What’s your dates?
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This is my strategy with Southwest. I’ve stalked the site over the years. For domestic travel, not immediately around a major holiday, the sweet spot starts at about 105 days out. I book on a Wednesday. I like the new Wanna Get Away Plus because any points refunded or travel credits issued from modifications can be transferred to one person. This is handy when I’m treating airfare to people other than myself and my husband. If I save $$, I want the travel credit back to my or my husbands airfare. It’s only $20 more a ticket but a few more points earned per flight. And I always pay for early bird so I watch the Anytime fares as well. Sometimes once you add that in, Anytime is just a few $$ more, comes with more points earned AND Priority/ Express Lane access. That is sooo handy at certain airports.
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Feb. 29 - Mar. 8.
I just booked our flights. I was able to use points 3 of the 4 parts. I had to book one of us round trip on points. Then I booked the trip back on points for the other. Finally, I had to book the trip there using dollars, since I didn’t have quite enough miles.
It is a little annoying that it doesn’t have a way to do this and keep us together in the system, but whatevs!
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Did you price out booking one way vs round trip? Sometimes one side will reduce but the other could increase, wiping out the savings. This happens a lot to me with Southwest. Not sure if Delta is the same though. I usually book one ways only.
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You should start to see that fare come down in November unless the flight is near full. I know you can’t see seats that aren’t pre-picked but that could also give you a good indication of how the flight is looking.
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Delta doesn’t seem to do that…at least not each time I have checked. The round trip costs the same as booking each segment one way.
But…I did make sure I selected the cheaper of the two directions for the ticket we are paying cash for. All said, with taxes and such, it will be $306 for both of us to fly to/from Orlando.
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That’s not bad. And maybe it will come down. That’s around the bottom we pay for round trip from MSY but I would think from your home airport it could easily be double or triple even. Although I would much rather be flying Delta than Southwest! My boss just took Delta to Venice. First time flying Delta (Delta Comfort +). He said it’s the best flight he’s ever been on with the exception of maybe First Class.
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There is so much info here; so forgive me if I’m bringing up what’s already been answered.
Here’s my situation: I had two big trips scheduled this year and I signed up for the CapOne Venture X card first. The $395 fee got eaten with $300 of travel credits for trip #1, plus a price match thing that kicked in and refunded me $100 and then free TSA-Pre and Premier lounges, etc… Anyway, the fee was absolved. Then the 79,000 miles kicked in and I booked the second trip (to WDW coming up in January) and it covered the flight, some of the hotel and a few straggling charges from the first trip.
I was happy in that I probably saved a grand after the bonus miles and the miles accumulated booking trip #1.
So now what? Do I cancel the card and look for new bonus points? Do I keep it through the January trip where I will accumulate a good amount of points, but nothing like the 79,000 sign-up bonus, obviously? I won’t be travelling THAT much next year after January, but there will be one trip to New England from CA in July.
What do the smart people do after they’ve burned through their sign-up bonuses?
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The answer in this game is almost always “it depends.” 
First: You always want to keep a credit card open at least until the 1 year anniversary hits, banks can and will claw back any sign up bonus if you close a card before that time. (There is actually a federal rule about changing credit card rules before a year is up that drives this.)
Quite often, cards are best used for the sign up bonuses (SUBs) and are mostly not great at the subsequent points earning. SUBS get the big bucks and the points earned via spend are sad at best.
There are exceptions to the rule (Chase Ink Cash, Freedom cards) - so I’d go through the benefits and see if a regular non-bonus year will still net you more than the cost of the annual fee.
For example, I opened a Marriott Boundless (SUB = 3 50K free night certificates) - after that the points are hardly worth earning since the Marriott points program is meh at best. BUT, I will get an annual 35K free night certificate by holding on to it - that will pretty easily offset the $95 annual fee, so there’s a good chance I’ll keep it just for that. (My alternative plan is to upgrade it to the much more expensive Ritz Carlton card in the future for better annual free night cert and airline lounge access etc, and close my Amex Plat. But that’s a unique situation for this card.)
When it comes to the Southwest cards I’m holding from earning my companion pass last year, I’ll probably let the annual points bonus hit this year on the personal card and cancel. I will likely keep the Performance Biz card open even with the higher fee on it: the annual bonus + 4 upgrades are nice to have, but the reimbursement for up to 365 WiFi credits adds a lot of value.
So, it’s all a balancing act.
