How to Get Big Travel on Southwest With the Chase Sapphire Preferred Bonus

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Sign-up for 1 credit card and get up to ~$715 worth of award flights on Southwest for a beach vacation in Cancun, a getaway in New York, or a weekend in New Orleans! 

And you can double that to ~$1,430 that if you have the Southwest Companion Pass!

When you sign-up for the Chase Sapphire Preferred you’ll earn 50,000 Chase Ultimate Rewards points after meeting the minimum spending requirements.  And you can transfer those points directly to Southwest at a 1:1 ratio.

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Visit 1 of Southwest’s International Destinations, Like Punta Cana or Cancun! I’ll Show You Lots of Options!

I’ll give you some ideas on how to use your Southwest points for Big Travel with Small Money!

About the Chase Sapphire Preferred

Link:  Chase Sapphire Preferred

With the Chase Sapphire Preferred card, you’ll earn 50,000 Chase Ultimate Rewards points when you spend $4,000 on purchases within the 1st 3 months of opening your account.

This is the best bonus ever on the card, and it’s the #1 card I recommend for beginners to miles and points.

And Chase Ultimate Rewards is my favorite points program.  Because the points are flexible, they transfer 1:1 to airline and hotel partners like Southwest and Hyatt.

Be sure to read my review of the card!

Why Southwest?

It’s no secret Emily and I love to fly Southwest domestically.  That’s because everyone gets:

  • 2 free checked bags on every flight
  • No change or cancellation fees
  • No blackout dates on award flights

And if you have the Southwest Companion Pass, you can fly with a partner for nearly free!  In fact, I call it the BEST deal in domestic travel!

For long-haul international flights, we transfer our Chase Ultimate Rewards points to partners like United Airlines, or Singapore Airlines to fly in Business or First Class.  But for flights within the US, we LUV Southwest! 🙂

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Coast to Coast, Southwest Flies All Over! They Fly to International Destinations, Too!

And, Southwest has started to fly internationally!  You can get a great deal to popular destinations like Cabo San Lucas or Mexico City.

The 50,000 Chase Ultimate Rewards points sign-up bonus on the Chase Sapphire Preferred is worth ~$625 to ~$715 in Southwest flights.  And almost double that if you have the Southwest Companion Pass!

That’s because when you transfer Chase Ultimate Rewards points to Southwest, each point is worth between ~1.25 and ~1.43 cents, in Southwest airfare, depending on the route and the date.  And because the number of points you pay is tied to the price of the ticket, when Southwest has a sale, you’ll pay fewer points for an award seat!

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Your Points Are Worth More Than Cash Back When You Transfer Them to Southwest

This is a better rate than redeeming for cash back (where points are worth 1 cent each).  You can also book flights through the Chase Travel Portal, where points are worth 1.25 cents each.

But remember, if you have the Southwest Companion Pass, a friend or family member can fly with you for nearly free, even on award flights.  In that case, it’s worth transferring them to Southwest instead.

Folks in these 10 cities should especially consider going for the Southwest Companion Pass!

Where Can You Go?

Let’s look at some fun trip ideas using your Southwest points!

1.   Northern California Area

Southwest flies to these cities in or near Northern California:

  • Oakland
  • Reno
  • Sacramento
  • San Francisco
  • San Jose
How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Red Or White? Try Wines at Vineyards in Northern California, Visit San Francisco, or Go Skiing in the Sierra Nevada Mountains!

This part of the US has so much to do!  You could:

  • Visit San Francisco
  • Tour the wineries in Napa Valley
  • Golf or ski in the Sierra Nevada mountains
  • Drive the scenic Pacific Coast Highway
  • Relax on Lake Tahoe
How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Hug a Tree – a Really Big Tree! Visit Redwood National Park to Experience These Beautiful Forests

You could visit Redwood National Park to see some of the biggest trees in the world!

I found round-trip non-stop award flights over Valentine’s Day from Dallas to Sacramento for only 18,000 Southwest points and ~$11.  That’s much less than the 25,000 miles or points most domestic airlines charge.  And there are no blackout dates to think about!

