10 Best Airlines to Fly to Grand Cayman (2024 Updated)

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Thinking of swapping your couch for a beach chair? Our guide on the best airlines to Grand Cayman is your ticket to finding the perfect flight for your Caribbean escape. From budget-friendly options to luxury in the skies, we’ve covered everything to make your choice as breezy as the Cayman winds. Keep reading to discover the best airlines to fly to Grand Cayman in 2024.

Imagine crystal-clear waters, endless stretches of sandy beaches, and an island vibe that instantly soothes your soul. Welcome to Grand Cayman, a slice of heaven nestled in the Caribbean Sea. For those bitten by the travel bug, this destination is a must-visit. But, let’s talk about getting there – because the journey is just as important as the destination, right?

Choosing the right airline can make all the difference. Whether you’re seeking top-notch comfort, budget-friendly options, or convenient flight schedules, there’s an airline that fits your travel style. From the moment you board, the adventure begins. Picture yourself sipping a tropical drink, flipping through a travel magazine, and daydreaming about the warm Cayman sun.

So, buckle up, fellow wanderers! We’re about to embark on a virtual tour of the best airlines to whisk you away to Grand Cayman. Each one offers something unique, ensuring your trip starts on a high note. Whether you’re a seasoned globetrotter or a first-time visitor to the Caribbean, these airlines are your ticket to an epic island getaway. Ready to find out which airline will be your travel buddy? Let’s go!

The best airlines to fly to Grand Cayman right now

#1 tip to find cheap flights to Grand Cayman

Looking for the cheapest flights to Grand Cayman? This is a game-changer: Going (formerly Scott’s Cheap Flights).

Here’s the deal: Sign up for free email alerts, set your departure and destination, and boom – you’ll get alerts for insanely cheap flights. Mistake fares? Deep discounts? They’ve got it all.

I’ve saved thousands using Going. Recently, I even found a $269 roundtrip fare from Boston to Grand Cayman (Owen Roberts International Airport) during the spring. Not bad!

Want even more deals? Their $49/year premium version is well worth it- just one discounted flight pays the whole thing. And if you’re into business/first class, you’ll definitely want to sign up for their Elite version, which saved me over $5,000 in 2023 alone. Trust me, it’s a small price for massive savings.

Now, let’s discuss the best way to fly to Grand Cayman in 2024.

Best Airlines to Fly to Grand Cayman

We’ve rounded up the best airlines to make your journey as stunning as the destination itself. From cozy seats to amazing deals, find out which airline will be your perfect travel partner to this island paradise.

1. Cayman Airways

If you’re looking for the best airline to Grand Cayman, look no further than Cayman Airways. This airline is the national flag carrier of the Cayman Islands, deeply rooted in the region’s culture and history since its inception in 1968.

Based at Owen Roberts International Airport in Grand Cayman, Cayman Airways connects the islands to key destinations like Miami, New York, Tampa, and Chicago. Their fleet, including the Boeing 737 MAX 8, is tailored for both comfort and efficiency.

For the ultimate journey to Grand Cayman, Cayman Airways stands as the optimal choice, offering exceptional service and reliability.
For the ultimate journey to Grand Cayman, Cayman Airways stands as the optimal choice, offering exceptional service and reliability.

What sets this Grand Cayman airline apart? For starters, they offer a generous baggage policy. Economy passengers can check in two bags for free, each up to 55 lbs. This is quite a perk in today’s travel world. And for a taste of the islands, they serve complimentary Rum Punch on international flights.

In terms of seating, Economy Class provides sufficient legroom, and Business Class offers additional space and comfort. While in-flight entertainment is limited to reading material, the real excitement is the anticipation of arriving in paradise.

Ticket prices are competitive, offering value for money. From Miami, the typical cost of a round trip flight to Grand Cayman is $389. Plus, their frequent flyer program, Sir Turtle Rewards, adds extra value for regular passengers.

2. American Airlines

Next up, let’s fly with American Airlines, a major player in the aviation world. As the nation’s largest passenger airline, it offers nearly 6,700 daily flights to over 50 countries. So, what makes it a go-to for travelers heading to Grand Cayman?