Oh, last thing: you typically have up to 30 days after an annual fee hits to cancel and get the charge reversed.
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Churn and burn baby! You can keep the card open and accumulate some points on your upcoming trip, or look for that new signup bonus and double up by accumulating miles plus the bonus on the trip.
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I would like to get a Southwest card next. Does anyone know when Southwest has good perks for a sign up bonus?
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Are you looking to get a Companion Pass or just looking for points?
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Mainly this but companion pass wouldn’t be bad
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OK! In general, Companion Pass season starts in the fall and they tend to increase the sign up bonus on at least a few cards around October.
You have to earn enough points in a single calendar year to get a CP, so to maximize it, you want to earn all the points as soon after January starts as you can - then you have the CP for that year AND all of the following year.
(Edit: This paragraph added later:) People will get 1 card lateish October so their 3 month spend window rolls into the next year - BUT again: don’t spend enough to earn the points until the January statement. Then they get a 2nd card some time after October (I did it in December) to get that spend rolling. Best tactic is to get biz card first to make sure you are approved for that, then get personal card. (It’s not hard to get a biz card but is a little more of a hurdle and you might not want to bother with the personal if you can’t get the two cards to earn CP. DEFINITELY look up references online on the timing tactics, don’t want to make a mistake and earn points too early - there are always people in the points group who do.)
The US Credit Card guide has great charts on what the bonus has been in previous years, so you can look at the 4 SW cards and see which combo would work best for you. (I did both the personal Priority card and the Biz Performance to earn mine. Ended up with 165K points + the CP.)
BUT WAIT THERE’S MORE.
Right now they do have a super elevated bonus on the premier Biz card - and you could get CP with just the one card.
60k+60k offer: earn 60,000 Southwest Miles after spending $3,000 in the first 3 months, earn additional 60,000 Southwest Miles after spending $15,000 in total in the first 9 months. That’s 120k miles in total.
So, if hitting $15K in 9 months is reachable, that’s a terrific amount of points.
The Problem with this bonus structure however is Companion Pass timing: if you really wanted to get CP, you’d either have to:
- Hit the whole $15K spend before your December statement closed (and earn the CP the end of this year, so you’d only have it until the end of 2024) OR
- You’d have to hope this offer lasts until mid-October so you could apply then, be sure to hit the first $3K spend in the January statement, then reach the $15K spend whenever you could so all of your points arrive in 2024 like the usual CP tactic.
If the CP is a nice to have and the points are fine, then I think this is a pretty nice deal.
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This is super helpful- thank you! I started looking at the US cc website to see past offers and it look like fall/around New Years are the best offers on cards.
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It is scheduled to end 8/28
I actually do plan to use this offer. I already have ~70000 points from other people’s sign on bonuses. If I get the card that will get me 63000 to hit the spend. which means I only need to put 2K more on southwest cards. Should be easy with home improvement projects we have to do. However, I may save the last 2-3K for 2024 so I get another boost of 60000 at the start of the new year.
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Nice way to play it! 
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Wanted to add that since Cap1 has a no-fee Venture (One?) card, I’d wait until the $395 posts for year 2 and then call and ask to downgrade to the no-fee card, rather than cancel. Keep the credit history and the low credit usage %, and ditch the fee. You’ll be eligible for the Venture SUB at some point, or maybe already. I’d also ask if there’s any “offer to make keeping the Venture X more enticing” before you downgrade. I have no specific data points for Cap1 but some banks will give you a retention offer of X miles for Y spending, or X statement credit for Y spending to offset the annual fee.
What do you do with your brand new Venture One card? Put one recurring charge on it, something small and something that only happens 1-2 times per year. That way there’s activity on it and it’s actively reporting to the credit bureaus, but not taking away from the everyday spending you’re using to work towards a new SUB.
I just upgraded from Venture to Venture X last month, and they gave me the benefits right away but I’m still only paying my annual fee on the 12 month mark (8/31 for me) which means I got at least an extra month of benefits for free. I plan to keep it for now, with the $300/year travel credit it’s a better card for me than the $95/year Venture. My husband used my referral link for a Venture and we will likely downgrade him to Venture One when we hit 12.5 months for him.
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Just extended to 9/4. Hoping against hope for a little longer extension since timing this for 3 days (Dec 1-3) will be super tricky. Not that it’s not doable, just tricky.
If anyone’s interested in the rather advanced strategy to use this card to get Companion Pass for most of 2024 and all of 2025, this is a great primer.
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