5 Things You Should Know About Southwest Rapid Rewards

Screen Shot 2014-09-30 at 7.00.52 PMEverything about Southwest is different and there are many little details that you may not know about, that you could be benefiting from.

Here I’ll discuss, how to get bumped, how to get a good seat, how to lower your price after booking, and how to book routes Southwest doesn’t fly. Then I’ll show you how to hack the prices of Southwest tickets both by booking tickets to random cities and by booking flights to your connection city separately.

The art of getting bumped on a Southwest Flight

Southwest overbooks flights just as much as the next airline. It’s very often I’m boarding a Southwest flight and I hear the call, “the flight is oversold by two seats, and if anyone can take the next 3:25 flight you would get a Southwest voucher the price of your ticket plus $300.”

If you recall from my how to get free flights from getting bumped, Southwest has many of the same bump policies as other airlines. For example, airlines generally like people without checked bags. But I wanted to give some Southwest specific bump policies.

  • Arrive < 2 hours within scheduled arrival = $100 + price of flight
  • Arrive > 2 hours within scheduled arrival = $300 + price of flight

So if you had a $200 flight and if you landed more than two hours behind the flight you booked, you would get a $500 voucher ($200 ticket + $300 compensation). Thats per person.

It’s also a first come first serve system. You board and if they need you as a bump they pull you off. So go ahead and check with the counter early and tell them you’re flexible and didn’t check a bag.

And if you’re thinking, “but I always book the most undesirable flights because I always book the cheapest flights”. Well, book early (more than a month) and the prices are often all the same. Then you could choose the most desirable route. Also, you can often choose to connect through multiple different cities for the same price, since they seem to price by city pairs. Perhaps this will increase your chances of getting bumped.

Although perhaps the most desirable route isn’t obvious, but you can search flights going out this week to get a feel for desirable times/routes for your flight.

Take away: Get to your gate early just to add your name to the list, then go to the lounge.


How to get a good seat with Southwest

One of the most fundamental things to know about Southwest is that their boarding process is very different. Instead of being assigned a seat, you’re assigned a boarding position, then you pick your seat, much like you pick your bus seat as a kid.

The problem for us with this process is that getting a low boarding possition often means that we 1) may not find seats together, and 2) may not be able to find overhead space for our luggage (we never check bags). So the question becomes…

How do you get a good boarding position?

Much like their first come first serve seating process, their boarding positions are given based on when you check in. I often don’t think about my flight until I get to the airport which is why we’re often at the back of the bus (or rather; boeing).

However, you can checkin online 24 hours before your flight.

My trick for remembering to checkin 24 hours ahead of time

I put all my flights in my google calendar. Just a simple time and airport codes (i.e. “8:30 am ATL-CUN) on the proper dates. Go in to the calendar event and “edit” it to give an alert. Select email, and 1 day before. This will throw out an email saying that your flight is tomorrow at 8:30 am. Which could be helpful if you forgot the time, or which airport (like me in Warsaw). However, with Southwest, you will then know that it is now 24 hours before your flight and that you should log in and and just “check in”.

You can still print your boarding pass off at the airport after checking in online (we always use the kiosks). Checking in really just means that you’re still planning to show up to the flight. It only takes a few seconds and this method should work for you. Unless you’re like me and your email inbox is akin to a tidal wave.

Take away: Checkin online 24 hours before departure of your flight and get a great boarding group/seat with Southwest. Perhaps set an email alert in Google calendar.


How to lower your price after booking

Southwest is so awesome in that they don’t have cancelation or change fees. And they have an amazing policy and website for very easily refunding points/cash if your ticket lowers in price.

Now if it’s a cash cancelation or partial refunding, it will likely be a Southwest credit that is applied automatically to your account. Next time you go to pay for a ticket or even just go to cover taxes, it will deduct any cash payments from this credit.

But when refunding points, it instantly puts the points back into your account. And again, doing it is super easy.

Here’s how I look for better prices:

  1. Log into
  2. Open a tab to look at “upcoming flights”. This will show what are the flight times for my route.
  3. Open a new tab showing account activity. This will show how much you paid for each route.
  4. Search for the flight route/date you already booked.
  5. Compare current prices with the price you paid to see if it’s lowered.