First off, American Airlines stands out with its range of fare classes, making it one of the best airlines to Grand Cayman for no matter your budget. From the ultra-luxurious Flagship First to the budget-friendly Basic Economy, there’s something for every traveler. And if you’re flying from Chicago to Grand Cayman, you might find roundtrip tickets for about $398 – a sweet deal for such a journey!

American Airlines excels with diverse fare classes, ensuring an ideal choice for Grand Cayman, catering to varied budgets.
American Airlines excels with diverse fare classes, ensuring an ideal choice for Grand Cayman, catering to varied budgets.

The airline’s hubs are spread across the US, including Dallas/Fort Worth, Charlotte, and Chicago, making it super accessible. If you’re flying to Grand Cayman, you’ll likely connect through one of these major hubs.

Now, let’s talk perks. In higher fare classes, expect lie-flat seats, chef-inspired dining, and even amenity kits for a touch of luxury. Even in Economy, you’re treated to free snacks and entertainment. And for those who love to stay connected, Wi-Fi is available on select flights.

American Airlines is also known for its flexible flight change policies. Life’s unpredictable, and they get that. Plus, their baggage policy is pretty straightforward – a free carry-on and personal item for all, with more generous allowances in premium classes.

3. British Airways

Let’s soar with British Airways, where every journey is infused with a touch of classic British elegance. With roundtrip flights from London to Grand Cayman typically around $823, it’s a journey that promises both value and a high-quality experience.

At the core of the British Airways experience is a commitment to making every journey special. Their main hub at London Heathrow is just the beginning of a network that connects travelers to the world’s most exciting destinations, including the serene beaches of Grand Cayman.

British Airways prioritizes sustainability and community support as crucial pillars, reflecting a commitment to responsible practices and social engagement.
British Airways prioritizes sustainability and community support as crucial pillars, reflecting a commitment to responsible practices and social engagement.

The airline distinguishes itself with generous baggage allowances. Traveling with family? Children over two enjoy the same baggage privileges as adults, easing the stress of packing for a family vacation.

Onboard, the culinary experience is a highlight. Enjoy selections from a menu designed by Michelin-starred chef Tom Kerridge, bringing a taste of Britain to the skies. Whether relaxing in Economy with a selection of movies or stretching out in a flat-bed seat in Business Class, the service is consistently British – refined, attentive, and with a classic charm.

Sustainability and community support are also key pillars for British Airways. Their proactive steps in reducing emissions and waste align with the values of environmentally conscious travelers, adding a responsible dimension to your journey.

With a range of travel cabins, British Airways caters to diverse preferences and budgets. From the luxury of First Class to the practicality of Economy, each class is thoughtfully designed to enhance the travel experience.

4. Delta Airlines

Delta Airlines, one of the airlines that fly to Grand Cayman, has come a long way since its start as a crop-dusting operation in 1925. Today, it’s one of the largest airlines globally, flying to 300 destinations in over 50 countries. With major hubs like Atlanta and New York City, Delta is a go-to for many travelers.

A roundtrip flight from Chicago to Grand Cayman typically costs about $342, offering a blend of affordability and quality service. Delta’s variety of fare classes caters to different needs and budgets. From the no-frills Basic Economy to the luxurious Delta One, there’s a choice for every traveler.

Delta's renowned flexibility adds another significant advantage, enhancing the overall appeal and positive reputation of the airline.
Delta has a positive overall appeal and reputation internationally.

It’s the little things that make Delta Airlines stand out. In Delta Comfort+, you get extra legroom, priority boarding, and additional snacks. Premium Select steps it up with larger seats and enhanced amenities. And in Delta One, expect lie-flat seats and a premium dining experience.

Delta’s reputation for flexibility is also a big plus. Their change and cancellation policies are quite forgiving, offering eCredits for future travel if plans change. This flexibility, combined with a range of fare options, makes Delta a popular choice for trips to Grand Cayman.

INSIDER TIP: Again, I highly recommend signing up for Going.com (Scott’s Cheap Flights) to find the best deals. Last year, I got an email alert on a $291 roundtrip fare from Boston to Grand Cayman with Jetblue. The premium version is 100% worth the money, but I would at least sign up for the free version to save big on airfare this year.

