Have to fly LA to Chicago for next couple of months. Trying to decide between Southwest into Midway and United into O’Hare. Thoughts from a status, points, and winter convenience perspective?

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Convenience, Midway. Not even close. Southwest better for domestic travel, United better for international.

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I did the opposite route for some time on United. Planes are always full but other than that no complaints. Also united miles are great for international travel as said above

What group are you in OP?

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If you can anyhow avoid -
never United.
Never ORD.
Spent nights there. They love to play the delay-delay-delay-finally cancel when no other option is available anymore game in the winter a lot

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Client is closer to Midway, if that makes any difference

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Thanks folks! I’ve been flying delta so far, think that helps me with international travel. I know O’Hare suffers terrible delays and they get worse in winter. Do Midway flights suffer similar fate in winter? I’ll also be getting status on Southwest in 2 round trips, while United will take me 6 weeks to get the first status tier. Probably gonna go with Southwest...

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It honestly matters, how ‘much’ closer is MDW? I fly SW and UA out of Chi, and both have great options, especially LAX/CHI. If you’re a Delta guy, I’d stick to one if you’ll be on this project long enough to reach status. Otherwise, might be worth flipping. Btw, UA has a nice status match/challenge

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Tough one. I happen to hate sw so I would do united at least one of the ways. No doubt that sw is faster. But consider some other aspects of the trip.

Do a status match and if you fly at slightly off times you might get upgraded or get offered a cheap $ upgrade. I think they used to fly some international planes with the lie flat business class seats ord-lax regularly but it doesn’t look like they do currently. Now they just use them for irregularities if you can get one of those especially Polaris, they are very nice. I like the sundaes.

Here are the three things that are good about flying sw/mdw.

-more on time
-can be faster to taxi to the gate at mdw after you land, faster to get into the city from mdw
-l’appitito and Riley’s daughter at mdw

Here are the things that are bad about sw/mdw

-people are more annoying (more occasional/leisure travelers, families)
-sw status is useless
-mdw security can be very very long even pre check, especially around the holidays
-sw makes you board the plane super early if you want a decent seat (have to get to the airport earlier, less time to get food, etc)
-mdw / neighborhood can be sketchy later at night

Good about ua/ord

-ord has frontera, publican, summer house, berghof, better lounges, higher end people (I’ve made some good business and personal contacts/friends at the lounges/bars at ord. Less likely at mdw)
-ua status will get you better seats, sometimes upgrades. Ua in general is much more comfortable than sw. can pick seats, get to the plane later, sit up front get off the plane faster
-ua points are useful and add up quickly for international trips. I take 1 international first/business class leisure trip with my wife every couple years easily. It’s so much more satisfying than getting a free flight on sw no matter where I’m going.

Bad about ua ord

-landing at ord can be a really long taxi to the gate if you land 10 right, traffic can be worse to the city (but depending on where you are going the blue line can be pretty good)
-slightly more delays out of ord

I would probably take ua both ways, but if I was going to switch it up, I might sw to Mdw as I hate the long taxi very much and if you are going to sleep it doesn’t really matter that you have to be on the plane early and then fly out of ord for the airport experience and comfortable ride on the way home.

helpful

MDW for convenience/time savings, ORD for points. I think it just depends on what you value more and your current status with each. If it were me, I’d take United.

Companion pass (southwest) is awesome . Use that savings to just buy an international ticket when required. Besides if you have their credit card you can just use points to get an international ticket .

FWIW there are nightmare stories with both airports. Midway *ran out of* de-icing fluid one weekend last winter. That said, I prefer Midway for its proximity to the city.

@P3 I save 10 to 15 minutes by coming in from Midway.
Unfortunately, Delta doesn’t have a nonstop to Chicago from LA. UA is just infamous for delays and cancellations which makes me want to avoid it as far as possible 😅

Another option is aa. I like the safety video. Funny

That’s super helpful P4!! Thanks, that’s given me something to think about. I hate long taxi time too and that’s making me lean towards SW. I’ll probably do status match as you suggested and try out UA until I have one terrible experience that completely turns me away from it 😅

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