Cheap Flights to Cayman Islands from NT$5,804

View NT$5,804 flight on Sat, 2026/11/21Opens in a new window

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Popular airlines to Cayman Islands

  • American Airlines

  • Delta

  • United

  • Air Canada

  • Southwest Airlines

  • Cayman Airways

  • JetBlue Airways

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How much is the cheapest flight to Cayman Islands?

Prices were available within the past 7 days and start at NT$5,804 for one-way flights and NT$14,742 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$14,742 Roundtrip, found 20 hours ago
NT$14,742
Roundtrip
found 20 hours ago
Select Air Canada flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$14,742 found 20 hours ago
Air Canada
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$15,058 Roundtrip, found 20 hours ago
NT$15,058
Roundtrip
found 20 hours ago
Select Air Canada flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$15,058 found 20 hours ago
Air Canada
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$17,316 Roundtrip, found 20 hours ago
NT$17,316
Roundtrip
found 20 hours ago
Select Air Canada flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$17,316 found 20 hours ago
Air Canada
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$21,983 Roundtrip, found 20 hours ago
NT$21,983
Roundtrip
found 20 hours ago
Select Air Canada flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$21,983 found 20 hours ago
Air Canada
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$22,091 Roundtrip, found 20 hours ago
NT$22,091
Roundtrip
found 20 hours ago
Select Air Canada flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$22,091 found 20 hours ago
United
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$24,038 Roundtrip, found 20 hours ago
NT$24,038
Roundtrip
found 20 hours ago
Select United flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$24,038 found 20 hours ago
United
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$24,197 Roundtrip, found 20 hours ago
NT$24,197
Roundtrip
found 20 hours ago
Select United flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$24,197 found 20 hours ago
American Airlines
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$24,373 Roundtrip, found 20 hours ago
NT$24,373
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$24,373 found 20 hours ago
American Airlines
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$24,532 Roundtrip, found 20 hours ago
NT$24,532
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$24,532 found 20 hours ago
Delta
Sat, Nov 21 - Fri, Nov 27
ORD
Chicago
GCM
Grand Cayman
NT$54,443 Roundtrip, found 20 hours ago
NT$54,443
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Nov 21 from Chicago to Grand Cayman, returning Fri, Nov 27, priced at NT$54,443 found 20 hours 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, NT$14,742 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 Chicago (ORD), you could've picked up a cheap seat for just NT$5,804 in the last seven days. Return flights to Cayman Islands ranged from only NT$14,742 to NT$54,443 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 vacationers preferring to take off on the weekend.
How much is a plane ticket to Cayman Islands?
Fares ranged from NT$14,742 to NT$54,443 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 85ºF to 85ºF. 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.

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