Southwest Airlines Will Start Selling Overnight Connections

Southwest will start selling overnight connection flights for the first time on June 26. They won’t offer redeye flights, but will use their current schedule to sell itineraries that involve an overnight at six airports – Baltimore; Denver; Las Vegas; Phoenix; Chicago Midway; and Oakland. Update 6/20/23: Southwest tells me, “the work has been delayed and we do not have sell date and we’re working on communicating this update to our Employees this week.”

No new flights are being added to the schedule, this just adds flight options to sell… that customers should be on the lookout for, because they’re options that many will potentially want to avoid.

Two examples where they’ll be selling an overnight connecting option are Honolulu to Houston and Seattle to Cancun.

Unaccompanied minors can’t book these connections. However passengers could also be re-accommodated on overnight itineraries during irregular operations, though passengers wouldn’t be forced to take this option if that happens.

This may be one first step in offering redeye flights, which Southwest hasn’t done before. Their reservations system now supports those. However I don’t expect it to happen within the next couple of years – Southwest doesn’t have the pilot capacity to fully utilize all of their aircraft during the day, so they’re unlikely to add redeyes before adding more daytime flying (although redeyes might first come to Hawaii – mainland routes).

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Let’s hope they upped the investment from last winter’s meltdown and aren’t just focusing on new revenue opportunities, but modernizing the entire approach to IT.

    Glad to see more competition is on the way in the airline industry, in any case!

  2. This is honestly great. So many times I’ve wanted to do caliornia-den-msp arriving den like 2am and going to msp 5am but the double pricing was crazy

  3. Flying SWA wasn’t treacherous enough! Now you can overnight with a Southwest passenger crowd in an empty airport!!

  4. Oh boy…what could go wrong, with technology that is literally paper clips and pratt glue. No thanks.

  5. @DougMac – my thoughts exactly, this is not a good change outside pricing. The only thing keeping them in my business is companion pass. A-List could keep me around longer but I really don’t enjoy my time on WN

  6. Current hours of operations are 3 am to 2:59 am. Apparently, they submitted a request to the FAA in 2013 to change the hours to 24 hours and were denied in 2015. Let’s see what they can do to operate redeyes.

  7. I looked to book SFO-DEN-MCO last month for mid july and I was told I would have to pickup my bag in DEN, hold it for 4 hrs and drop it off in the morning and go thru security again….no thanks. Hopefully they can handle a 4 hr and 15 min layover with these flights.

  8. Bring your pretzels from the flight because I can guarantee you that nothing in terminal 2 (Southwest) will be open overnight as OAK has a noise curfew.

  9. I don’t see this as something groundbreaking. Southwest has other pressing issues to remedy first. I travel for business weekly and I will not use SW anymore for one ways to California or other southwestern regions. They are trying to make up cash from the debacle they had last year and the flight one ways are almost double in some cases versus other providers. They have lost my business.

  10. They already do, they just don’t call it that. My last flight with them included an unplanned overnight stay in a fleabag motel in Dallas. Worst customer service ever.

  11. Southwest is hands-down my favorite airline. The friendliness from the stewards/esses, the leeway with late-boarding, the tiered pricing options, the free baggage, the seat-selection process which allows people who checkin early the same favoritism as rich customers… Southwest stands for friendliness and moral service. I know it’s popular (amongst the “travel crowd”) to hate on Southwest, but go ahead. It just makes my options on Southwest better.

  12. Good news for west coast travelers heading to the Caribbean. Now one overnight layover and we can catch an early morning flight to the islands.

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