You don’t have to only compare the exact same flights, but any flights. Different flights on the same day, or if you’re really flexible compare to flights on the other days. But in general I probably picked the flight I did because it’s the cheapest already and because it’s what I need. However, Southwest has lots of sales and it is very often that I find a lower price that I can match.

Once you find a lower price here’s what you do:

  1. Go to “my account”
  2. Upcoming Trips → “View All” (in the top right)
  3. For the flight you want to change, click “Change Reservation” in the top right
  4. Go through the booking process

It’s just like booking a flight the first time except you’re actually changing the ticket. If it’s a lower price then it will just refund the difference. If you decide to go with a more expensive flight, it will just charge the difference.

This user friendly experience is remarkable and Southwest deserves a lot of credit for not having insane change fees… or any at all.

Take away: Periodically check back in on the prices of your flight. If you see a lower price, find the original booking and “Change Reservation” and rebook to the lower price.


Routes Southwest Doesn’t Sell, but they do fly?

It’s interesting because if you look at Southwest’s route map, it will show blue lines to nearly every single location. Red lines are direct flights, which out of all the lines, direct flights are a small percent of the lines usually. But these blue lines show up regardless.

All the blue line means is that you are simply able to to book from one city to another. Well can’t you connect and go to every single city period?

Well, no.

For example, Southwest hasn’t started their flight from Chicago to Cancun yet. But they have started their flight from Atlanta to Cancun.

You would assume that you could type in Chicago to Cancun and it will connect for you in Atlanta, right? But no. My assumption is that Southwest doesn’t like to give people overnight layovers and since the Atlanta flight to Cancun is really early in the morning, they just don’t offer Chicago to Cancun.

Of course, you can go ahead and book a flight from Chicago to Atlanta, and then another flight the next morning from Atlanta to Cancun, but Southwest, for whatever reason doesn’t want to do that for you.

Perhaps the idea is that Southwest doesn’t feel it’s currently competing in the Chicago to Cancun market if it can’t serve you better, and that an overnight in Atlanta really isn’t better. And perhaps they will start flights that do better at reaching Cancun without annoying connections.

Take away Southwest basically allows every city to fly to any other Southwest city, with a few exceptions. And of those few exceptions you can still book the connection yourself.


Hidden Prices

Southwest is the oddest pricing system. In many ways it’s more logical than most airlines, and yet in many ways it leaves some hacks wide open.

The thing to know, which I’ve said, is that Southwest prices solely by city pairs. What this means is that when you look for a certain ticket, say Denver to Little Rock, it will be one price regardless of the routing. Of course the pricing system has other variables, mainly how full the flight is.

But all things being equal, Southwest will price a flight from Denver to Little Rock the same if it’s direct, if it’s through Houston, or if it’s through Chicago. The main calculation for price is based off the starting city and the ending city, and not the route.

This is a really funny effect, when Southwest has a sale from Denver to Little Rock and the tickets are suddenly cheaper than tickets from Denver to Chicago and cheaper than tickets from Denver to Houston. So in these cases, if I needed a ticket from Denver to Chicago or Houston, I could get off the plane and skip the last segment to Little Rock.

Now understand that when you skip a segment, the rest of the flight will likely be canceled. But if I booked a oneway, and it was the last segment I wanted anyways, it makes no difference.

That’s hack 5a. Got it?

Take away: if you’re flying to or from a hub, check for sales to cities with lower prices, that may route you through your desired city to get there.

5b is simply that it works both ways. Sometimes the city pair prices are higher than connecting through a city.

For example, I found that Southwest will let you book tickets from San Juan, Puerto Rico to Montego Bay, Jamaica. Prices were 13,300 points for a oneway that routed through Orlando. However, I then looked up each segment in oneways, and guess what I found?

  • San Juan – Orlando = 6,230
  • Orlando – Montego Bay = 3,290

In other words, the price of the ticket from San Juan to Montego Bay would be cheaper if both segments of the flight were booked separately. In this example you would save 3,780 points by booking these flights separately.

Take away: Southwest prices are city-pair based. In some cases, checking prices to/from the connection city separately will save you money/points.



Southwest is an awesome program. I can’t emphasize that enough. If you haven’t read How to Maximize the Southwest Companion Pass, you should. We are going to milk so many flights out of this Companion Pass. And that post breaks down all the fees of Caribbean destinations as well as points hotels in the Caribbean destinations. It is a resource.


