Flight to Cayman Islands

View S$231 flight on Fri, 6 Feb, 2026Opens in a new window

Popular airlines to Cayman Islands

  • American Airlines

    American Airlines

  • Delta

    Delta

  • Air Canada

    Air Canada

  • United

    United

  • Southwest Airlines

    Southwest Airlines

  • JetBlue Airways

    JetBlue Airways

  • Spirit Airlines

    Spirit Airlines

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap round-trip flights to Cayman Islands

Prices were available within the past 7 days and start at S$231 for one-way flights and S$636 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$636 Return, found 1 day ago
S$636
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$636 found 1 day ago
United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$641 Return, found 1 day ago
S$641
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$641 found 1 day ago
United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$660 Return, found 1 day ago
S$660
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$660 found 1 day ago
United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$665 Return, found 1 day ago
S$665
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$665 found 1 day ago
United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$667 Return, found 1 day ago
S$667
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$667 found 1 day ago
Air Canada
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$671 Return, found 1 day ago
S$671
Return
found 1 day ago
Select Air Canada flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$671 found 1 day ago
United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$672 Return, found 1 day ago
S$672
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$672 found 1 day ago
Air Canada
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$675 Return, found 1 day ago
S$675
Return
found 1 day ago
Select Air Canada flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$675 found 1 day ago
United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$696 Return, found 1 day ago
S$696
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$696 found 1 day ago
United
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$700 Return, found 1 day ago
S$700
Return
found 1 day ago
Select United flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$700 found 1 day ago
American Airlines
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$729 Return, found 1 day ago
S$729
Return
found 1 day ago
Select American Airlines flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$729 found 1 day ago
WestJet
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$740 Return, found 1 day ago
S$740
Return
found 1 day ago
Select WestJet flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$740 found 1 day ago
Delta
Fri, 6 Feb - Tue, 10 Feb
YYC
Calgary
GCM
Grand Cayman
S$1,663 Return, found 1 day ago
S$1,663
Return
found 1 day ago
Select Delta flight, departing Fri, 6 Feb from Calgary to Grand Cayman, returning Tue, 10 Feb, priced at S$1,663 found 1 day ago

Frequently asked questions

How do I find cheap flights to Cayman Islands that have flexible change policies?
Search for your affordable fares to Cayman Islands, then mark the "No change fee" box directly below the "Flexible change policies" heading. It's that simple. We appreciate that travel plans can change and flexibility is essential, so you can book with confidence with Expedia.
Which airlines fly to Cayman Islands?
Find your passport, pack your bags and choose between these leading airlines that service Cayman Islands:

  • American Airlines - 130 flights to or near Cayman Islands each month, including 130 flights to Owen Roberts Intl. Airport (GCM) per month.
  • Cayman Airways - 82 flights to or near Cayman Islands each month, including 78 flights to Owen Roberts Intl. Airport (GCM) per month.
  • United Airlines - 47 flights to or near Cayman Islands each month, including 47 flights to Owen Roberts Intl. Airport (GCM) per month.

How can I find cheap tickets to Cayman Islands?
In the last seven days, S$636 was the best price for a flight to Cayman Islands. For even bigger savings, book well in advance and be flexible with your travel dates. Search for your trip to Cayman Islands, then compare prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Cayman Islands?
If you were journeying one way from Calgary (YYC), you could've picked up a cheap seat for just S$231 in the last seven days. Return flights to Cayman Islands ranged from only S$636 to S$1,663 during this same period.
What are the most popular airports to fly into in Cayman Islands?
Pack your suitcase and cruise into one of these top Cayman Islands airports:

  • Owen Roberts Intl. Airport (GCM) - 338 flights per month.
  • Gerrard Smith Intl. Airport (CYB) - 4 flights per month.

When is the cheapest time to fly to Cayman Islands?
If you're not fixed on what day you travel to Cayman Islands, fly out early in the week. The cheapest day to take off is generally Tuesday, closely followed by Monday. Saturday is typically the priciest day, with lots of holiday makers preferring to take off on the weekend.
How much is a plane ticket to Cayman Islands?
Fares ranged from S$636 to S$1,663 over the last seven days. When you're ready to book, we'll help you secure the best price to Cayman Islands.
What is the best time to go to Cayman Islands?
George Town, Cayman Islands's most populated city, is an awesome place to check out at anytime. Not into cold weather? Then journey here from June 20 onward in summer, when average temperatures range from 29ºC to 29ºC. July, August and October is when George Town draws the biggest crowds.
What months are the cheapest to book a flight to Cayman Islands?
An inexpensive month to book an awesome deal to Cayman Islands is February, while prices are at their highest in December. Give this month a miss if you're on a budget.

Book with confidence

Expedia offers flights to Cayman Islands to meet every traveller's needs. Whatever your flight need - Expedia has the flight for you. So choose from flights to Cayman Islands or destinations around the world and discover how easy it is to make your flight reservations on Expedia.

Travel information

Cayman Islands Flights Information

Airlines serving
United, American Airlines, WestJet, Air Canada, Delta
Roundtrip price
from S$636
Cayman Islands Flights Information

Explore a world of travel with Expedia

*Available to Expedia members.