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Being in Chicago, your choices are functionally American, United and Southwest as the other options will increase connections.
United has historically had the best mileage redemptions of the three. Better value and route map (via Star Alliance). That gap is closing as the airlines devalue their redemptions more, but United is still better imo.
One caveat is that Southwest might be the best if you primarily want domestic/Caribbean travel, fly with kids a lot and/or have a partner that you will be able to maximize the Companion Pass with.
As far as experience/reliability go, Southwest has the perks of free bags but also a worse handling of IRROPS due to a lack of agreements with other airlines. UA/AA are largely a wash on reliability with United’s experience being slightly better — neither are great though.
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OP - once you’re a higher tier elite (Plat, 1K, or GS) on United, the experience is significantly better. They’ve done a good job, IMO, focusing on elite experience even though it may not be enjoyable without status or at lower levels.
Having had status with all 3 at different points, the marginal difference between the airlines isn’t significant enough to chase status with a specific one - all 3 have delays ~20% of the time and customer service will all depend on your luck of the draw.
Whoever gets you to your destination the fastest (nonstop) and has a hub where you’re based is the best option - for Chicago, it’s either AA or United, so then ask, where do you fly most often (e.g., Florida (AA), CA (United), East Coast (both work but AA is better b/c the JetBlue Alliance), etc?
Frankly, if I’m flying internationally, all 3 have very subpar products, especially compared to the Asian and Middle Eastern carriers. Delta’s hard product is better than the other 2, but not on every route - they have a subpar transcontinental product (NYC - SF, NYC - LA) which is the most important domestic route to have a strong hard product. Plus the product itself isn’t anything outstanding, it’s just not as bad as AA or UA - I’m not flying an extra stop or a couple more hours to fit their poor hubs into my schedule. If we’re talking loyalty programs, AA and UA again are far superior to Delta.
I’ve had a great experience with AA for five years now. Lived in Dallas and Chicago and SFO.
Kinda hate United.
At the end of the day, it seems like people have good and bad experiences on all of them and sometimes someone has a bunch of bad experiences on the same one.
They all have partners, and U/AA both have similar value status and redemptions.
All that to say, Chicago is good for U and AA. Pick the one that is also a hub city in the places you’re most likely to travel to or move to in the future.
Agree with D1 and P1. United is going to give you the best route coverage - united flies to a lot of international destinations itself not to mention *A. United also has the best million miler program. However AA does have better saver award non-stop domestic/international redemption rate (60k vs 57.5k in biz) we and last minute availability (14k vs 6k) tho
Lol fair. Remembered AA was trying to charge me $350 on BA fuel surcharges one-way biz when rebooking for a canceled AA flight
In the US definitely Delta - no question! But if in Chicago you reside in specifically, then might have to go with some-other airline since it's unfortunately not a Delta hub...
Rising Star
“In the US definitely Delta - no question!”
Is Chicago in the US? Asking for a friend
“But if in Chicago you reside in specifically, then might have to go with some other airline”
You will almost definitely have to go with another airline unless you want to connect through Detroit and Minneapolis on most of your flights.
Enough details for you, bud?
Just came here to say not AA. Was Exec Platinum with them for 3 years and the only thing they do best is cheap award redemption if you’re willing to take some inconvenient layovers half the time. Lost my status when I switched to Delta and I still have a ton of 500 mile upgrades I can’t access until I get some type of status back.
Delta platinum always treated me better than top tier AA. But since you’re out of Chicago, United would be your best bet.
Toss up between need for a direct flight or need for upgrades. What do you value more?
If you live at an hub, unless you are top tier, half the plane are elite status holders and you are never getting that upgrade - at least not that often.
I live in a United hub, but fly delta. Yes, I end up taking connections depending where I am going but my chances of an upgrades are in the high 70/80%. And I’m not top tier status at delta (diamond).
So, again, it’s what you want - time or comfort.
I agree with D2.. United and then southwest.. I'm done with AA
If you can’t make 1k or Exp on United of AA i would say southwest… Honestly if you take upgrades out of the equation (you will not get out of Chicago without 1k, and even then likely limited on m/thu gravel schedule).
For me I would fly southwest for good redemptions/earning and the flexibility plus midway is often easier to get to if you live downtown.
If you live out west or northern suburbs could change the equation a bit
Not entirely true. I've gotten many upgrades since mid 2019 even as a silver... just gotta pick the right fights not on m/thur schedule