[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).
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.
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- Link: Dallas to Cabo fare Calendar
- Link: Dallas to San Jose, Costa Rica fare Calendar
- Link: Dallas to Turks & Caicos fare Calendar
- Link: Use the Southwest gift card discount at Sam’s club to save $50 on Southwest flights
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: Rent a car for cheaper by using Priceline’s “Express Deals”. The rental car company will be hidden until after you purchase, but this allows those companies to undercut the published rate indirectly. You can remove low quality companies from those hidden results. The trick is to use the quality filter on their website to remove any rental car company with a review rating under 7.0 and then pick the deals that survive the filter.
- 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: Vacation rentals on Vrbo are usually cheaper per night for longer stays than shorter stays. This is due to three main factors; The first is that most properties have a cleaning fee that is a fixed rate, the second is that many hosts provide discounts for stays longer than 6-days, the third is that the Vrbo service fee percentage is higher on short stays.
- Tips: You can (and should) sort the Vrbo vacation rental search results by “Total” price. Doing so exposes properties with high fees. For example, a $140 per-night property with $100 fees will rank as being more expensive than a $150 per-night property with $30 fees, when sorted. Sorting by “most reviews” is also a good option, as this will show you the most popular properties.
- 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.
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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.
Note: OTAs such as Travelocity and Priceline allow free cancellation without penalty within 24-hours after you purchase. As deals sell-out or expire quickly, this policy will allow you to “lock-in” the cheap fare while you sort out a plan. Just keep in mind that after 24-hours you will not be able to cancel without the regular penalty.
- Book this fare on: Priceline, BookingBuddy, Travelocity, Tripadvisor, Skyscanner, Expedia, Orbitz, Hotwire, CheapTickets, Kayak.
- Link to CheapTickets.com coupon code page – Check this page on Cheaptickets.com to save about 10% to 20% on your next Hotel or Package booking.
- Link to Travelocity coupon code page – Check this page on Travelocity to save about 10% to 20% on your next Hotel or Package booking.
- Link to Orbitz coupon code page – Check this page on Orbitz to save about 10% to 20% on your next Hotel or Package booking.
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- Airfare + hotel: Priceline, Travelocity, Orbitz, CheapTickets.com, Expedia, Hotwire, Skyscanner, Kayak
- Vacation rentals: Vrbo
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