How many awesome trips can you and a companion squeeze in before your Southwest Companion Pass runs out? That’s the challenge for travelers who receive the coveted Companion Pass, which is essentially a buy-one-get-one deal on your Southwest flight.

As long as you pay cash or redeem Southwest Rapid Rewards points for a flight for yourself, you can bring a companion for free, aside from the cost of taxes and fees, which is typically only about $5 each way.

With a Companion Pass, there’s no limit on the number of trips you and a guest can take. You aren’t even committed to the same person all year round, as Southwest lets you change your designated buddy up to three times each calendar year.

So where can the two of you fly together to maximize your Companion Pass? Here are some of the best places that Southwest flies to visit.

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BROWSE CARDS

Best vacation spots with Southwest Airlines for you and your companion

Traveling companions are clamoring for tickets to these popular destinations.

1. Hawaii for New Year's

Southwest began operating flights to the Aloha State from the West Coast in 2019, and since then, Southwest flights to Hawaii have only increased. Whether you’re a snowbird seeking Hawaii’s seemingly eternal summer, or the kids are out of school for a few weeks during winter break, Hawaii makes an ideal place to begin a new year.

Southwest operates flights both from the mainland U.S. and between islands, so you might end up using your Companion Pass a few times during a Hawaiian holiday if you’re planning to hop between the state's diverse islands.

Happily, Southwest flies to Hawaii year-round.

2. New Orleans for Mardi Gras

Dixieland jazz, world-famous cuisine and a laid-back culture found nowhere else in the world — New Orleans belongs on every traveler’s wish list. Unsurprisingly, prices can spike during Mardi Gras, which is when most tourists want to visit the city.

With a Companion Pass, effectively 50% off your combined fares, you'll get a significant discount.

3. Cancun, Mexico, for spring break

Forget the spring break stories: Cancun has something to offer every traveler. Along with its white-sand beaches, crystal-blue waters and world-famous margaritas, Cancun is your launch pad for exploring ancient Mayan ruins in Chichen Itza and diving into the waters of beautiful underground sinkholes called cenotes.

4. Aruba in August

Southwest flights to the Caribbean include trips to the Bahamas, Puerto Rico and more.

One of the best spots, the ABC islands — Aruba, Bonaire and Curacao — lie outside the part of the Caribbean prone to hurricanes, making this sunny region an excellent late-summer getaway.

5. Las Vegas for Labor Day

If you and your companion are looking for one last summer hurrah, Las Vegas is the place. Here you’ll find the perfect water wonderland, regardless of whether you like the serene pools or the parties (or both).

Even if you think you’re a Vegas pro, the city has changed fairly significantly over the past year. Many new Las Vegas hotels have opened recently, including the first new hotel on the Strip in more than a decade.

6. Orlando, Florida, during winter break

(Photo courtesy of Walt Disney World)

The periods when kids are out of school can make for a bad time to fly to Orlando, which is home to Walt Disney World, Universal Orlando Resort and tons of other family-friendly destinations that can have massive crowds.

But if you’re traveling to a kid-friendly place, there’s a good chance you’re going with kids. And if you’re going with kids, you’ll likely need to go during a school break. If that’s the case, skip summer (when it can be hot and humid) and go during winter break.

Depending on where you’re coming from, you’ll escape snow and instead arrive in the cool (yet still likely warmer and sunny) Florida. Plus, winter can be especially festive in Florida as the theme parks usually add extra decorations for the holidays.

Even if you’re not into cartoon characters and thrill rides, lounging by the pool at any of the many resorts is a prime way to enjoy the Florida sun. If you must fly to Orlando at peak season, at least your Companion Pass will help keep costs down.