Although the Companion Pass gets well deserved discussion, much of the other details of Southwest get overlooked. Yet, I have a feeling a lot of people are looking for an airline just like Southwest. So I hope you found at least one gem in this post. If you have any other details for Southwest, or tips that I should be using or investigating, please let me know.

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  1. Are you worried at all that hidden city ticketing may be dangerous to your Rapid Rewards account / companion pass?

    • I definitely have no problem with the practice, but I’ve always been under the impression that it’s not a good idea to link your frequent flyer account when planning to do so.

    • I have a CP and drop segments occasionally when I need to get to a specific hub (usually ATL). There are more risky things you could be doing with WN that are much more likely to put your CP in jeopardy, so I wouldn’t worry about a hidden city here and there. A few are easy to explain (you missed the flight, plans changed, whatever).

    • I’m not worried about it, but in reality there are very few times where it helps. So it’s not like all of my tickets would be throw aways. That would be worrisome.

  2. fantastic post! Great info, keep it up.

    Thank you,


    • Thanks PedroNY,

  3. Your blog is A+ material! Thanks for these. Love reading what you have to write as you bring so much to the table and don’t push credit cards 24/7. Hope you are having a fantastic time traveling the world!

    • Thanks Peter. Always appreciate positive feedback. For sure having a fantastic time. 😉

  4. 2 comments

    1) We almost got bumped on our Southwest flight out to BAcon, but the delay would have been 9 hours and we decided not to do it. There is some debate / YMMV as far as the “cost” of your ticket if you’re flying on points or on the Companion Pass.

    2) Families with kids under 4 board after the A group (first 60 people) which generally is enough to get seats together. Even our family of 8 was able to find seats (way in the back of the bus). Obviously this doesn’t help those without a kid under 4 :-)

    Okay I lied – 2 more comments

    3) If you use Award Wallet, and put your itineraries in, they will also send you an email at the 24 hour point to remind you to check in. But it goes FAST at the 24 hour point, so have multiple browsers open and ready to go if you can

    4) One thing that can help with finding a seat is finding which cities your flights originate in, and booking connecting flights. This only really works if you have a lot of flexibility in where you’re flying from (so not very many people). But an example is that our recent flight from MDW-RNO originated in PIT. So when we went to board in MDW, there were already a fair number of people that were already on the plane (Because they were flying PIT-RNO). Once the plane landed in MDW and all the PIT-MDW passengers got off, those remaining behind are allowed to move around to wherever they want.

    • 1) Yea man, 9 hours is a long time. But how much did they offer for your companion? I just assumed they booked in at $100, but it might be for the route or whatever. But the prices surely were not $100 when I booked.

      2) Good tip. Very family friendly.

      3) Forget about award wallet. Guess you could use tripit too. I just don’t use any of those. But good for anyone who does.

      4) I’ve actually had that happen, never thought of that as a benefit.

      You guys need to figure out how to get like 4 companion passes in one year.

    • At first she said they only needed 1 so they wouldn’t give any compensation for my companion (but would also put her on my later flight), but oftentimes the numbers of how many they need are fluid. I had them take my name off the list when my wife said she didn’t want to get into Vegas at 11pm

      As for 4 companion passes, I never thought about that – guess I need to get reselling more… 😛

  5. I can not tell you how much we are in LOVE with Southwest airlines. Easily the best domestic frequent flier program in the States. And their rewards are SOOOO cheap to change! 2 bags free! 10-minute no fee cancelations? WTF! Score!!!!

    • Yea, Carrie and I have been saying that every time we fly them. Actually I think we always say, “I love everything about Southwest! Except picking my seat like a childs school bus.”

  6. Southwest is the only airline that has consistently made profits. And their employees appear genuinely happy to be working for the airline. Who knows, maybe there is a connection between happy employees and profits? :-)

    Some bloggers at Boarding Area refer to Southwest as “Cattle Class”. Just fyi :-)

    • TBB I thought you knew all those gents over at BA are closet homosexuals.

      I’ve yet to see a single pic of Lucky or Gary on a trip with a woman (or any friend for that matter).

    • Hmmmm, you seem a bit too interested and focused on the matter. Also completely changed the topic to homosexuality. Begs the question. Nothing to be ashamed of though.

