Skip to content

JetBlue Deal alert: Flights to the Cayman Islands from NYC, Chicago and more from $301

April 02, 2022
5 min read
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

A summer vacation in the idyllic Cayman Islands kind of sells itself. But when you can grab a plane ticket at a great price, paradise suddenly looks just a bit better, doesn't it?

JetBlue currently has tickets to the legendary Caribbean island chain on sale, with the best prices available for travelers in New York City looking to escape the concrete jungle for a few days on some of the best beaches on the planet. There are some sweet deals for flights out of Chicago and Cleveland, too.

The sale applies to JetBlue's Blue Basic tier (basic economy), which means no carry-on bag. You can pay to upgrade to the Blue economy tier, which gets you free seat selection and a carry-on, but in some instances it may be cheaper just to pay for the checked bag.

Sign up for our daily newsletter

Want more TPG news delivered every morning to your inbox? Sign up for our daily newsletter.

Our thanks to Secret Flying for tipping us off to this great travel deal.

The very best deals in this sale are for travel between April and June. As always, a flexible travel schedule will help you score the best prices.

Deal basics

Airline: JetBlue
Routes: Boston, Chicago, Cleveland, Fort Lauderdale and New York to Grand Cayman, Cayman Islands
How to book: Search Google Flights and book directly through the airline
Travel dates: April — June

Cushion sea stars (Oreaster reticulatus) in shallow water off the south side of Little Cayman. (Photo by Stephen Frink/Getty Images)

Sample flights

You can book a nonstop flight in late April from New York City (JFK) to Grand Cayman (GCM) for $303. Again, it's a Blue Basic ticket, so keep in mind a checked bag will cost you $60. It's better to do that than pay $70 to upgrade.

(Screenshot courtesy of Google Flights)

You can find the same fare for travel between Kennedy Airport and Grand Cayman across most of May and June.

(Screenshot courtesy of Google Flights)

One of the best deals we found was from Cleveland (CLE) to Grand Cayman. You can book a late April trip for just $356, a huge discount from typical prices. Adding to the appeal of this fare is that a checked bag only costs $30. Also, upgrading to a Blue tier ticket costs just $48, which gets you a free checked bag and carry-on.

(Screenshot courtesy of Google Flights)

Chicago (ORD) to the Caymans in late April certainly sounds appealing. Especially when you can score a round-trip ticket for just $438, a nice discount from typical fares. Your first checked bag with this ticket will cost you just $30. Something to consider, however, is that upgrading to Blue will cost you just $43, and it comes with a free checked bag and a carry-on.

(Screenshot courtesy of Google Flights)

We also found good prices on round-trip flights from Boston (BOS) to Grand Cayman in late May. Again, this is another example where it would save you money -- nearly $60 -- to pay for a checked bag than paying for the upgrade to the Blue Tier.

(Screenshot courtesy of Google Flights)

If you live in south Florida and want some more tranquil beach time in late April than you'll find on South Beach or Las Olas in Florida, you can fly from Fort Lauderdale (FLL) to Grand Cayman for just $301 nonstop. Also, upgrading to the Blue tier will only cost you $40, which is $20 cheaper than the cost of checking your bag.

(Screenshot courtesy of Google Flights)

Related: After 2 years, cruise ships are finally returning to the Cayman Islands

Maximize your purchase

Pay with: The Platinum Card® from American Express for 5 points per dollar on airfare booked directly with the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year), the Citi Prestige® Card for 5 points per dollar on airfare, the Citi Premier® Card or Chase Sapphire Reserve for 3 points per dollar on air travel, the American Express® Gold Card for 3 points per dollar on airfare when booked directly with the airline or through Amex Travel, or the Chase Sapphire Preferred Card for 2 points per dollar on travel.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Featured image by Getty Images
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

TPG featured card

Best starter travel card
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards

1 - 3X points
3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
1XEarn 1 Point per $1 spent on all other purchases

Intro offer

Earn 80,000 ThankYou® points60,000 points
For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

Annual Fee

$95

Recommended Credit

670-850
Excellent, Good
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases
Best starter travel card
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
1XEarn 1 Point per $1 spent on all other purchases
  • Intro Offer
    For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

    Earn 80,000 ThankYou® points
    60,000 points
  • Annual Fee

    $95
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    670-850
    Excellent, Good

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases