Southwest Versus JetBlue for Flights to the Caribbean & Mexico

Emily and I are grateful to be nominated for best travel blog. We'd love your vote!
Ps: You can vote everyday!

Disclosure: We get a commission for links on the blog. You don’t have to use our links, but we’re very grateful when you do. American Express, Barclaycard, Chase, and US Bank are Million Mile Secrets advertising partners. Opinions expressed here are the author's alone, and have not been reviewed, approved or endorsed by our partners. Here’s our Advertiser Disclosure.

Many folks love to book award flights on Southwest and JetBlue to get to the Caribbean & Mexico.  Both airlines have no blackout dates and award flight prices are based on the cash cost of the flight, so when tickets go on sale, award flights are cheaper, too!.

Plus, both airlines have a great reputation for friendly service.

And it’s easy to earn points on both airlines with great credit card offers.  For example, you can earn a sign-up bonus of 50,000 Southwest points on the Chase Southwest Premier and Chase Southwest Plus after meeting minimum spending requirements.  Southwest is also a Chase Ultimate Rewards transfer partner.

Or earn 30,000 JetBlue points with the JetBlue Plus Card after completing minimum spending.

Southwest Versus JetBlue For Flights To The Caribbean Mexico

Southwest and JetBlue Fly Non-Stop to San Juan and Many Other Destinations in the Caribbean & Mexico. I’ll Compare Both Airlines’ Options for Award Flights

I’ll explain whether you’re better off collecting Southwest points or JetBlue points for flights to the Caribbean and Mexico.

Southwest and JetBlue Destinations in the Caribbean & Mexico

Link:   JetBlue Flight Routes

Link:   Southwest Route Map

Choosing between Southwest and JetBlue for non-stop flights to the Caribbean & Mexico will depend on your US departure city.

Southwest has non-stop flights to Caribbean & Mexico destinations departing from:

  • Atlanta
  • Austin
  • Baltimore
  • Chicago
  • Denver
  • Fort Lauderdale
  • Houston
  • Milwaukee
  • Orlando
  • Orange County, California
  • San Antonio

Starting in early 2017, Southwest will add non-stop routes to Mexico from Oakland, California.

You can fly Southwest to 9 destinations in the Caribbean & Mexico including:

  • Aruba
  • Belize City
  • Cabo San Lucas
  • Cancun
  • Montego Bay, Jamaica
  • Nassau, Bahamas
  • Puerto Vallarta
  • Punta Cana, Dominican Republic
  • San Juan, Puerto Rico
Southwest Versus JetBlue For Flights To The Caribbean Mexico

Fly Southwest to Beautiful Cabo San Lucas With Non-Stop Routes From Austin, Baltimore, Denver, Houston, and Orange County

JetBlue has 5 US departure cities to fly non-stop to Caribbean & Mexico destinations including:

  • Boston
  • Fort Lauderdale
  • New York (JFK)
  • Orlando
  • Washington, DC

JetBlue flies to the most Caribbean destinations of any airline, including:

  • Antigua
  • Aruba
  • Barbados
  • Bermuda
  • Cancun
  • Dominican Republic
    • La Romana
    • Puerto Plata
    • Punta Cana
    • Santiago
  • Grenada
  • Grand Cayman
  • Kingston, Jamaica
  • Montego Bay, Jamaica
  • Nassau, Bahamas
  • Port-au-Prince, Haiti
  • Puerto Rico
    • Aguadilla
    • Ponce
    • San Juan
  • Puerto Vallarta
  • St. Lucia
  • St. Maarten
  • Turks and Caicos
  • US Virgin Islands
    • St. Croix
    • St. Thomas
Southwest Versus JetBlue For Flights To The Caribbean Mexico

Experience Caribbean Culture in St. Lucia With JetBlue’s Non-Stop Flight Options From New York (JFK)

What About Cuba?

Starting in fall 2016, JetBlue will launch non-stop flights to Cuba from 3 US cities:

  • Fort Lauderdale
  • Orlando
  • New York (JFK)

And starting at the same time, Southwest will have non-stop flights from 2 US cities:

  • Fort Lauderdale
  • Tampa

These new flights can’t be booked, yet.  I’ll be sure to let you know when they’re available.

Southwest Versus JetBlue For Flights To The Caribbean Mexico

Soon, You’ll Be Able to Fly Non-Stop to Cuba on Southwest & JetBlue!

