$114 Cheap Flights to Cayman Islands
One-way
Departing from
United States
Going to
Cayman Islands
Grand Cayman (GCM)
Cayman Islands • May, 2026
85% AI deal score
$345 $114
Little Cayman (LYB)
Cayman Islands • December, 2025
77% AI deal score
$963 $219
Cayman Brac (CYB)
Cayman Islands • July, 2026
73% AI deal score
$760 $206
Top Cheap Flight Deals to Cayman Islands
Recent round-trip flight deals to Cayman Islands
Sun, Dec 21 - Wed, Dec 24
Cheapest
Aspen (ASE) - Grand Cayman (GCM)
United Airlines airlines • 1 stop • Houston (IAH)
Grand Cayman (GCM) - Aspen (ASE)
United Airlines airlines • 2 stops • Houston (IAH), Denver (DEN)
$594
Sun, Dec 21 - Wed, Dec 24
Aspen (ASE) - Grand Cayman (GCM)
United Airlines airlines • 1 stop • Chicago (ORD)
Grand Cayman (GCM) - Aspen (ASE)
United Airlines airlines • 2 stops • Houston (IAH), Denver (DEN)
$596
Sun, Dec 14 - Sun, Dec 21
Aspen (ASE) - Grand Cayman (GCM)
United Airlines airlines • 2 stops • Denver (DEN), Houston (IAH)
Grand Cayman (GCM) - Aspen (ASE)
United Airlines airlines • 1 stop • Chicago (ORD)
$1,133
Wed, Dec 3 - Mon, Dec 22
San Angelo (SJT) - Grand Cayman (GCM)
Alaska Airlines, Inc. airlines • 3 stops • Dallas (DFW), Seattle (SEA), New York (JFK)
Grand Cayman (GCM) - San Angelo (SJT)
Cayman Airways airlines • 3 stops • Miami (MIA), Portland (PDX), Dallas (DFW)
$2,133
Fri, Dec 26 - Fri, Jan 2
Bradford (BFD) - Grand Cayman (GCM)
Southern Airways airlines • 1 stop • Washington, D.C. (IAD)
Grand Cayman (GCM) - Bradford (BFD)
United Airlines airlines • 2 stops • Washington, D.C. (IAD), Pittsburgh (PIT)
$4,164
The cheapest time to fly to Cayman Islands
Ready to jet to Cayman Islands on a budget? Check out these popular routes with surprisingly cheap fares (one-way prices):
Last-Minute Flights to Cayman Islands
Need to get to Cayman Islands ASAP? Even if you're booking a flight on short notice, there are often last-minute deals available:
Next 2 weeks deals
Last Minute Cayman Islands Deals
Book flights to the Cayman Islands starting from $282, departing in the next two weeks.
⌛ Last-Minute
Providence - KY
A great last-minute steal for a cross-country flight.
Found 1 week ago
$282
one-way
Facts About Flights to Cayman Islands
To help you plan your journey, here are some quick Cayman Islands flight facts and tips.
Cayman Islands airports
The Cayman Islands are served by three airports: Owen Roberts International Airport (GCM) on Grand Cayman, Charles Kirkconnell International Airport (CYB) on Cayman Brac, and Edward Bodden Airfield (LYB) on Little Cayman. Owen Roberts is the main international gateway, handling the vast majority of tourist and business traffic with connections to major North American and Caribbean hubs. Charles Kirkconnell serves primarily domestic flights and some regional routes, providing essential connectivity for Cayman Brac residents and visitors. Edward Bodden Airfield, also mainly for domestic flights, links Little Cayman to the other islands, crucial for the small population and eco-tourism focused on the island's natural beauty.
Owen Roberts International (GCM)
Grand Cayman, Cayman Islands
Charles Kirkconnell International (CYB)
Cayman Brac, Cayman Islands
Edward Bodden Airfield (LYB)
Little Cayman, Cayman Islands
Pro tip: search “Cayman Islands (Any)” to see fares to all Cayman Islands airports – sometimes one is cheaper than the others on your dates.
