[Update: New Chicago/ORD And Colorado Springs Routes Now On Sale!] Southwest Will Add Service To Chicago O’Hare And Houston Intercontinental!

en:user:DonFB [CC BY-SA 4.0], via Wikimedia Commons
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Update: Southwest will begin flying the following routes on 2/14:

  • Chicago-ORD to/from Baltimore (4 daily nonstops)
  • Chicago-ORD to/from Dallas-DAL (4 daily nonstops
  • Chicago-ORD to/from Denver (6 daily nonstops)
  • Chicago-ORD to/from Nashville (4 daily nonstops)
  • Chicago-ORD to/from Phoenix (2 daily nonstops)

They will also add service to Colorado Springs on 3/11:

  • Colorado Springs to/from Chicago-MDW (2 daily nonstops)
  • Colorado Springs to/from Dallas-DAL (3 daily nonstops
  • Colorado Springs to/from Denver (4 daily nonstops)
  • Colorado Springs to/from Las Vegas (2 daily nonstops)
  • Colorado Springs to/from Phoenix (2 daily nonstops)

Flights from Houston-IAH have not yet been announced.

Originally posted on 10/12:

Southwest announced plans to fly to Chicago O’Hare (ORD) and Houston Intercontinental (IAH) in the first half of 2021.

The airline has eschewed those larger and more expensive airports in favor of Chicago Midway (MDW) and Houston Hobby (HOU).

On the one hand, it’s helpful for operations to be consolidated in one airport in a region as you can fuel more connections that way. However it also limits purchases for origin and destination traffic when there is a strong preference for flights from another airport. HOU and MDW will remain major airports for Southwest, but operating some flights to IAH and ORD will open up new sources of revenue for the airline.

With United returning to JFK next year, it seems that the pandemic will continue to push airlines into more airports that they have been avoiding until now.

Will flights into IAH and ORD push you to fly Southwest in the future? Which routes do you think they will operate from those airports?

HT: Charles ORD

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23 Comments On "[Update: New Chicago/ORD And Colorado Springs Routes Now On Sale!] Southwest Will Add Service To Chicago O’Hare And Houston Intercontinental!"

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chicago goer

Sure! From mdw to the jewish area you have to go through the city traffic and its a major time consumer for daytime travel. Therefore I only do ord.

Texas Totty

But HOU is much closer than IAH in Houston.


Awesome. This helps alot!! Mdw is a pain for me

Dr Moose

Milts here we come!


Is it too early to schedule a DO?

Michael MDW

Just want to reiterate the hat tip to an absolute legend, Charles ORD


When I had companion pass my wife and I ventured out to MDW from WRP (west Rogers) all the time to fly around the country. Without traffic it’s about 30-35 min drive however when flying during daytime hours you’re sure to hit traffic turning the drive into an unpredictable 50+ min. We had a great parking garage that we parked at which closed down due to COVID. The drive to ORD is a consistent 25 min and always worth taking an Uber/Lyft. If they add some solid routes I would definitely go for companion pass again. Looking forward!!

Chitown man

Same. I didn’t enjoy the drive and it’s the reason I didn’t try for companionpass again. But if they start flying out of ORD, I’ll try again for sure.


“Which routes do you think they will operate from those airports?”

I expect the routes to be from SFO, DEN, EWR, IAD and GUM

Shmueli Heber

Southwest stopped flying from EWR about a year ago. I’m pretty confident they’ll fly from BWI which is a Southwest hub. I would expect routes from LAS as well, and perhaps BNA and MSP.


I know a lot of families in Skokie would sooner go to Milwaukee than Midway. Having done the ride on a vacation, I can confirm that it is terrible.

That being said, MDW is closer to the Loop area, especially if going by Metro.


Ditto on Skokie and add Buffalo Grove as those two villages are much closer to ORD than MDW. Why my family moved to South Barrington, I’ll never know…lol

Dave Hilfman formerly of UAL must be consulting for WN…

Routes? For sure: LAS, DEN, MCO, DAL, IAH, BWI and CLE (for Dan)



if they fly from lga or jfk (which i dont think they currently do) or even islip i would take that one to ohare over mdw
although i ma really waiting for lga to mke to come back


SW flights I bought during the 11/5-1/4/2021 free change period are now costing to change within the 30 day window. Is that an error or has SW changed the rules?


Yuck, I live in Chicago. I really enjoyed taking Southwest from MDW. I remember when Midway was pretty small and you parked your car outside of the main entrance sort of like a shopping mall. And parking was free. Back in the day, my mom and I used to sit in the parking lot watching planes taking off and landing (for fun).

O’Hare is such a hassle. And I have to use the expensive tollway to get there. And there’s going to be a steep learning curve. So many people are going to screw up and go to the wrong Chicago airport. Such a mess.

Raphael Rand

Will they be flying from Ohare to any of the NY airports? I see the list of routes, and NY is not on there…


I wish…


I would expect WN to add more business-centric routes from ORD to DTW, MSP, MCI, STL, CLE, CMH, CVG as business travel increaes.I don’t expect LGA on the list as AA, UA and DL fly the route.



They are still very cheap prices O’Hare LaGuardia via Baltimore


IAH is such a schlepp!