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Southwest airlines and flying into midway

mh, 5 month old daughter and i are taking a trip to chicago in august.  I was just going to book our tickets and of course the price went up on united.  so after some searching we can save $100pp  on southwest, but we've never flown on them.  how are they?  also southwest only flies into midway, is that relatively close to chicago compared to o'hare?

Re: Southwest airlines and flying into midway

  • i lived in chicago for three years and i don't remember if i ever flew on southwest but i will tell you that midway is much closer to downtown chicago than o'hare is.  both are big airports but i hate o'hare...just so congested.  have a great trip!
  • I don't fly Southwest but I know people that do. They never seem to have any complaints about them. Plus if they keep flying with the same company they can't be to bad.
  • I believe the train goes out to Midway, so worst case scenario you could always take that into the city.  As PP said, Midway is much less congested than O'Hare...
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  • (I lived in Chicago for 5 years)

    I LOVE Southwest and I LOVE Midway. I have made it from the train (which goes right from the Loop in about 30 minutes) through security and to my gate in less than 10 minutes. It's such a small airport and Southwest (and a few other small airlines) are the only one that fly out of it so the security line is always pretty small.  

  • I live in Chicago and mostly fly Southwest because their prices are the best.  Southwest is fine, there are no tv's or luxuries but I believe you still get a (very small) free snack.  It is a row in the center and 3 seats on either side.  The only thing I don't love about SW is they don't assign seats.  You are assigned a letter and number and then you line up to board according to that and sit in any open seat as you board.  I believe they let parents with babies board first.

    I would recommend a sedan to get downtown if you arent traveling during rush hour.  I hate the trains in Chicago, but thats just a personal preference.  Depending on the time of day the traffic can be horrific going into the city from both airports, one isnt really better than the other.  But Midway is much smaller and easier to get around than O'Hare.

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  • I like Southwest - the boarding process is easy and quick, and I find that the flight attendants are so much friendlier than the other domestic airlines. Plus cancelling/changing flights is so much easier with SW (if you ever need to do that).

    I have flown into Midway via SW a few times. Airport is way less crazy than O'Hare. Plus taking the train from the airport to downtown Chicago is super easy.

  • SW is wonderful :) I pretty much only fly them and I fly often (12+ times a year, about 25% of those flights being to Midway). People traveling with children 3 and under board between Groups A & B. I DO NOT recomend taking the El (the train) out of Midway after sundown. The Orange line is very rough at night. Especially if you are with children, spend the exta money on a cab. Depending on where you are staying, it's not necesarily closer than O'Hare. O'hare gives you easier acces to the North Side and also the 'burbs. Midway is on the South Side and you have to go through nasty loop traffic if you fly during rush hour. But Midway in itself is not a bad airport. Have a wonderful time in Chicago!
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  • We flew Southwest for the first time last week (Midway to SFO and then home again), and I wasn't a huge fan. Saving on airfare and getting free checked bags was nice, but coming from elsewhere in IL, O'Hare was actually a closer drive for us. I've also flown out of O'Hare probably close to 25 times and thought it was much easier there. Because it's such a big airport, each major airline generally has their own terminal so security and checking bags typically went faster there than at Midway, at least in our experience.

    Flying out of Midway on Southwest was OK, but coming back it was awful. Might have just been SFO though. We paid for early bird, which automatically checks you in and lets you have a higher group number, but the employees at SFO were handing out pre-boarding passes willy-nilly (supposed to be for those with disabilities or other needs for pre-boarding), plus people were blatantly announcing they were saving seats for people in like C group and the employees just let them do that. I felt our money spent on Early Bird for that flight was wasted and the boarding process was chaotic. However, the experience at Midway was a little better, so again, it might just have been SFO.



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  • I fly southwest from DAL to MDW  and back almost every month.  The flight attendants are nice, the flights are rarely late and will sometimes even leave early.  If you are checking any bags they are free.  They allow families with children to board between the A and B groups.  It is not worth paying the extra for early check in just make sure you check in as soon as you can, which begins 24 hrs before the flight leaves.

    Midway is much smaller and easier to navigate than O'Hare.  There is a train from midway to downtown Chicago.  If you drive it is about 30 minutes depending on traffic. 

  • HI! I Live there! And I love Southwest and I love Midway. I only fly into Ohare when I really have too. But I have flown them at least once a year since I was 8 and I am now 24. Midway is awesome and so is Southwest and they save you major cash!! Especially on the the free checked baggage! Good luck! Hope you have a good exp!
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