If you decide to visit vineyards, be sure to take your Chase Sapphire Preferred card with you.

Because it’s a Visa Signature card, you can enjoy 2 complimentary tastings per cardholder and discounts on wine purchased in person at over 60 wineries in Napa and Sonoma County.  The terms say this benefit expires at the end of 2015, but here’s hoping they decide to renew it for another year!

2.   Fun in the Sun

Southwest also serves lots of beach destinations, including:

  • Cancun
  • Fort Myers
  • Nassau, Bahamas
  • Punta Cana, Dominican Republic
  • San Juan, Puerto Rico
  • San Diego
  • West Palm Beach
How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Explore Underwater Caverns Under the Sea in Cancun! And Enjoy the Sun When You Get Back up to Dry Land!

I wrote about how to fly to the Caribbean using Chase Ultimate Rewards points, including on Southwest.

In some cases, it’s fewer points to book an award ticket with Southwest, especially when there’s a flight sale!  Always run the numbers before you book to make sure you’re getting the best deal.

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Folks in Chicago Can Swap Their Snow Boots for Flip Flops This Winter! I Found Award Tickets for Under 6,000 Southwest Points 1-Way to Montego Bay, Jamaica, Where Temperatures Are in the Mid-80s Year Round!

For example, I checked award flights to see how much folks in Chicago would have to pay for a mid-winter warm-up to Montego Bay, Jamaica, and found seats for only 5,740 Southwest points + $50 1-way.  That’s an incredible deal, and far below what you’d pay with nearly any other airline!

There are plenty of other beaches to explore!

You can fly direct to Cancun from:

  • Atlanta
  • Austin
  • Baltimore
  • Chicago
  • Denver
  • Milwaukee
  • San Antonio

And you can fly non-stop to Punta Cana from:

  • Atlanta
  • Baltimore
  • Chicago
  • Milwaukee

Lots of Southwest’s beach destinations are international flights, so be sure to pack your passport.

3.   New York City

Visit the Big Apple!  Southwest flies to New York’s LaGuardia and Newark airports.

And Southwest points are another great way to get Big Travel with Small Money when traveling to New York.

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Hang Out in Central Park While Exploring New York!

Folks often think getting to New York is expensive, but it doesn’t have to be!

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Wanna Get Away? Flights Between New York and Phoenix Are Only ~7,000 Southwest Points in April 2016!

I found lots of dates with award seats for around 7,000 Southwest points from Phoenix to New York!

And on the flip side, New Yorkers can enjoy some Arizona sun for the same amount!  Win-win!

4.   New Orleans

For those of y’all who have never been to New Orleans, you’re missing out on the fun!  There’s so much to do there for young folks, families, and everyone else!

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Catch Some Beads! I Found Award Flights to New Orleans During Mardi Gras for Under ~6,000 Southwest Points Each Way From Washington, DC

Use Southwest points for amazing experiences, like New Orleans during Mardi Gras.  I found award flights from Washington, DC, for ~5,500 Southwest points each way.  You can watch the parades, catch beads, and try the Hurricane – a New Orleans specialty cocktail!

5.   And Beyond!

Link:   Southwest Route Map

Southwest flies to dozens of US (and international!) destinations.  So be sure to check out their route map to see where you want to visit!

A few other places I found interesting include:

How To Get Big Travel On Southwest With The Chase Sapphire Preferred Bonus
Baby’s 1st Hike! Make Unforgettable Memories in the Great Outdoors, Like Glacier National Park in Montana

And remember, Southwest points are very flexible and there are NO blackout dates to worry about.  If there’s a seat for sale, you can book it with Southwest points.

Bottom Line

There are lots of amazing places you can visit with your Southwest points after you transfer your Chase Ultimate Rewards points.

You’ll earn 50,000 Chase Ultimate Rewards points when you sign-up for the Chase Sapphire Preferred card and meet the minimum spending requirements.  That’s enough for up to ~$715 worth of Southwest flights!

Have a look at the Southwest route map, and always do the math to make sure get a good deal.

The rest is up to you!  Where would you go with 50,000 Southwest points?

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! :)

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