Travel Deals

New Southwest Sale – Flights from Just $29 One Way (Sale Flights are Early and Late Flights)

a green grass field with a price sign
Written by Charlie

There is a new Southwest sale starting at just $29 one way – for those who take the early or late flights! Check out current reservations to see if you can save more!

This is one of the better Southwest sales of late with several city pairs on sale from just $29 one way! So, check it out and save some money or points! But, you will have to hit the early or late flights to save the most!

New Southwest Sale

Link: New Southwest Sale

Southwest Sale Details:

  • Book by 10/19 11:59 p.m. Pacific Time.
  • 21-day advance purchase required.
  • Travel valid 11/7/23-3/6/24.
  • Travel blacked out 11/17-11/22/23, 11/25-11/27/23, 12/21-12/23/23, 12/26-12/30/23, 1/1-1/2/24, 2/16/24, and 2/19/24.
    • Orange County (SNA) blacked out 11/7/23-1/2/24
  • Travel valid before 8 a.m. and after 7 p.m

Yes, that is a lot of blacked out dates, but just imagine the dates around the holidays as unavailable for this sale and you will be fine.

What is funny to me about this sale is that my home airport of Buffalo will often have deals at $39 from here to Baltimore with sales like this. However, this time it is at $69 with Buffalo to Chicago on sale at $39 this time and to Boston for just $49. While I like Baltimore for the proximity to DC, I like having Chicago cheap as well.

Then, if you head to the various hub airports (Baltimore, Atlanta, Chicago, Phoenix, Houston, etc), you will find some city pairs at just $29 each way.

One tip – if you have a choice, choose the early flight as opposed to the late option. The reason is that the late flights can often run late due to delays from that flight making its way across the country, Southwest-style. The early flight should almost always leave on time.

Check Your Already-Booked Reservations For Price Difference

So, now is the time to search for your tickets within this sale and see if you have a better price available now than when you had booked it. If the price has dropped, you simply select to change the flight and look at the same dates and flights again. Once you go through and confirm, you will receive a refund of the difference in miles and the cash for the taxes will be transferred for the new ticket.

In 1 Minute, You Can Have Your Points Back!

The whole process takes less than 60 seconds and you could save a lot of money or points! If you had booked your ticket in the past using cash, you will receive a refund in the form of a credit that is usable for 1 year from the time you originally booked the ticket. If you booked it with points, you will receive the points back in your account for the difference.

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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.