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Southwest flight to Chicago

Posted on 5/14/26 at 8:52 pm
Posted by Gordon Hayward
Member since Jun 2016
1519 posts
Posted on 5/14/26 at 8:52 pm
It timed me out in the queue for the wanna get away flights and now is saying flights are twice as much but the preferred seats I picked are still available. Anyone else have this issue?
Posted by philly444
stuck in contraflow
Member since Nov 2008
12380 posts
Posted on 5/14/26 at 9:08 pm to
Gotta search flights in incognito mode and lock in those prices baw. The IT nerds on these airline websites are seeing which flights are getting the most views/clicks and upping the prices for those flights.
Posted by Gordon Hayward
Member since Jun 2016
1519 posts
Posted on 5/14/26 at 9:13 pm to
Yea I got got
Posted by Proximo
Member since Aug 2011
24144 posts
Posted on 5/14/26 at 9:14 pm to
I checked earlier today and can only find them for $400 roundtrip

It used to be $200 roundtrip back in 2018 to Chicago all the time. Sucks
This post was edited on 5/14/26 at 9:15 pm
Posted by bstaceyau19
New Orleans
Member since Jun 2022
1369 posts
Posted on 5/14/26 at 9:26 pm to
If you're going to Chicago:

Good morning, America. How are you?
Don't you know me? I'm your favorite son.
I'm the train they call the City of New Orleans.
I'll be gone 500 miles when the day is done.


Daily service in both directions between NOLA and Chicago. 19 hour trip each way.
Posted by htran90
BC
Member since Dec 2012
32290 posts
Posted on 5/14/26 at 9:47 pm to
quote:

It used to be $200 roundtrip back in 2018 to Chicago all the time. Sucks



Used to go there all the time, multiple United, SW, & spirit flights. Now there's barely any
Posted by biglosdaddy
south louisiana
Member since May 2007
1080 posts
Posted on 5/14/26 at 9:50 pm to
How about a nice train trip? Make a week of it?
Posted by Proximo
Member since Aug 2011
24144 posts
Posted on 5/14/26 at 9:52 pm to
Yep, ex girlfriend lived in Lincoln park and I went 10 or so times.

I did the really large Spirit seats in the front that were quasi-first / business class a few times and it was even cheap
Posted by ChestRockwell
In the heart of horse country
Member since Jul 2021
7643 posts
Posted on 5/15/26 at 5:23 am to
I may go to the Chicago game. Never been, but I heard horror stories about their fans. Its only a 4.5 hour drive for me. Will try and do Cincinnati the next week. The Bears game is the same weekend as LSU at Tennessee, so a decision has to be made. Neyland is a dump though.
This post was edited on 5/15/26 at 5:27 am
Posted by Townedrunkard
Member since Jan 2019
15055 posts
Posted on 5/15/26 at 6:10 am to
quote:

Used to go there all the time, multiple United, SW, & spirit flights. Now there's barely any


You can thank Joe and Pocohontas…
Posted by TeamCKennedy
Southern Illinois Baw
Member since Feb 2018
1687 posts
Posted on 5/15/26 at 7:36 am to
Same here. I am in southern Illinois near St Louis
Posted by jasonbr1975
Lafayette, LA
Member since Sep 2024
2025 posts
Posted on 5/15/26 at 10:56 am to
Amtrak is the answer
Posted by Delusional
Member since Dec 2018
6658 posts
Posted on 5/15/26 at 11:48 am to
quote:

Will try and do Cincinnati the next week


Cincinnati is a good time, not too expensive, and get to see Burreaux/Chase. The last time the Saints were there was a great game to say the least
Posted by LSUPilot07
Member since Feb 2022
8605 posts
Posted on 5/15/26 at 11:57 am to
Its a problem on Southwest’s side.
Posted by Combaro01
Member since Mar 2024
183 posts
Posted on 5/16/26 at 6:21 am to
Southwest site has been drunk lately lol. Same thing happened to me once, refreshed and suddenly the price doubled like I insulted their CEO or something.
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