Before planning a trip to Cuba, check out Emily’s recent adventure!

Choose Southwest for Companion Pass & Free Bags

Here are some pros and cons of choosing Southwest for flights to the Caribbean & Mexico.


I love to fly Southwest because everyone gets 2 free checked bags.  Plus, they don’t charge change or cancellation fees.

And with the Southwest Companion Pass, a friend or family member can fly with you to the Caribbean or Mexico for almost free (just pay taxes and fees) on paid and award tickets for up to 2 years!  It can save you hundreds or thousands of dollars!  That’s why I think it’s the best deal in travel!

Southwest Versus JetBlue For Flights To The Caribbean Mexico

Take a Friend or Loved One With You to the Caribbean or Mexico for (Almost) Free With the Southwest Companion Pass

Southwest is a better choice for folks traveling to the Caribbean or Mexico from the South or the West Coast.  Because there are non-stop flights from cities in California and Texas.

In a moment, I’ll also tell you how it’s easier to earn Southwest points.  This means you’ll save money when you choose to book an award flight.


If you live in the Northeast, the only US departure city with non-stop flights to Caribbean & Mexico destinations is Baltimore.  Of course, you can depart from other US cities if you don’t mind a layover.

You won’t have much of a snack selection flying Southwest.  They typically only serve crackers, peanuts, and pretzels.

Southwest points expire if you don’t have any activity in your account in 24 months.

And if you’re booking a paid flight, Southwest flight routes will not show up on sites like Google FlightsOrbitz or Expedia.  You’ll have to search and book directly on Southwest.

JetBlue Is Great for Business Class, Extra Legroom, and In-Flight Entertainment

Let’s take a look at the pros and cons of flying JetBlue to the Caribbean & Mexico.


Folks love JetBlue because of things like free in-flight entertainment & Wi-Fi, more legroom, and snacks & drinks.  Keep in mind the Wi-Fi coverage area is limited to the US, so you might lose signal during a flight to or from the Caribbean or Mexico.

JetBlue offers Mint Business Class seats on certain flights from New York and Boston to 5 Caribbean destinations including:

  • Aruba
  • Barbados
  • Grenada (seasonal)
  • St. Lucia
  • St. Maarten

In Mint Business Class, you can enjoy early boarding, excellent in-flight dining options, expedited check-in, lie-flat seats, and more.

Southwest Versus JetBlue For Flights To The Caribbean Mexico

Enjoy a Lie-Flat Bed and Great Service When You Fly JetBlue’s Mint Business Class to Certain Caribbean Destinations


Even if you’re flying coach on JetBlue, you’ll still have more legroom than on a Southwest flight.

I also like that you can pool JetBlue points with friends and family members to earn award flights faster.

And folks with JetBlue Mosaic status have extra perks on JetBlue flights like:

  • 2 free checked bags
  • Complimentary alcohol on flights
  • Expedited security clearance
  • No charges for flight cancellations or changes

Lastly, JetBlue points never expire!


Depending on the fare type your purchase, it could cost $150 to change or cancel your flight if you don’t have elite status with JetBlue.  And you could pay $20 or more to check a bag if you purchase the cheapest JetBlue airfare.

I’ve written before about how you can avoid JetBlue baggage fees.  And folks with the JetBlue Plus or JetBlue Business can also get a free 1st checked bag for themselves and up to 3 companions on the same reservation when you use your card to pay for your ticket.

All non-stop JetBlue flights to the Caribbean & Mexico depart from cities on the East Coast.  If you’re departing from any other US city, you’ll have to stop in 1 of the 5 departure cities I listed earlier.

Other Ways to Get to the Caribbean & Mexico

Link:   How to Fly to the Caribbean With British Airways Avios Points  

Link:   Why Chase Ultimate Rewards Points Are Terrific for Flights to the Caribbean

Southwest & JetBlue are terrific options for getting to the Caribbean & Mexico using points.  But, you also have other options.

You can use British Airways Avios points to fly American Airlines and Alaska Airlines routes to the Caribbean & Mexico.

Or, you can transfer Chase Ultimate Rewards points to Flying Blue or United Airlines to book award flights.