Insights for flights to Cayman Islands
Cheapest airport
Owen Roberts International Airport (GCM)
Owen Roberts International Airport (GCM) is the primary airport serving Grand Cayman, located near George Town. While it's not the cheapest airport to fly to *all* the time, it frequently offers competitive rates and is the most convenient option since it is the main airport in the Cayman Islands! Keep an eye on flights to GCM for your tropical getaway; you might just snag a fantastic deal!
Nonstop vs. 1-stop
20+ cities
While not a major hub, the Owen Roberts International Airport (GCM) in the Cayman Islands serves as a connecting point for several routes, with popular connections to and from destinations like Miami, Tampa, and Kingston.
GCM Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
GCM airport insights
Best days to catch a deal
Tue, Wed
Based on the provided data, Tuesday has the highest count, indicating it's the most frequent day for finding cheap deals to Owen Roberts International Airport. Thursday and Saturday also show a relatively high frequency of deals compared to Monday and Friday.
Avg. deal survival time
14.8 hours
Deals for flights from Owen Roberts International Airport typically last around 14.8 hours. You'll want to book quickly if you see a deal you like, as these deals don't stay available for very long.
Rare deal frequency
10 deals
We discovered 10 rare deals for Owen Roberts International Airport in the last month, all achieving an AI Deal Score of 90 or higher. These exceptional opportunities typically arise from mistake fares, exclusive promotions, or substantial discounts.
Average price drop
-10%
The average price drop for flights to Owen Roberts International Airport is 9.7%. This means that travelers can potentially save almost 10% on their flights by monitoring prices and booking at the right time.
Next 4 weeks: deal forecast
Owen Roberts Intl. Airport: Next Month Forecast
Based on trends, flight prices to Owen Roberts International Airport are expected to remain relatively stable in the coming month. There are no significant price drops or increases anticipated as of November 15, 2025.
Top 5 biggest price drops (last 3 months)
Found on November 10
Penticton - GCM
$2,325 → $233
90%
Found on November 14
Greater Sudbury - GCM
$845 → $217
74%
Found on November 13
San Andrés - GCM
$1,010 → $277
73%
Found on November 13
Charlottetown - GCM
$1,050 → $294
72%
Found on November 12
Paris - GCM
$1,900 → $850
55%
Check these nearby airports too
Looking for more options? These airports near GCM sometimes drop rare deals too:
Charles Kirkconnell International (CYB)
~9 rare deals/month
Owen Roberts International (GCM)
~10 rare deals/month
San Rafael Airport (LOB)
~5 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially CYB and GCM for long-haul deal surprises.
When Is the Best Time to Fly to Cayman Islands
Timing is everything when hunting for cheap flights. Here are data-backed insights on the best times to fly to Cayman Islands:
Cheapest month
September
Cheapest month
The cheapest month to fly to Grand Cayman is September. The weather is still fantastic, with warm temperatures and plenty of sunshine. Plus, you'll avoid the peak tourist crowds, making for a more relaxed and budget-friendly getaway.
Best day to book
Sunday
Best day to book
The best day to book a flight to Grand Cayman is Sunday. Airlines often release deals early in the week, so catching them on Sunday gives you first dibs. Plus, you'll have the whole week to plan your trip with that flight secured!
Cheapest days to fly
Tuesday
Cheapest days to fly
The cheapest days to fly to Grand Cayman are Tuesdays. Mid-week flights are generally less popular with business travelers, driving down prices. By flying on Tuesday, you can save some serious cash for enjoying the island life.
Advance booking sweet spot
2 months
Advance booking sweet spot
The advance booking sweet spot for flights to Grand Cayman is around 2 months before your trip. This timeframe balances the availability of flights with the chance of snagging a good deal. Booking too early or too late might mean you miss out on the best prices, so plan ahead!