5. Air Canada

One of the best airlines to fly to Grand Cayman, Air Canada offers a range of experiences that cater to different traveler needs. If you’re flying from Chicago, a one-way ticket typically costs around $312, striking a balance between affordability and comfort.

Air Canada stands out among its peers thanks to its variety of fare options. Whether you’re a budget-conscious traveler or someone who enjoys a bit more luxury, they’ve got you covered. Their fare classes range from Economy Basic, the most budget-friendly option, to Business Class, where luxury takes the front seat.

Air Canada, among the finest airlines for Grand Cayman, provides diverse experiences tailored to various traveler needs
Air Canada, among the finest airlines for Grand Cayman, provides diverse experiences tailored to various traveler needs

Economy Basic is great for those who just need a seat and are traveling light. It’s the no-frills, cost-effective way to travel. But if you’re looking for more perks, the Economy Standard or Flex might be more your style, offering more Aeroplan points and flexibility.

For those who prefer a bit more legroom and comfort, Premium Economy offers a more spacious experience. And if you’re all about luxury and comfort, Business Class is where it’s at with lie-flat seats and top-notch in-flight service.

Air Canada’s hubs, including Toronto and Vancouver, make it a convenient option for travelers from various locations. In-flight, expect a range of entertainment options and, depending on your fare class, some tasty meal choices too.

6. JetBlue

A relatively newer player in the skies, JetBlue has quickly become a favorite for many travelers, especially those looking for the best airline to fly to Grand Cayman. Founded in 2000 in New York City, JetBlue now serves over 100 destinations with a focus on customer satisfaction.

What’s cool about JetBlue? Well, for starters, their ticket prices are very affordable. A one-way ticket from New York to Grand Cayman typically goes for about $103. That’s a deal hard to beat, especially considering what you get for the price. They’ve got a variety of ticket options too, from the budget-friendly Blue Basic to the more luxurious Mint service. Mint is their take on first class, with lie-flat seating and fancy dining.

JetBlue stands out with its affordability, making it cool for travelers seeking budget-friendly options without compromising on service quality.
JetBlue stands out with its affordability, making it cool for travelers seeking budget-friendly options without compromising on service quality.

JetBlue’s approach to flying is all about making the experience better for everyone. They offer the most legroom in coach of all domestic airlines, which is a big deal if you like to stretch out. Plus, every seat gets free WiFi, DIRECTV, SiriusXM radio, and movies.

JetBlue operates out of several major hubs, including New York, Boston, and Fort Lauderdale, making it a convenient option for many travelers. Their focus on key routes, like New York to the Caribbean, aligns perfectly with those looking to escape to sunny Grand Cayman.

Their baggage policy is pretty straightforward. Depending on your ticket class and loyalty status, you might even score free checked bags. And speaking of loyalty, their TrueBlue program is worth checking out if you fly JetBlue often.

7. United Airlines

With a history that stretches back to 1926, United Airlines has grown into one of the largest airlines in the world, offering flights to a vast array of destinations. If you’re flying to Grand Cayman, United is a solid choice.

A roundtrip ticket from Chicago to Grand Cayman typically costs around $351, which is pretty reasonable considering United’s extensive network and service quality. They’ve got hubs in major cities like Chicago, Denver, and San Francisco, making them a convenient option for travelers from all over.

When heading to Grand Cayman, United proves to be a reliable and solid choice for a satisfying travel experience.
When heading to Grand Cayman, United proves to be a reliable and solid choice for a satisfying travel experience.

United has a range of fare classes to suit different travel needs and budgets. From Basic Economy for those looking to save a few bucks, to Polaris Business Class for those who like to travel in style, there’s something for everyone.

In-flight, United offers amenities that can make a long flight more enjoyable. Think free Wi-Fi on most flights, a variety of entertainment options, and a range of food and beverage choices. Plus, if you’re flying Polaris, get ready for some serious comfort with lie-flat seats and top-notch service.

United’s frequent flyer program, MileagePlus, is another perk. It’s been around since 1981 and offers great benefits for loyal customers. And if you’re into airline alliances, United was a founding member of Star Alliance, so you’ve got options for racking up those miles.

8. WestJet

WestJet, Canada’s second-largest airline, is a fantastic choice for those looking for the best flight to Grand Cayman. Based in Calgary, Alberta, WestJet has been making waves in the airline industry with its friendly service and comfortable travel experience.

