Getting your Companion Pass soon? Check out these amazing Southwest international destinations for travel inspiration
Signing up for credit cards through partner links earns us a commission. Terms apply to the offers listed on this page. Here’s our full advertising policy: How we make money.
Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers.
If you’re not a frequent Southwest Airlines flyer, you might not know that they fly to a bunch of fun international destinations, along with extensive routes within the U.S., including Hawaii. If you’ve got the Companion Pass, that makes the following routes even more exciting.
the Southwest Companion Pass is the best deal in travel. With it, you can bring a travel buddy with you — every single time you fly Southwest — for just the cost of taxes and fees. That could save you thousands, depending on how often you fly, and it effectively doubles your Southwest points value. To earn the Companion Pass, you must earn 125,000 qualifying Southwest points in a calendar year. Fantastically, Southwest credit card welcome bonuses count toward that requirement! So you can apply for a couple Southwest cards and practically earn the Companion Pass straightaway:
[table id=572 responsive=scroll responsive_breakpoint=phone /]
This makes the Southwest cards some of the best airline credit cards available. Just note that you can only hold one Southwest personal card at a time, so you’ll need to open one personal and one small business card. Also read this post on the Chase 5/24 rule before applying.
Once you earn the Companion Pass, you’ll probably be itching to make the most of it by adding a friend or family member to fly with you (on paid and award flights) for just the cost of taxes and fees. Here are a few international Southwest destinations you might consider for a quick getaway using your newly-minted Southwest Companion Pass.
Southwest international destinations
You can see where you can fly on Southwest by checking out their interactive route map. It’s easy to use by just clicking on your home airport, and you can even filter by non-stop flights if that’s what you prefer.
Here are the destinations on my top four list.
Southwest flies to two cities in Costa Rica: San Jose (non-stop from Houston and Baltimore), and Liberia (non-stop from Houston, Baltimore, and Fort Lauderdale). But you can connect from dozens of other cities. Costa Rica is well-loved for its eco-tourism, volcanoes, and beaches. Friends of mine visited earlier this year with their kids and had an absolute blast zip-lining though the jungle and hanging out on the beach at a rustic hotel near Liberia.
Once you’re in Costa Rica, you can save more money by booking a hotel with points. Folks rave about the Andaz Costa Rica Resort at Peninsula Papagayo, which as a Hyatt category 5 hotel costs only 20,000 Hyatt points per night. It’s simple to transfer Chase Ultimate Rewards points to Hyatt from cards like the Chase Sapphire Preferred® Card, Ink Business Preferred Credit Card or Chase Sapphire Reserve®, all of which rank among the best credit cards for travel on the market.
Folks looking for a relaxing beach getaway can fly Southwest to Montego Bay, Jamaica non-stop from six cities – Chicago (Midway), St. Louis, Baltimore, Orlando, Fort Lauderdale, and Houston (or connect from just about any other Southwest city in the U.S.).
The kids and I have never visited, but we’re considering a quick trip there to escape the winter cold in the Northeast. If we go, a must-see is Dunn’s River Falls for swimming and enjoying the scenic tiered waterfall there.
I’ve got my eye on staying at the all-inclusive Hilton Rose Hall Resort & Spa in Montego Bay for a truly stress-free getaway. And because I have Hilton elite status (which you can get automatically from cards like the Hilton Honors American Express Surpass® Card, The Hilton Honors American Express Business Card and Hilton Honors Aspire Card from American Express), we’ll get our fifth night free on award stays. The information for the Hilton Aspire card and Hilton Surpass card has been collected independently by Million Mile Secrets. The card details on this page have not been reviewed or provided by the card issuer.
Grand Cayman Island
If you’re a fan of snorkeling, diving or just enjoying swimming at the beach, Grand Cayman is a terrific pick. You can fly Southwest non-stop from Baltimore, Fort Lauderdale, and Houston, or connect from tons of other U.S. cities. Kids and grownups alike will love checking out Stingray City, where you can get up close and personal with humongous stingrays.
One of the top rated resorts in Grand Cayman (in fact, in all of the Caribbean) is the Kimpton Seafire Resort and Spa, where paid rates can be in excess of $1,000 per night. But you don’t have to pay top dollar for a luxury stay here, because you can redeem points from cards like the IHG® Rewards Club Premier Credit Card instead.
Southwest flies to Belize City from Denver, Houston, and Fort Lauderdale (with connection options from other U.S. cities) – and it’s an incredible destination for any travel style. Whether you’re into ecotourism, historic sites or just flaking out on a beautiful beach, you can take your pick in Belize.
Meghan attended a friend’s wedding in Ambergris Caye, Belize, and has great things to say about it. She says it’s an ideal spot for divers, and enjoyed other fun activities like paddleboarding and ziplining while there.
There aren’t as many big chain hotel options in Belize compared to other destinations, but that doesn’t mean you can’t redeem points for a free stay here. For example, you can book boutique and independent hotels with miles earned from the Capital One Venture Rewards Credit Card at a rate of 1 cent per Capital One mile. You can read our full Capital One rewards review to see how unbelievably easy it is to receive free travel from those miles.
If you’ve got a stockpile of Southwest or the Southwest Companion Pass (or both!), you don’t have to limit your adventures to within the U.S. Southwest is certainly known for its domestic routes, but you can use Southwest points to fly to a number of awesome international destinations in the Caribbean, Mexico, and Central America – all perfect for a relaxing vacation or quick getaway. My family is hoping to sneak off to a couple of these spots this year – and because with the Companion Pass, one of my kids will fly for just the cost of taxes and fees, we’ll do so at a huge savings.
Plus, if you collect points from the best hotel credit cards, you can stay for free as well – even if it’s not a chain hotel.
Which Southwest destinations are inspiring you to travel more this year? Let me know in the comments. And subscribe to our newsletter for more inspiration for using your miles and points.
Chase Sapphire Preferred® CardAPPLY NOW
Chase Sapphire Preferred® Card
Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That’s $750 when you redeem through Chase Ultimate Rewards®.
Enjoy benefits such as a $50 annual Ultimate Rewards Hotel Credit, 5x on travel purchased through Chase Ultimate Rewards®, 3x on dining and 2x on all other travel purchases, plus more.
Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards®. For example, 60,000 points are worth $750 toward travel.
With Pay Yourself Back℠, your points are worth 25% more during the current offer when you redeem them for statement credits against existing purchases in select, rotating categories
Count on Trip Cancellation/Interruption Insurance, Auto Rental Collision Damage Waiver, Lost Luggage Insurance and more.
Get complimentary access to DashPass which unlocks $0 delivery fees and lower service fees for a minimum of one year when you activate by December 31, 2024.
16.74% – 23.74% Variable
Either $5 or 5% of the amount of each transfer, whichever is greater.
Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)