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C$ 139+ Cheap flights to the Cayman Islands

— GCM
24 Oct — 31 Oct1
1 adult
1 adult, Economy, 0 bags

Flights to Cayman Islands in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Cayman Islands

Tue 20/109:40 a.m. -
Nonstop4h 05m
Sat 24/101:45 p.m. -
Nonstop4h 10m
Deal found 23/9C$ 334
Sat 26/99:40 a.m. -
Nonstop4h 05m
Sat 3/101:45 p.m. -
Nonstop4h 10m
Deal found 20/9C$ 337
Sat 3/106:45 a.m. -
Nonstop4h 00m
Thu 8/1012:25 p.m. -
Nonstop4h 05m
Deal found 21/9C$ 356
Sat 24/109:40 a.m. -
Nonstop4h 05m
Sun 25/102:35 p.m. -
Nonstop4h 10m
Deal found 20/9C$ 358
Sat 26/96:45 a.m. -
Nonstop4h 00m
Sat 3/1010:40 a.m. -
Nonstop4h 05m
Deal found 21/9C$ 359
Mon 5/108:25 a.m. -
Nonstop4h 00m
Sat 10/1011:25 a.m. -
Nonstop4h 05m
Deal found 20/9C$ 365

Find flights to Cayman Islands

Explore the Cayman Islands
Flights to George Town
Flights to Cayman Brac

Find flight deals to Cayman Islands

Round-trip from

C$ 334

One-way from

C$ 139

Popular in

August

Cheapest in

January

Average price

C$ 502

Good round-trip deal

C$ 371 or less

Good one-way deal

C$ 185 or less
WestJet
  • WestJet
  • 20/10-24/10
  • Nonstop
  • 8h 15m total
  • Toronto to George Town
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Air Canada
  • Air Canada
  • 3/10-31/12
  • Nonstop
  • 4h 00m total
  • Toronto to Cayman Islands
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Highest demand for flights based on searches. 15% potential increase in price (C$ 101 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 25 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Toronto to Cayman Islands.
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Price to beat on a one-way flight from Toronto to Cayman Islands.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights to the Cayman Islands that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Thu 28/1

3:35 p.m.-1:45 p.m.

1 stop22h 10m

George Town Owen Roberts Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 192
Quickest round-trip

TorontoCayman Brac

YYZ Toronto Pearson Intl - CYB Cayman Brac Gerrard-Smith

YYZCYB

Toronto Pearson Intl

Thu 5/11

10:15 a.m.-5:50 p.m.

1 stop7h 35m

Cayman Brac Gerrard-Smith

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 351

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Tue 26/1

6:40 p.m.-1:15 p.m.

1 stop18h 35m

George Town Owen Roberts Intl

Fri 26/2

2:55 p.m.-1:33 p.m.

1 stop22h 38m

C$ 425

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Wed 17/2

6:40 p.m.-1:45 p.m.

2 stops19h 05m

George Town Owen Roberts Intl

Tue 2/3

2:25 p.m.-9:55 a.m.

2 stops19h 30m

C$ 478

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Tue 24/11

3:45 p.m.-4:30 p.m.

1 stop24h 45m

George Town Owen Roberts Intl

Tue 1/12

5:45 p.m.-10:37 p.m.

1 stop28h 52m

C$ 489

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Sat 12/12

6:45 a.m.-1:45 p.m.

1 stop7h 00m

George Town Owen Roberts Intl

Sat 19/12

5:15 p.m.-9:15 p.m.

2 stops28h 00m

C$ 490

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Sat 2/1

9:44 a.m.-1:45 p.m.

2 stops28h 01m

George Town Owen Roberts Intl

Sat 9/1

5:45 p.m.-2:10 p.m.

1 stop20h 25m

C$ 490

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Sun 13/12

6:10 a.m.-4:30 p.m.

1 stop10h 20m

George Town Owen Roberts Intl

Mon 14/12

5:45 p.m.-6:45 p.m.

2 stops25h 00m

C$ 490

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Thu 3/12

3:35 p.m.-4:30 p.m.

2 stops24h 55m

George Town Owen Roberts Intl

Sun 13/12

5:45 p.m.-4:47 p.m.

2 stops23h 02m

C$ 490

TorontoGeorge Town

YYZ Toronto Pearson Intl - GCM George Town Owen Roberts Intl

YYZGCM

Toronto Pearson Intl

Sun 6/12

6:10 a.m.-4:30 p.m.

1 stop10h 20m

George Town Owen Roberts Intl

Tue 15/12

5:45 p.m.-10:37 p.m.

1 stop28h 52m

C$ 492

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/9

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Best time to book a flight to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight to the Cayman Islands

How long is the flight to Cayman Islands?

