United or southwest? Live in Chicago..

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Southwest. Companion pass, Midway has fewer delays and less traffic, if you can book business select miles are insane. If you anticipate lots of international travel or travel to BS fourth tier midwestern cities, then maybe United.

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United for Chicago 💯

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United. How is that even a question.

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Companion pass is super tempting

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I'm platinum on American and have a Southwest companion pass. The companion pass and Southwest miles are much better for domestic. I haven't payed for a domestic flight in 5 years. However, if you really want to cash your miles to fly around the world, then go with United.

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Southwest if you can get business select and short flights. Midway on Monday mornings is super short for precheck lines.

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If you live anywhere but north or northwest suburbs, probably Southwest and Midway. I actually like ORD better with status + precheck but Midway is easier to deal with. But I prefer both AA and Delta to United.

I live in lakeview so a bit worried about communing to midway

Lake view near LSD still pretty easy for Midway.

United - SW blows!

Southwest.

United. Nobody can hold a candle to the monster that is Star Alliance - plus, you get to eat stroopwaffles on your morning flights 💆‍♂️

Southwest. No one can beat the points redemption value.

Will this thread has not been helpful lol it's even!!

If you are traveling long distances every week and like international travel for most vacations, United wins. If you are traveling short distances (say <2 hours), regardless of frequency, you'll never get many United points. If most of your vacation travel is domestic or Caribbean, also go for southwest. If you have an SO you frequently travel with domestically - definitely Southwest.

C1 I think I'm going to go with SW.

I approve. Wait and see what city your next case is in and just confirm Southwest flies there direct, but at this point you can fly Southwest direct from Chicago to almost every tier 1 or 2 city in the US.

I'm in FS so generally will be traveling to some semblance of an urban center lol

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