Seasonal considerations
Cayman Islands Airports & Ground Transportation
One big question for travelers is which Cayman Islands airport to fly into. Here’s a quick guide to Cayman Islands’s airports and how to get to the city from each:
Owen Roberts International Airport (GCM)
Welcome to Owen Roberts International Airport, your gateway to Grand Cayman's sun-kissed beaches and vibrant culture! Just a hop, skip, and a jump (about 1 mile) from George Town, this airport offers a cozy and convenient start to your island adventure. Once you land, you'll find amenities such as duty-free shops, restaurants serving up local flavors, and car rental services to start exploring the island. The airport has undergone recent expansions to better accommodate the increasing number of visitors, ensuring a smoother travel experience. Getting into George Town is a breeze with readily available taxis and pre-booked shuttle services right outside the terminal.
Tip: Arriving on a weekend? Pre-booking your taxi or shuttle is highly recommended to avoid any wait times!
Other airports
While Grand Cayman boasts its own well-equipped airport, Owen Roberts International Airport (GCM), travelers might consider flying into nearby cities for potential deals. However, keep in mind the extra leg of the journey! Getting from other cities to Grand Cayman typically involves a connecting flight, as there aren't direct ferries or easy road access.
What to Do in Cayman Islands
Cayman Islands isn’t just about getting there – it’s about enjoying the country once you arrive! Here are some top things to do in Cayman Islands, organized by interest:
Sightseeing & landmarks
Get ready to explore Grand Cayman's iconic spots! From the stunning Seven Mile Beach to the historic Pedro St. James Castle, there's a postcard-perfect view waiting around every corner. Don't forget to visit Stingray City for a truly unforgettable experience!
Arts & culture
Immerse yourself in the vibrant local culture of Grand Cayman. Explore the National Gallery to admire Caymanian art or catch a performance at the Harquail Theatre. Be sure to check out local craft markets for unique souvenirs!
Food & nightlife
Indulge in the flavors of the Caribbean! Grand Cayman boasts a diverse culinary scene, from fresh seafood shacks to upscale dining experiences. As the sun sets, the island comes alive with lively bars and beachfront lounges perfect for a night of fun.
Shopping & fashion
Shop 'til you drop in Grand Cayman! Discover duty-free treasures and high-end boutiques in George Town. Looking for something unique? Explore the local artisan shops for handcrafted jewelry, art, and souvenirs.
Nearby getaways
Ready for a quick escape? Hop on a boat to explore the sister islands of Cayman Brac and Little Cayman. Discover even more secluded beaches, incredible diving spots, and untouched natural beauty just a short trip away!
No matter your interest – be it art, food, nightlife, or nature – Cayman Islands has something for everyone. And the best part? Many events and attractions refresh throughout the year, so there’s always something new to experience each visit.
Events in Cayman Islands This Month
cayman fiesta live - oasis weekend series
Get ready for Cayman Fiesta Live 2025 at Compass Green! Rick Ross will be headlining on Friday, promising an epic weekend of music and great vibes across three parties. Don't miss out on this unforgettable event!
happy fri-yay — vines to ocean
Kick off your weekend with an extended Happy Hour every Friday! Enjoy special prices starting an hour early, including $8 wines, $5 beers, $10 cocktails, $3.50 fresh oysters, and $5 oyster shooters.
vital cayman studio class
Join Rachel Lesley for a Vital Cayman Studio Class at Vital Spin & Yoga Den on November 9 at 10:00 AM EST. Enhance your well-being with this invigorating yoga session.
sushi saturday — vines to ocean
Indulge in our weekend sushi special and savor your favorite specialty roll, sashimi, or nigiri, accompanied by a glass of wine for just $22 KYD plus gratuities. Enjoy as many rounds as you like!
Cayman Islands Weather
Weather in Cayman Islands
Sat, Nov 15
40%
29° 26°
40%
Sun, Nov 16
Frequently Asked Questions About Flights to Cayman Islands
Pro Tips for Finding Cheap Flights to Cayman Islands
Finally, to wrap up, here’s a cheat sheet of pro tips that experienced travelers use to save on Cayman Islands flights:
Be Flexible with Your Dates: Flying mid-week or during the off-season can seriously slash ticket prices. Think of it as playing travel roulette, but with better odds of winning a cheap flight!
Set Up Price Alerts: Let RatePunk be your hawk-eyed buddy! Set up price alerts for your desired dates and destinations, and pounce the moment prices drop. It's like having a personal flight deal fairy!
