How to Fly (Including Business Class!) to the Caribbean With Chase Sapphire Preferred

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If you have the Chase Sapphire Preferred card, you can transfer your Chase Ultimate Rewards points to airline partners, including United Airlines, for award flights to the Caribbean, even in Business Class!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Enjoy an Award Flight to the Caribbean With Your Chase Ultimate Rewards Points!

I’ll show you how to use your points for award flights, how to earn more points on everyday purchases, and where to stay in the Caribbean!

How To Fly With Chase Sapphire Preferred Series Index

What Are Chase Ultimate Rewards Points?

Link:   Chase Ultimate Rewards Transfer Partners

Chase Ultimate Rewards points are flexible points you can transfer at a 1:1 ratio to certain airlines and hotels.  There are never any transfer fees and most transfers are instant.

I also like that Chase Ultimate Rewards points do NOT expire.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Chase Ultimate Rewards Points Transfer 1:1 to British Airways, Southwest, and United Airlines. These Are the Best Partners to Use for Award Flights to the Caribbean

You’ll usually get much better value from your points from transferring to airline and hotel partners than if you redeem them for travel bookings, merchandise, or cash back.

There are a number of ways to visit Caribbean, but we’ll focus on these 3 Chase airline partners:

  • British Airways
  • Southwest
  • United Airlines

Use United Airlines Miles for Caribbean Flights

Your best choice for transferring airline miles from Chase Ultimate Rewards depends on your home airport, and where you want to visit.

I’ll focus on United Airlines miles, because anyone in the mainland US, Canada, or Alaska can visit the Caribbean for a set number of miles!  But I’ll show you when British Airways Avios points may be better for you.  And when Southwest makes sense.

Note:   Once you transfer your Chase Ultimate rewards points to a travel partner, you can NOT transfer them back.  And they become subject to the airline or hotel’s expiration rules.

Are There Other Options?

Link:   British Airways Award Flight Calculator

Link:   Wandering Aramean’s Avios Map

If you have the Southwest Companion Pass, or find a cheap ticket on Southwest, Southwest points are usually a better option.

Folks who live in cities close to the Caribbean, like Miami or Orlando, or near the East Coast, might prefer to use British Airways Avios points because it may cheaper than flying with United Airlines miles.

You can use British Airways Avios points for award flights on American Airlines routes.

For example, you can fly non-stop from Philadelphia to Nassau, Bahamas, for 15,000 British Airways Avios points round-trip in coach according to Wandering Aramean’s Avios calculator tool.  So if you can find award seats with British Airways, it’s much fewer points than on United Airlines.

Be aware that starting February 2, 2016, you’ll pay 7,500 British Airways Avios points for short-haul flights.  And remember British Airways charges per flight segment.  So if you have to connect, you’ll pay more points for the connecting flights.

American Airlines has a few routes to the Bahamas, so it’s always worth checking.  And remember you can fly 1-way using British Airways Avios points.  And the other direction with United Airlines miles!

Using United Airlines Miles to the Caribbean

Link:   United Airlines Award Chart

Link:   United Airlines Partners

Link:   United Airlines Partner Award Chart

Link:   The Ultimate Guide to United Airlines Miles

I’ve written about how to use United Airlines miles to visit the Caribbean.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

United Airlines Has Reasonable Rates to the Caribbean Islands

United Airlines charges:

  • 35,000 United Airlines miles for a round-trip coach award ticket
  • 60,000 United Airlines miles for a round-trip Business Class award ticket
  • 80,000 United Airlines miles for a round-trip First Class award ticket

Note that United Airlines doesn’t have many planes that have First Class to the Caribbean.  So your options are mainly coach or Business Class.

You can use United Airlines miles to fly on:

  • Air Canada
  • Copa Airlines
  • United Airlines

You do NOT have to memorize which airlines fly to the places you want to visit.  They’ll show up automatically in the award search!