On average, a flight from Toronto to Cayman Islands takes 14 hours 51 minutes. Flights to Cayman Islands from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

What are the most popular airlines that fly to Cayman Islands?

The most popular airlines flying from Toronto to Cayman Islands are WestJet, Air Canada and Porter Airlines.

WestJet
WestJet
From C$ 338
Air Canada
Air Canada
From C$ 263
Porter Airlines
Porter Airlines
From C$ 348
United Airlines
United Airlines
From C$ 258

What are the cheapest airlines that fly to Cayman Islands?

The cheapest airlines flying from Toronto to Cayman Islands are American Airlines, Air Canada and WestJet.

When is the best time to book a flight to Cayman Islands?

To ensure you get the cheapest price possible for a flight to Cayman Islands, you should look to book at least 34 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What are the most popular places to fly to in Cayman Islands?

The most popular places in Cayman Islands to fly to are George Town, Cayman Brac and Little Cayman.

Reviews of airlines servicing Cayman Islands

Check out reviews from past customers who have flown Porter Airlines,United Airlines, andWestJet to the Cayman Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.4
Good
10,226 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
WestJet
7.2
Good
3,446 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,669 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
American Airlines
7.0
Good
12,077 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Food

7.6

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

FAQs about flying to Cayman Islands

Cayman Islands climate

The Cayman Islands has pleasant, beach-friendly temperatures all year round. The soothing trade winds keep the temperature from getting too hot. From May to November you’ll run into the rainy season, which also coincides with the hurricane season. 

What is good to know if travelling to Cayman Islands?

  • The islands feature some of the most spectacular diving areas the world over. Among these is the Bloody Bay Marine Park, which is located north of Little Cayman and remains a choice destination for divers.
  • Seven Mile Beach is the biggest one on Grand Cayman and features seemingly endless kilometres of shimmering white sand. Its downside is its popularity among the cruise-ship arrivals that sometimes makes for a crowded setting. As a result Rum Point may be a better option and is also good for children with changing areas, hammocks and a lively beach bar among the amenities.
  • Amateur sportsmen have much to occupy themselves with as the area features all of backpacking, hiking, kayaking, golfing and bird watching in plentiful supply throughout all three of the islands.
  • Grand Cayman is also known as Hell, something that is considerably more attractive than the name suggests. It is an area of often-spectacular black lava formations that also makes it an ideal setting for vacation pictures that are bound to stand out for years to come.
  • Beautiful beaches, palm trees gently swaying in the breeze and seemingly constant sunshine make the Cayman Islands a perfect setting for both weddings and honeymoons. If a beach wedding is not to your taste, chapel and church services are also on offer but remember to bring the necessary legal paperwork with you to make sure that your dream day goes off without a hitch – ahem.

  • When is the best time to fly to Cayman Islands?

    Peak Season: The most popular time for cheap flights to the Cayman Islands is between December and April. Off Season: Between May and November the rainy season prevails and can sometimes feature hurricanes so it is advisable to check the forecast before setting off. Some travellers consider the wet season to be the ideal time for finding cheap flights to the Cayman Islands. There are many possible reasons for this but chief among them are the cheaper hotel and resort rates, the uncrowded beaches and the fact that when the rain does arrive, it does so for relatively short periods.

  • Can I find cheaper flights to Cayman Islands if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Cayman Islands on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Cayman Islands?

    Based on reviews from Cheapflights users, American Airlines is rated the highest out of the airlines that fly to Cayman Islands.

  • What is the cheapest airport to fly to in Cayman Islands?

    George Town Owen Roberts Intl is currently the cheapest airport to fly to in Cayman Islands. One-way flights to George Town Owen Roberts Intl typically cost C$ 137, while round-trip flights cost around C$ 292.

  • How much is a round-trip flight to Cayman Islands?

    A round-trip flight to Cayman Islands will typically cost around C$ 389, however they can be found for as little as C$ 292.

  • Where does the fastest flight to Cayman Islands depart from?

    For those looking to save time traveling to Cayman Islands, Toronto offers the quickest one-way flight (4 hours 0 minutes).

  • Does George Town Owen Roberts Intl have rental cars?

    Yes. Those touching down at George Town Owen Roberts Intl can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to George Town Owen Roberts Intl?

    Yes. George Town Owen Roberts Intl has hotels nearby for those requiring accommodations. Centrally located, cozy studio in residential neighborhood. is the closest property to George Town Owen Roberts Intl (0.0 km away from George Town Owen Roberts Intl).

See more FAQs

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Find flights to Cayman Islands cities and airports

Flights to George Town
Flights to Cayman Brac
Flights to Little Cayman

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