United Airlines has rolled out a new digital ad campaign across Chicago, which it says spotlights its strong performance in 2025 but does so by trolling American Airlines with an “AAdvantage, United” quip.
United Trolls American In Chicago With “AAdvantage, United” Billboards
United sent me the images below yesterday, saying it rolled outs new digital ad campaign across 55 billboards throughout Chicago. These ads “spotlighting our 2025 operational performance and the strength of our ORD route network” will be live for this week only, coming down on January 30th.
Look for digital billboards around O’Hare and on the Kennedy Expressway, among other places.

The ads come in two variants, highlighting United’s stronger route map and schedule plus its superior operational performance from Chicago O’Hare:


View From The Wing says the campaign “feels a bit too on the nose to me, since United Airlines CEO Scott Kirby was directly responsible for much of the devaluation in the AAdvantage program during his time as President of American Airlines.”
He’s right that AAdvantage devalued greatly under Kirby’s tenure, but my reaction to this trolling (and yes, of course it’s trolling) is to chuckle….these days I fly often between Chicago and Los Angeles and speaking anecdotally (yet my own data set is fairly large): United Airlines tends to be on time and American Airlines tend to be late. Over and over and over.
The irony is that American AAdvantage is a better loyalty program than United MileagePlus right now, especially on the redemption side. That may further reinforce United’s success in being able to command a premium for its flights, whether paid with miles or dollars, but the difference are often stark…like United will be 4x the price of American for a similarly-timed flight on the same route. The reverse is never true.
United has teased big changes to its MileagePlus program and wouldn’t it be something if instead of just instant mileage earning on co-branded credit card spending (my prediction), it went all-out-AA in introducing a scheme like Loyalty Points to make status via credit card spending easier than ever before?
But back to the billboards: the message resonates and I think Chicagoans will take notice. It’s not that residents of the Windy City are blindly loyal to United (like those in more hub captive cities are forced to be), but United offers a better onboard product to more places and tends to be on time…that’s a big deal.
CONCLUSION
Following up on its Southwest Airlines campaign in Denver, United Airlines has once again chosen to troll, this time seeking to draw a distinction between itself and American Airlines. Ultimately, clever billboards won’t sell airlines seats, but this particular campaign is a reminder that there’s more than a gap in gates that separates UA and AA.
> Read More: Hilarious Billboard Battle Breaks Out Between Southwest And United In Denver



This whole saga is astroturf. No one cares about this. Unless and until there are serious deals for passengers, it’s all hype.
Still fun to watch this war play out 🙂
After all, the Windy City is UA’s proud home…
“Billboards are like outdoor theater; they speak to the world in a language of visuals.” — David Ogilvy —
Will AA sue United for using their trademarked name, AAdvantage?
United needs English lessons. It’s fewer canceled flights, not less canceled flights. Is United some foreigner that doesn’t speak English?
I do admit the ads are funny and that United is slightly better
To the attention of Maggie Schmerin!
United must have read your post because on my way to work today I saw that it now reads “fewer canceled flights”
I appreciate the effort/trolling aspect of this because it seems we are getting back to a point in the airline industry where there is some effort in distinguishing yourself from the competition……whether its more flights, better service, free/fast wifi, meals, seats etc…….but the execution seems very CO-esque and just looks and feels bland. That being said could AA sue UA for using the “AAdvantage” trademark in one of their ads?
As a former Chicagoan, I agree completely that Chicagoans aren’t blindly loyal — the majority of people choose to give United most of their business for both qualitative and quantitative reasons. In fact, it’s why when I started flying more on my own as a young adult, I decided to focus on United, and continued that preference even changing my home base twice to different spots around the country.
Do you feel that way about Hyatt, too?
Personally yes but not sure if that’s as widely shared amongst Chicagoans present and former.
Wait wait wait, has anyone actually photographed these billboards in action over the Kennedy Expressway? Because when you look closely at both images, the cars down below are in the EXACT same positions in both photos. What is being presented as evidence right now is the work of Photoshop.
Moreover, there are no leaves on any trees in Chicago right now. It’s the dead of winter. This is not current.
I am pretty sure this is fake. First, the cars are in the EXACT same spot in both photos. Second, there is snow/ice/sleet on the ground in Chicago right now…
United sent me these photo. They may be AI-aided or photoshopped, but they came directly from the source!
Its been below 20 degrees for about a week straight here, so i guess they didnt want to have some intern sit out in the cold waiting for their ads to cycle through…
“AAdvantage miles have value. AA is here to stay. See ya, MileageMeh.”
I’m sure someone in marketing can do better, but the problem with a snarky ad is it opens the door to the counterattack while portraying your competitor as a legitimate option (why have the ad if you are not concerned in the first place). If AA makes its counter iconic, changes the narrative.
So not a single person at either United or their ad agency knew that “less” canceled flights should be “fewer” canceled flights? That’s pretty sad.
If these are digital billboards, they should fix it.
Agree but I imagine the thinking was something along the lines of: “less” is the direct antonym of “more”, whereas “greater” is the direct antonym of “fewer”. “More” sounds better here.
A billboard! Did United steal that from Scott Bessent when he was on his way to a protest?
They fall on their knife, you pull a gun. That’s the Chicago way.