You might decide to fly on a partner airline if:

  • Their flight times are more convenient for you
  • There’s nothing available on United Airlines
  • You prefer to fly out of a certain airport (JFK instead of EWR, for example)
  • You want to try a new airline

And keep in mind, you can use United Airlines miles to book award flights on partner airlines, but you can NOT transfer them to the other airline directly.

Let’s look at specific examples.

1.   From New York

a.   Punta Cana, Dominican Republic

Folks in the Big Apple who want to visit Punta Cana have lots of flight options.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Award Seats Are Available Every Day in February and March 2016!

There’s an award seat available every single day in February and March 2016.  Perfect for a mid-winter vacation!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Choose From 2 Direct Flights, and Be in Punta Cana in ~4 Hours!

United Airlines even has award seats in both coach and Business Class on 2 non-stop flights from Newark.

Or you can choose a different New York-area airport like LaGuardia or JFK if you don’t mind connecting, or if you want to fly another airline.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

If You Have the Option Between a Saver or Standard Award, Always Pick the Saver Level! It’s the Same Set of Flights, but Costs Much Fewer Miles!

And, if you have the choice between a “Saver” award or a “Standard” award for the same class of service, always choose the Saver level.  In this example, you’ll pay over double the miles for the same flights if you select “Standard”!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

If Your United Airlines Award Shows Mixed Cabins, Be Sure to Find Out What Class of Service You’ll Get for Each Flight!

Note that United Airlines sometimes mixes their cabins.  In this example, the shorter flight from JFK to Toronto, Canada, is in coach, but the flight from Toronto, Canada, to Punta Cana is in Business Class.  But always check by clicking “Details.

b.   Montego Bay, Jamaica

I found 8 flights from New York to Montego Bay on the date I searched.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Fly Directly to Jamaica from New York in Just 4 Hours!

On many days, there’s a non-stop morning flight available in coach or Business Class.  Be on the beach in Jamaica by the afternoon!

There aren’t as many flights to choose from, so this route may require more flexibility.  But you’ll have ~10 options each day, so you can still find a seat.

c.   Nassau, Bahamas

The Bahamas are only ~3 hours by plane, and there are ~40 flights to choose from each day!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Snag a Non-Stop Flight to The Bahamas for 35,000 United Miles Round-Trip in Coach!

There are plenty of award seats available nearly every day this winter and spring, including over Valentine’s Day!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Plan a Romantic Getaway With Your United Airlines Miles!

This is a quick and convenient route, even for a weekend getaway!

2.   From Chicago

a.   Punta Cana, Dominican Republic

Folks in Chicago might need a break from their winter at some point!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

I Found Non-Stop Flights on the Dates I Searched!

And they’re in luck!  There are plenty of coach and Business Class award seats to Punta Cana, on United Airlines, Air Canada, and Copa Airlines.

You’ll need to be more flexible if you want the non-stop seats.  On the dates I searched, I easily found round-trip flights for 35,000 United Airlines miles plus ~$106 for taxes and fees.

b.   Montego Bay, Jamaica

Finding an award seat to Montego Bay is more difficult, but it can be done if you don’t have fixed dates.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Award Seats to Montego Bay Are Patchy and Have Connections

I was able to find an award seat on United Airlines, but nothing that was non-stop.  And most of the connecting flights make the total trip 15 hours or more!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

I Found a Seat With a Short Layover After Searching Around

After some searching, I found flights with an hour-long connection in Washington, DC.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

For This Route, Southwest Is Cheaper!

For this particular route, I found similar flights on Southwest for ~14,000 Southwest points plus ~$122.  That’s much cheaper than the 35,000 United Airlines miles you’d pay!

But, you can still use your Chase Ultimate Rewards points because they transfer to Southwest at a 1:1 ratio!

Routes like this are a good reminder to always run the numbers before you book!

c.   Nassau, Bahamas

Award seats from Chicago to The Bahamas are also sparse, especially for the non-stop route.  But if you’re flexible, you can find them!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

There Aren’t a Lot of Non-Stop Flights, But There Are Many Connecting Flights! If You Want to Fly Direct, You’ll Need to Search More

That said, it’s good news there are non-stop flights on this route.  I’d recommend planning ahead for this award seat!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

For a Morning View Like This, It’s Worth It!