    • Southwest is also the only airline that doesn’t screw people for not being top tier (change fees). Coincidence? There’s got to be a connection between employee happiness/freedom and profits too. Less turnover, happier customers.

      I love being part of the herd I guess.

  7. With your steps for what to do when you find a lower price –
    what if the flight is the exact same flight, but just a cheaper price, do you still “change reservation” or just cancel & rebook?
    Also how do you handle international flights like Aruba, when it says you need to call them to make changes?

    • Yea, that is exactly what I do. I don’t actually change to different flights. I just want the flight I picked but cheaper. Same process.

      I guess I’ve never changed an international Southwest flight. Maybe those are AirTran convert flights. But I have no problem calling if it doesn’t work. Still no fee.

  8. The biggest problem with using Southwest’ Companion Pass is how expensive Southwest tickets have become — especially on “peak” travel days (non-Tuesdays and Wednesdays). I have a Companion Pass, and I barely use it. Avios awards on US and AA are far more lucrative.

    • It really depends on the route I guess. I find Southwest tickets for super cheap all the time. I look at points, 6,000 points or less. I guess that means it’s $100, but still cheapish.

      6,000 points for two can not be beat by Avios. But ymmv.

  9. 2 questions:
    1) what happens to your companion if you take a bump? can they still fly on the original itinerary?
    2) will WN give you an A boarding number for your new flight/s if you had one on the original flight?

    • Lindy- when we were flying to Las Vegas on WN the other day and I inquired about a bump, the agent told me that she only needed 1 but could accomodate 2.

      Meaning that my companion COULD have continued on the original flight, or she could have flown with me later (but would not have been compensated)

    • Exactly. Your companion gets their own ticket iten number, they aren’t actually connected.

      And when you get bumped they actually give you a ticket that’s like a paid ticket (at least with most airlines). So they rebook you into a normal ticket.

      Yea, they’ll likely take your tickets and throw em away and give new tickets regardless.

  10. Thanks so much for this info! I’m new to Southwest and recently booked a trip to Aruba. I was able to book 2 tickets using Wanna Get Away fares, but for one, I had to book an Anytime fare on one leg. I assumed that all of the Wanna Get Away fares were sold old but your post prompted me to check and indeed, a lower fare was available – save me $75. Thanks!

    • Awesome! Immediate pay off. 😀 Hope it had a decent savings.

  11. I’ll echo the sentiments above about compensation for a bump when booked via points. Seems every time I’ve been bumped or offered a bump when booked using points (or using a companion pass), the standard offering is always $100 + $300 – regardless of the amount of points used for the booking.

    • That’s really odd, I was just offered the price that the award would have been ($200 some + $300) on an award ticket and $100 + $300 for the companion ticket.

      Hopefully I’ll get to try again soon.

  12. I once came closer to getting bumped. But no luck. Was really hoping.
    Great post, by the way, Drew.

    • Thanks

  13. The hidden city pairs is a fantastic hack but I think even more importantly is Southwest still allows you to convert points to credits by routing through AirTran and then back again to Southwest. This caps many (not all) round trips at 19,200 points. I’ve used this heavily for East Coast/West Coast flights that are ~$400+.

    • Yea, and there are still some flights to the Caribbean that take you over to Air Tran. But that’s a very good point… I should have included that here, but I’ll just have to do another SW post sometime soon. 😀

  14. I just want to say that you 2 are doing God’s work here at Travel is Free.

    • lol
      Thanks Ramsey

  15. First comment :)

    Dude, two words: Tripit Pro. I’m sure you have a barclay card so it’s free to get a membership. They’ll send you a 24 hour check in reminder (email and/or text) with a link to check-in with pre-filled confirmation number so within 2 clicks you guarantee yourself a high A or low B :)

    You’re way too sophisticated of a traveler to be using Gcal for 24 hour check in reminders haha. Yes that is a compliment, keep up the good work. I’ll be reading..

  16. One place to always check for hidden city deals is when Southwest introduces service to a new city. Usually there are discounts from that new city to other cities in the Southwest system.

  17. old post – just stumbled here

    i have been flying delta almost exclusively as they always stick to their times and have great service in general. Southwest/ airtran has been picking up similar flights (less flights available) – do you recommend flying southwest over delta if prices are similar or do other factors come into play?


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