By then, it’s too late.

I arranged for a Blacklane (I’m one of their brand ambassadors) car to pick me up and take me to LAX at 4:45am. I live 15 minutes from LAX and there was no traffic, so it was a breeze. One of the things I miss most about flying United is their employees. I formed incredible relationships with many of them (something I’ve never done with employees at AA or Delta) so it was great to see one of them again.

My trip to Chicago for United Media Day 2019

Fru, an old friend
Fru has been working at United for 50 years! She’s special and she gave me the VIP treatment when she heard I was coming. Once I cleared security (there was no line at TSA PreCheck), Fru was waiting for me. She showed me around the United Club, which is a huge improvement from United’s old Red Carpet Clubs. I wish I’d had more time to hang out inside, but boarding was at 5:20am. Fru offered me a ride to the gate in her “Fru Mobile,” and I couldn’t pass that up since it was a long walk to gate 84.

At the gate, there was a long line to board, and I was meant to board with Zone 3, so Fru escorted me onto the plane to guarantee I would have overhead bin space. It turned out that I didn’t need to worry about securing bin space because United doesn’t have those obnoxious in-flight entertainment system (IFE) boxes taking up space under their seats like AA does. That meant that my computer bag fit under my seat. And my overnight duffel bag was so lightly packed that I could’ve squashed it in no matter what.

The flight
I was seated in Economy Plus, toward the front of economy and with an extra four inches of legroom. The flight time was a short three hours and 20 minutes. I sat next to a cool Kiwi who works for the NZ government and just moved to D.C.

What most impressed me about the flight is that the flight attendants aboard actually looked somewhat happy and walked the aisles multiple times with a snack basket (stroopwafels, Biscoff cookies, pretzels) and trays of water (from the bottle, not the tap).

My trip to Chicago for United Media Day 2019

At Chicago O’Hare

United’s new CRJ-550
I landed in Chicago a few minutes early, just before noon. I walked from the plane to gate B1 where United was showcasing its brand-new CRJ-550 plane. At that point, I thought that the CRJ-550 was the main reason United was flying 100 journalists in from all over the world—but as you’ll see below, it turns out that it was only a small reason.

What makes this plane so special is that United actually removed 26 seats from it. The plane used to be the CRJ-700 but United rebranded it to make it arguably the most comfortable commercial regional jet in the world. It went from having 76 seats and little storage to 50 seats with enough storage for every passenger’s carry-on bag. Why would they do this? Some say it’s to save on paying for an extra flight attendant (the FAA requires one flight attendant for every 50 passengers), while others say it’s because United is trying to get around its scope clause with pilots.

Regardless of why, United passengers are the winners, since they’ll be more comfortable on this plane. Premium customers will benefit especially, as there are 10 first class seats and 20 Economy Plus seats. First class also has a snack bar, which is a nice touch. Yes, there will be less service, but these planes fly short routes (think ORD-YYZ) so it doesn’t really matter. I much prefer this set up and look forward to trying it out in the future.

ORD to downtown Chicago
Normally, I would take the Blue Line L train from ORD to downtown Chicago, but since I have a partnership with Blacklane, I had one of their drivers pick me up. I thought the way that ORD labels its parking garages was interesting. All floors are a Chicago sports team. I have to think that the approach makes it easier for users to remember which level they’re parked on.

As you can see my driver parked on level one, which is appropriately the Cubs.

The W Chicago – City Center

United put us up at the W Chicago – City Center, which is across the street from the JW Marriott. When the driver dropped me off, I initially thought that I’d walked into the wrong building as the doors make it seem as though you’re going into a restaurant/bar. It’s not your typical hotel lobby.

Check-in was quick. I got upgraded to a junior suite, probably because everything was sold out, I was only there for a night and I have elite status with Marriott. I like the hotel and its Bliss bathroom products, but the tub was old, the shower pressure was weak, and the walls and windows were too thin for my liking. I also don’t like heavy bedspreads.

But I appreciated that the hotel observed the “Do Not Disturb” sign when United wanted to send a gift up. Instead of knocking or calling the room, an employee left a note on the door.

United Media Day

United Backstage
I had no idea how big United Media Day was until I saw two busses outside the hotel and I sat next to a journalist from Israel. That quick encounter made my trip from L.A. seem like I’d traveled across town. The airline hosted a cocktail reception at its “United Backstage.” It’s a huge warehouse-type building where it’s been bringing in 800 flight attendants at a time to work on the new United. Oscar Munoz, United’s CEO, told us that United Backstage is not about training. It’s about engaging to talk strategy and to develop ways to help customers. So far the airline has had 21,000 flight attendants come in. Next year it will do the same and bring in more.