3.   From Houston

a.   Punta Cana, Dominican Republic

I found lots of award seats to Punta Cana from Houston, including on non-stop flights!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Folks in Houston Can Fly Direct to Punta Cana

Lots of award seats are available in the winter, then taper off closer to summer.  That said, it’s possible to find a flight to the Dominican Republic all year-round!

b.   Montego Bay, Jamaica

I found lots of coach award seats to Jamaica, including on non-stop United Airlines flights, but had trouble finding Business Class award seats on those flights.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

It’s Possible to Find Coach Award Seats on the ~3 Hour Flight to Jamaica, but I Couldn’t Find Any Saver Level Business Class Seats

If you want to fly Business Class, you have nearly 30 other flights to choose from that might have award seats each day, including on Air Canada and Copa Airlines.  I haven’t flown this exact route, but my friend says she doesn’t like to fly on Air Canada’s Business Class if she can help it because they don’t have the best seats and service!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

There Is So Much More to Jamaica Than Beaches. Visit the Beautiful Blue Mountains and See Both the North and South Coasts From the Highest Peak!

Considering flights in April 2016 can be over $1,000, redeeming miles for this route is a fantastic way to use them!

c.   Nassau, Bahamas

Like Jamaica, I was able to find non-stop coach award seats to The Bahamas, but not any low-level Business Class seats.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

I Found Coach Award Seats on the ~3 Hour Non-Stop Flight From Houston to The Bahamas, But No Saver Business Class Seats

But also like before, I found lots of Business Class seats if you’re willing to make a connection.

Considering the flight is only ~3 hours long from Houston, it might be worth it to fly coach, or check flights on Southwest instead.

Need More Chase Ultimate Rewards Points for Your Award Flight?

Link:   Chase Sapphire Preferred

Link:   Chase Ink Plus

Link:   Chase Ink Cash

Link:   Chase Freedom

For a limited time, you’ll earn 50,000 Chase Ultimate Rewards points when you sign-up for the Chase Sapphire Preferred and spend $4,000 on purchases within the 1st 3 months of opening your account.  And the $95 annual fee is waived for the 1st year.

50,000 Chase Ultimate Rewards points is enough for:

  • 1 round-trip coach award flight to the Caribbean from anywhere in the US, Canada, or Alaska
  • A 1-way Business Class flight to the Caribbean from anywhere in the US, Canada, or Alaska

With the Chase Sapphire Preferred card you get 2 Chase Ultimate Rewards points per $1 you spend on travel and dining. 

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Every $1 You Spend on Tropical Drinks Is 2 Points Closer to a Caribbean Holiday!

Because this card has NO foreign transaction fees, it’s a great card to travel with, and to use when you dine out during your Caribbean vacation!

Combine the Ink Plus, Ink Cash, & Freedom With Sapphire Preferred to Visit the Caribbean Faster

If you have the Chase Ink Cash, Ink Bold, or Chase Ink Plus small business cards, you’ll earn 5X Chase Ultimate Rewards points per $1 you spend (5% cash back) at office supply stores and on cell phone, landline, internet, and cable TV services.

And it’s a good idea to use your Chase Ink cards for regular purchases.  You earn 2 Chase Ultimate Rewards points per $1 you spend using your Ink Cash or Ink Plus at gas stations, too!

Use the Freedom 5X (or 10X!) Categories

The Chase Freedom card has rotating quarterly categories that earn 5X Chase Ultimate Rewards points.

And for a limited time, you can earn 10X points (10% cash back) at Amazon from November 23, 2015, through December 31, 2015, on up to $1,500 in spending.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Chase Freedom’s 5X Categories Can Help Get You to Punta Cana or Montego Bay 5 Times Faster!

The Ink Plus, Ink Bold (not open to new applicants), Ink Cash, and Freedom cards are all fantastic options for earning more points on your daily purchases.  And all of them work well together with the Chase Sapphire Preferred!

