Image Credits: Karen Blaha, Creative Commons 2.0 (flickr)
Published June 6, 2022 by

Cheap Flights: Dallas to/from San Jose del Cabo, San Jose Costa Rica, Providenciales, Turks & Caicos Islands $233-$291 r/t [August-November] – Southwest

[06/06/2022 @ 10:32 PM CT] Book this fare on: Southwest, Sam’s Club Southwest gift card.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

This website contains cookies and links to companies that may compensate this site when you click on their links or ads. To view our ad disclosure and privacy policy, visit this page (link).

Southwest has round-trip flights from Dallas (DAL) to San Jose del Cabo, San Jose Costa Rica, Providenciales, Turks & Caicos Islands (SJD, SJO, PLS) for $233-$291, with a connection. About $96-$164 each-way. Flights September to November. No Fridays. Origin/Destination reversible.

Note: Turks & Caicos has limited availability, mid-August to the end of August.

Carry-on and checked bag are allowed for free. Southwest doesn’t charge change fees.

Additional Savings: Sam’s Club is selling $500 Southwest gift cards for $449 [linked]. You can save an additional $50 on Southwest flights if you travel often enough or with a big enough group to burn through the gift card credit.

Use the fare calendar links to pull up the fares.

Flights on Southwest are often matched by other airlines, before committing to a purchase, do a check on BookingBuddy, Kayak, or Skyscanner to see if any other airline is offering a better deal.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn’t be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 9-month moving average.

We don’t charge a subscription fee. All our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

When you are ready to book your flight or hotel, please use the links on our page to begin your booking process so we receive credit for the referral.

  • Tips: The Chase Sapphire Preferred® Card allows for 1-to-1 point transfers to several airline loyalty programs. Booking with points is a good alternative to paying with cash when the price of airfare is high. Here is the current list of Chase Sapphire transfer partners: United, Southwest, jetBlue, British Airways, Iberia, Singapore Airlines, Emirates, Air France, KLM, Virgin Atlantic, Aer Lingus, and Air Canada.
  • Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
  • Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.

I was able to pull this up on Southwest. Screenshot taken when this post was initially created. See timestamps at the top of this post.

Flight Details:


Our Affiliate Links:

This site receives referral credit when you use links on our page to open our affiliate’s page. By using our affiliate links when you begin your airfare or hotel search, you are supporting this site. Thanks.

Flights departing from a different city (our other websites):

Other Useful Links:

  • [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the flight deal posts)

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

    Airfare Deals Southwest