Earn Southwest & JetBlue Points

Link:   Chase Southwest Premier (Personal)   

Link:   Chase Southwest Premier (Small Business)

Link:   Chase Southwest Plus 

Link:   JetBlue Plus Card From Barclaycard

Link:   JetBlue Business Card From Barclaycard 

All 3 Chase Southwest cards are currently offering 50,000 point sign-up bonuses after meeting minimum spending requirements.  This makes it a great time to earn the Companion Pass!  With the 3 Southwest cards you’ll also earn:

  • 6,000 Southwest points each year on your account anniversary with the Chase Southwest Premier (personal and small business)
  • 3,000 Southwest points each year on your account anniversary with the Chase Southwest Plus
  • 2 Southwest points per $1 you spend on Southwest purchases

Keep in mind Chase has tightened their card application rules.  They’ll likely deny your application if you’ve opened ~5 or more credit cards with any bank (excluding certain business cards) in the past 24 months.

You can also transfer Chase Ultimate Rewards points to Southwest if you have a card like the Chase Sapphire Preferred or Chase Ink Plus.  This makes it even easier to book award flights!

Jump-starting Your JetBlue Points Balance

Meanwhile, JetBlue has 3 cards that are issued by Barclaycard.

The JetBlue Plus and JetBlue Business card have a 30,000 point sign-up bonus after meeting minimum spending requirements.  You’ll also get:

  • 5,000 JetBlue points (worth ~$70 in JetBlue flights) each year on your account anniversary
  • 6 JetBlue points per $1 you spend on JetBlue purchases
  • Free 1st checked bag for cardholder and up to 3 companions on the same reservation when you use your card to pay for your ticket

The JetBlue Card has a 5,000 point sign-up bonus after meeting minimum spending requirements.  You do NOT get a free checked bag with this card.  You’ll earn 3 JetBlue points per $1 you spend on JetBlue purchases.

Remember, many small business cards will NOT appear on your personal credit report.  So, if you apply for the JetBlue Business card, it will not count toward Chase’s 5 card limit!

And don’t forget, you don’t need a large corporation to get a small business card.  There are many ways to qualify for a small business card.  As long as you’re looking to make a profit with your growing small business, it’s worth applying.

Bottom Line

You have many options for flights on JetBlue and Southwest to the Caribbean & Mexico.

Folks on the East Coast might prefer JetBlue because there are more non-stop flight options.  JetBlue is also appealing because of the extra legroom, Mint Business Class offering, and points that don’t expire.

Southwest has non-stop options to the Caribbean & Mexico from 9 US cities.  And Southwest is a much better option for folks with the Companion Pass.  Because a friend or loved one can fly with you for almost free, which can save you hundreds of dollars each trip!

With the current airline credit card offers, you can earn sign-up bonuses and other perks like anniversary points to use towards JetBlue and Southwest award flights to the Caribbean & Mexico.

Which airline do you prefer flying to the Caribbean or Mexico?

* If you liked this post, why don’t you join the 25,000+ readers who have signed-up to receive free blog posts via email (only 1 email per day!) or in an RSS reader …because then you’ll never miss another update!

Editorial Disclaimer: Neither the responses below nor the editorial content on this page are provided or commissioned by the bank advertisers, and have not been reviewed, approved or otherwise endorsed by the bank advertisers. Opinions expressed here are the author’s alone, not those of the bank advertisers. It is not the bank advertisers’ responsibility to ensure all posts and/or questions are answered.

Leave a Reply

Your email address will not be published. Required fields are marked *

3 responses to “Southwest Versus JetBlue for Flights to the Caribbean & Mexico

  1. I’m booking a trip to Jamaica on Southwest. I was surprised to see the “almost free” cost to bring my companion is $140! The majority of that is taxes and fees levied by Jamaica or the Montego Bay airport. Still, better than paying full price.

  2. Southwest options to the Caribbean are very limited from FLL. They currently only go to the Bahamas and Puerto Rico. The best thing about their flights is the no fees for cancelation. Weather in the Caribbean can be very fickle and it’s not fun to be stuck on a small island in bad weather. It’s nice to be able to wait until the last minute before deciding to cancel without paying a fee.

  3. Southwest airline deals are simply superb ( of course cheap) even when it comes to travelling with in the States. One good thing behind this may be their transFAREncy policy as far as their airfares are concerned. That makes the travelers choose Southwest again and again.