Note:  The Ink Plus has an annual fee of $95, waived the 1st year.  The Ink Cash and Freedom have NO annual fees.

If you also have a Chase Ink Plus, Chase Ink Bold, or Chase Sapphire Preferred card, you can transfer Chase Ultimate Rewards points earned from the Chase Ink Cash and Freedom cards to airline and hotel partners like British Airways, Hyatt, and United Airlines!

Where to Stay in the Caribbean!

Link:   Where to Stay Using Points in the Caribbean

Link:   Hot Deals – Hotel Credit Cards

Remember there are lots of ways to get cheap or free hotel rooms with points from credit card bonuses and spending!

Folks with Citi Prestige can enjoy their 4th night for free at many hotels!

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

The Holiday Inn Resort Montego Bay Jamaica is 35,000 IHG Points per Night, or Get the 4th Night Free With Your Citi Prestige Card!

You can use points to stay at lots of gorgeous hotels in the Caribbean, like the all-inclusive Holiday Inn Resort Montego Bay Jamaica for 35,000 IHG points a night.

You can use Hyatt points to stay at fantastic all-inclusive resorts in Jamaica!  Hyatt is a Chase Ultimate Rewards transfer partner.

To find hotels that can be booked with points, I use Hotel Hustle (which even shows you if rooms are actually available!) or AwardMapper.

Remember, you can transfer flexible points like Chase Ultimate Rewards or American Express Membership Rewards to different hotel programs.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

Redeem Hilton Points to Book an Award Stay in the Caribbean!

Use Hilton points to stay at gorgeous hotels in the Caribbean.

Read my posts on all the ways to earn Hilton and Hyatt points!

And here are 5 fantastic Starwood hotels in the Caribbean and Mexico to check out.

Note:  Folks who want to book paid stays could check out discount sites like Orbitz, Expedia, or TravelPony for deals.  But remember you won’t get stay credits or points (and might not have your elite status recognized!).

Airbnb

And don’t forget Airbnb is a great way to save money on accommodations, especially for longer stays.

How To Fly Including Business Class To The Caribbean With Chase Sapphire Preferred

You Can Get Great Deals on Airbnb, Even in the Caribbean!

I found a home in Bavaro, Dominican Republic, near Punta Cana, for only $90 a night!

Here are some tips on how to negotiate a better Airbnb price.  And how to find a safe Airbnb where you’ll feel comfortable!

Bottom Line

The Chase Sapphire Preferred card is fantastic for earning valuable and flexible Chase Ultimate Rewards points, which you can transfer at a 1:1 ratio to airline programs like United Airlines, Southwest, and British Airways for award flights to the Caribbean.

United Airlines miles are a convenient way to visit the Caribbean, and so are Southwest points in certain situations.

You can also use British Airways Avios points to get to the Caribbean.  Each program has their sweet spots!

Use your Chase Sapphire Preferred to earn 2X Chase Ultimate Rewards points on travel and dining.  And take it with you when you travel because it doesn’t have foreign transaction fees!

When you pair it with other cards that earn Chase Ultimate Rewards points, like the Chase Ink CashChase Ink Plus, or Chase Freedom, it’s easy to earn even more points on your everyday spending towards an award flight to the Caribbean, like to Punta Cana, Dominican Republic, or Montego Bay, Jamaica!

That’s because when you have the Chase Sapphire Preferred (or Ink Bold or Ink Plus) you can combine all your Chase Ultimate Rewards points.  And then transfer them to airlines for an island vacation!

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2 responses to “How to Fly (Including Business Class!) to the Caribbean With Chase Sapphire Preferred

  1. for Xmas season it is very unlikely to get cheapest economy award tickets to travel to /from Mexico .

    to see how sweet the deals are with Avios : check out PHX to SJD ( Cabos,MX) 4500 points and also DFW to SJD

  2. So as far as Ink Plus giving 5x rewards at office supply stores like Staples and Office Depot: Does that count for ANYTHING purchased there or just SUPPLIES. I could go buy laptops and printers there for big spend if that’s the case….

    Thank you!