Employees here learn about all aspects of the company. We experienced some of it ourselves and more as United brought in outside vendors like CLEAR for the event. I learned a whole lot, from how United uses technology to help travelers and employees to how it tastes new food and snacks. Everything was off the record so I don’t have much to report, but I do have the photo above: Scott Mayerowitz and I testing out United’s jackets that ramp workers use in the winter.

United Media Day
The next morning we were back at United Backstage for breakfast and one surprising announcement after another. The event began with United’s Chief Communications Officer (CCO) Josh Earnest (he’s President Obama’s former press secretary so he’s a real pro) as MC. Josh began with a variety of safety instructions including “in the unlikely event of an active shooter…” When I looked surprised, a United employee sitting next to me told me that the airline begins every event with all of these instructions. Makes you realize that the USA is beginning to be a scary place.

Since this is getting long, I’ll shorten it up by listing some of the other highlights from United Media Day:

  • United is trying to be revolutionary when it comes to eco-skies. It’s made a $40 million investment and it’s made a goal of using alternative fuels. It’s doing the little things, too, like removing the plastic around amenity kits, which has saved 16 tons of plastic.
  • United is going to hire 34,000 people by 2023 including 4,000 pilots (if interested go to the website To be clear 40% of the 34,000 is growth and 60% is replacement with looming retirements. The team is expecting three million applications in total.
  • United says that if a customer is uncomfortable flying on the 737 MAX, it will re-accommodate them for no charge.
  • United COO Greg Hart told us about the ConnectionSaver app and how United pad its schedules so gate agents can hold planes if connecting passengers are a little bit late. Even if they have to hold the plane, the flight can still arrive on time.
  • Since United has been making money, it’s spending some of it on technology including an app feature called Soft Landing. It allows stranded passengers to book a hotel and get meal vouchers directly from a device instead of having to stand in long lines or make phone calls. It’s a win-win. Here’s an example tweet United sent out while I was at the conference: “We’ve issued a travel waiver for Santa Rosa, CA due to the Kincade Wildfires. If you’re traveling 10/27 – 10/31, you can change your flight at no cost on our mobile app, by direct messaging us here or calling Reservations at 1-800-864-8331.”
  • Speaking of technology, we heard about a cool feature that might make SeatGuru obsolete. United is beginning to offer 360-degree views of its cabins so passengers know exactly what to expect onboard. The first plane this is available for is the CRJ-550.
  • United has created Miles on a Mission, with which customers can donate their miles to partner charities or to a campaign created by users like a Kickstarter or GoFundMe.
  • United has launched a partnership with Marriott that lets Polaris passengers traveling between Newark (EWR) and London (LHR) have their checked bags delivered to their hotels free of charge.

    United has partnered with Star Wars: The Rise of Skywalker (in theaters December 20th) and will be promoting “safety in galaxies both near and far, far away with a new themed inflight safety video.” It also has a Star Wars-painted plane and Star Wars amenity kits for Polaris passengers (which were given to us).

I was really impressed, as were all the other journalists I spoke to, to see that United really is on the right track. One of the things I liked the most at United Media Day is that United is giving its employees the ability and power to make judgement calls and do something special. For example, if a traveler has to change plans because of an accident at home, an agent could waive the change fee. Or if someone is celebrating a milestone like a birthday or crossing the million-mile mark of flying, they can recognize that person or give them a treat.

Related: I took United’s Farewell 747 flight to Hawaii in 2017.


2 Comments On "My Trip to Chicago for United Media Day 2019"
  1. biz-traveler|

    Okay, I’m really struggling with “Media Day” and most of the stuff was off the record.

    Why, exactly do you have media day, and then embargo the information? Maybe hoping for favorable leaks and deniability if the feedback is poor?

  2. Cynthia Rankin|

    Hi Johnny,
    Great recap of your Media Day experience. While United’s new programs sound fascinating, we are very disappointed that they keep changing their frequent flyer program requirements. My husband and I have been loyal UAL fans for decades but are now thinking of switching to Hawaiian. They have upped the 1K requirement from $10,000 a year to $12,000 a year, then this year to $15,000 and in 2020 it’ll be $18,000! That’s fine for road warriors, but we are leisure travelers and spending $18,000 on air just doesn’t make sense. Plus, we very rarely get upgraded, even when using global upgrades. The poor agents who answer the 1K line said they are getting a lot of complaints. Bye Bye United!!!! Aloha, Hawaiian!!!!

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