A roundtrip ticket from Toronto to Grand Cayman typically costs about $544. While not the cheapest, WestJet’s reputation for top-notch service makes it worth considering. They fly to a variety of destinations, including major cities in Canada, Europe, the Caribbean, and Asia.

For the ultimate flight to Grand Cayman, consider WestJet, Canada's second-largest airline, renowned for its exceptional service and reliability.
For the ultimate flight to Grand Cayman, consider WestJet, Canada’s second-largest airline, renowned for its exceptional service and reliability.

WestJet offers a range of in-flight amenities, including movies, TV shows, and games, ensuring your flight is more than just a way to get from point A to B. Plus, their digital travel assistant, Juliet, can help make your travel planning a breeze.

WestJet’s baggage policy is pretty straightforward – one carry-on bag and one personal item. But remember, if your carry-on exceeds the limits, you’ll need to check it and pay a fee. They also have lounges in major airports, offering a comfortable space to relax before your flight.

For those flying within Canada or on long-haul flights, WestJet provides a comfortable and enjoyable experience. Their EconoFlex and Premium Class offerings are great for those seeking extra comfort and convenience.

9. Sun Country Airlines

Sun Country Airlines, a Minnesota-based carrier, has evolved into a budget airline, offering a unique blend of low-cost and comfort. If you’re eyeing the best airlines to fly to Grand Cayman, Sun Country is a contender, especially for those flying from Minneapolis, where a one-way ticket to Grand Cayman typically costs around $203.

Sun Country stands out in the budget airline space. Unlike other low-cost carriers, Sun Country offers a more comfortable in-flight experience. Their seats, while slimmer, provide better padding than you might find on other budget airlines. Plus, they haven’t skimped on legroom, making the journey more comfortable, especially for taller passengers.

For the optimal Grand Cayman flight experience, Sun Country stands out as a top contender among the best airlines.
For the optimal Grand Cayman flight experience, Sun Country stands out as a top contender among the best airlines.

The airline operates a fleet of Boeing 737s, ensuring a consistent experience across its flights. While they’ve transitioned away from a full-service model, Sun Country still offers complimentary drink service, a rarity among budget carriers. For those looking for a snack or a stronger drink, options are available for purchase, including local Minnesota favorites.

One thing to note is that Sun Country has adopted an a la carte pricing model. This means you pay for what you need, like carry-ons, checked bags, and seat selection. While this can add up, it also allows for a more customized travel experience, tailored to your needs and budget.

10. Southwest Airlines

Known for its unique approach in the low-cost carrier space, Southwest Airlines offers a distinct experience. If you’re flying from Houston to Grand Cayman, expect to pay around $235 for a one-way ticket. But what makes Southwest stand out?

Firstly, Southwest’s baggage policy is a traveler’s dream. They allow two checked bags for free, a rarity in today’s airline industry. Just keep in mind the size and weight limits. This generous policy can save you a pretty penny, especially if you’re the type to pack heavy.

With its expansive network, Southwest Airlines offers the convenience of reaching a multitude of major cities throughout the United States.
With its expansive network, Southwest Airlines offers the convenience of reaching a multitude of major cities throughout the United States.

Southwest operates a single type of aircraft – the Boeing 737. This simplifies maintenance and operations, contributing to lower costs. Their fleet is impressive, with over 800 jets, making them a major player in the US.

Now, let’s talk about boarding. Southwest doesn’t assign seats. Instead, you’re given a boarding group and number, and you pick your seat when you board. Want to ensure an early boarding position? You might consider their EarlyBird check-in option, starting at $15. It’s a different system, but many travelers love the flexibility it offers.

In-flight, Southwest provides complimentary entertainment streaming through its app. For $8 a day per device, you can access WiFi on WiFi-enabled aircraft. This is a nice touch for staying connected or entertained during your flight.

Southwest’s hubs include major airports like Baltimore/Washington International, Dallas Love Field, and Denver International. This extensive network means you can fly Southwest to most major cities in the US.

Frequently Asked Questions About the Best Airlines to Fly to Grand Cayman

In our FAQ section, discover insights on the best airlines to fly to Grand Cayman, ensuring your trip starts as smoothly as it ends.

What is the best airline to fly to Grand Cayman?

The best airline to fly to Grand Cayman depends on your preferences. For luxury and comprehensive service, British Airways is a top choice. If you’re looking for a budget-friendly option with generous baggage policies, Southwest Airlines is ideal. Cayman Airways, being the national carrier, offers direct and authentic experiences. Each airline has its unique advantages, so the best choice varies based on your priorities like cost, comfort, and convenience.

Which US cities fly directly to Grand Cayman?

Several US cities offer direct flights to Grand Cayman, making it a convenient Caribbean getaway. Major cities like Miami, New York, and Chicago have direct routes. Airlines like American Airlines, Delta, and United operate these flights. The availability of direct flights may vary seasonally, so it’s wise to check current schedules when planning your trip.

Numerous top-rated airlines operate flights to Grand Cayman, each boasting distinctive strengths and offerings to cater to varied traveler preferences.
Numerous top-rated airlines operate flights to Grand Cayman, each boasting distinctive strengths and offerings to cater to varied traveler preferences.

What is the cheapest month to go to Grand Cayman?

The cheapest month to visit Grand Cayman is typically September. This is during the Caribbean’s off-peak season, coinciding with hurricane season. While there’s a higher chance of rain, you’ll find lower prices on flights and accommodations. It’s a trade-off between cost and weather, so if you’re looking to save money and don’t mind a bit of unpredictability in weather, September is your month.

What are the best airlines from the US to Grand Cayman?

The best airlines from the US to Grand Cayman include major carriers like American Airlines, Delta, and United Airlines. These airlines offer a mix of comfort, reliability, and extensive flight networks. Southwest Airlines is another great option, known for its customer-friendly policies like free checked bags. Each airline offers different advantages, whether it’s flight frequency, price, or onboard amenities.

Can you fly direct to Grand Cayman from the West Coast of the US?

Direct flights from the West Coast of the US to Grand Cayman are limited. Most flights from cities like Los Angeles or San Francisco involve at least one stopover, commonly in hubs like Miami or Houston. Direct flights are more readily available from East Coast and Southern US cities.

What airlines offer the best deals to Grand Cayman?

For the best deals to Grand Cayman, budget airlines like Southwest and Sun Country Airlines often have competitive pricing. Southwest is particularly popular for its two free checked bags policy. Additionally, keep an eye on seasonal sales and promotions from other major airlines like American Airlines and Delta, as they occasionally offer attractive deals.

In this extensive guide, we've examined top airlines for Grand Cayman travel, each providing distinct amenities, service, and travel quality.
In this extensive guide, we’ve examined top airlines for Grand Cayman travel, each providing distinct amenities, service, and travel quality.

Are there luxury flight options to Grand Cayman?

For luxury flight options to Grand Cayman, consider airlines like British Airways or the Business and First Class services of American Airlines and Delta. These airlines offer premium seating, enhanced dining experiences, and additional amenities for a more luxurious journey. The level of luxury varies, so it’s worth comparing the specific services offered on your travel dates.

How long are flights to Grand Cayman from major US cities?

Flight durations to Grand Cayman vary. From Miami, it’s about an hour and a half, making it one of the shortest routes. Flights from New York or Chicago typically take around four hours. From the West Coast, like Los Angeles, expect the journey to be longer, usually around 7 hours, including stopovers, as direct flights are rare.

Grand Cayman Airlines in 2024: A Recap

In conclusion, there are many top-rated airlines that fly to Grand Cayman, each with its own unique strengths and offerings. From the luxurious amenities of Delta Airlines to the affordable fares of Japan Airlines, there is an airline out there to suit every traveler’s needs and budget.

Whether you’re looking for exceptional customer service, state-of-the-art technology, or an extensive network of routes, Grand Cayman has it all. So, whether you’re planning a once-in-a-lifetime adventure or a quick weekend getaway, be sure to consider these top airlines for your journey to Grand Cayman. And don’t forget to sign up for Scott’s Cheap Flights to get the best possible deal on airfare this year!

Happy Travels! – Jon

Read next: Scott’s Cheap Flights Review

The best airlines to fly to Grand Cayman for all types of travelers
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