Where can I fly from to get the cheapest fares to Little Cayman?

Based on fares booked in the past 5 days, the cheapest flights to Little Cayman are from: • New York, from $698 round-trip

How do I know if a flight to Little Cayman is a good deal?

A good deal on a flight to Little Cayman is around $498 round-trip. This fare is in the lowest 25% of round-trip prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

$404 CHEAP FLIGHTS to Little Cayman in 2026/27

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Cheapest round-trip

$404

Typical prices: $498-$1,055

Cayman Airways

Wed 12/12Fri 12/14

MIA - LYB • 1 stop

When to travel

May

Cheapest • 18% price drop

June

Most popular

Good to know

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We hope you love your trip to Little Cayman!

Flight Deals

Cheap Flights to Little Cayman

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

All Flight Deals

Recent round-trip flight deals to Little Cayman

Sat, Dec 12 - Mon, Dec 14

11:50 am - 3:35 pmMIA Miami-LYB Little Cayman

3h 45m1 stop Cayman Brac Gerrard-Smith

3:15 pm - 1:05 pmLYB Little Cayman-MIA Miami

21h 50m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$404Cayman Airways

Sat, Dec 12 - Mon, Dec 14

11:50 am - 8:35 amMIA Miami-LYB Little Cayman

20h 45m1 stop Cayman Brac Gerrard-Smith

4:00 pm - 1:05 pmLYB Little Cayman-MIA Miami

21h 05m1 stop George Town Owen Roberts Intl

$429Cayman Airways

Sat, Dec 12 - Mon, Dec 14

11:50 am - 7:40 amMIA Miami-LYB Little Cayman

19h 50m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

3:15 pm - 1:05 pmLYB Little Cayman-MIA Miami

21h 50m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$435Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 7:40 amTPA Tampa-LYB Little Cayman

17h 25m1 stop George Town Owen Roberts Intl

8:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

5h 40m1 stop George Town Owen Roberts Intl

$451Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 10:45 amTPA Tampa-LYB Little Cayman

20h 30m1 stop George Town Owen Roberts Intl

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$475Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 10:10 amTPA Tampa-LYB Little Cayman

19h 55m1 stop George Town Owen Roberts Intl

8:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

5h 40m1 stop George Town Owen Roberts Intl

$479Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 8:35 amTPA Tampa-LYB Little Cayman

18h 20m2 stops George Town Owen Roberts Intl Cayman Brac Gerrard-Smith

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$481Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 7:40 amTPA Tampa-LYB Little Cayman

17h 25m1 stop George Town Owen Roberts Intl

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$515Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 3:35 pmTPA Tampa-LYB Little Cayman

25h 20m2 stops George Town Owen Roberts Intl Cayman Brac Gerrard-Smith

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$521Cayman Airways

Fri, Nov 27 - Mon, Nov 30

6:55 pm - 3:55 pmLGA New York LaGuardia-LYB Little Cayman

21h 00m2 stops Toronto Pearson Intl George Town Owen Roberts Intl

4:00 pm - 10:53 amLYB Little Cayman-LGA New York LaGuardia

42h 53m2 stops George Town Owen Roberts Intl Toronto Pearson Intl

$698Multiple Airlines

All round-trip flight deals to Little Cayman

Sat, Dec 12 - Mon, Dec 14

11:50 am - 3:35 pmMIA Miami-LYB Little Cayman

3h 45m1 stop Cayman Brac Gerrard-Smith

3:15 pm - 1:05 pmLYB Little Cayman-MIA Miami

21h 50m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$404Cayman Airways

Sat, Dec 12 - Mon, Dec 14

11:50 am - 8:35 amMIA Miami-LYB Little Cayman

20h 45m1 stop Cayman Brac Gerrard-Smith

4:00 pm - 1:05 pmLYB Little Cayman-MIA Miami

21h 05m1 stop George Town Owen Roberts Intl

$429Cayman Airways

Sat, Dec 12 - Mon, Dec 14

11:50 am - 7:40 amMIA Miami-LYB Little Cayman

19h 50m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

3:15 pm - 1:05 pmLYB Little Cayman-MIA Miami

21h 50m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$435Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 7:40 amTPA Tampa-LYB Little Cayman

17h 25m1 stop George Town Owen Roberts Intl

8:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

5h 40m1 stop George Town Owen Roberts Intl

$451Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 10:45 amTPA Tampa-LYB Little Cayman

20h 30m1 stop George Town Owen Roberts Intl

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$475Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 10:10 amTPA Tampa-LYB Little Cayman

19h 55m1 stop George Town Owen Roberts Intl

8:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

5h 40m1 stop George Town Owen Roberts Intl

$479Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 8:35 amTPA Tampa-LYB Little Cayman

18h 20m2 stops George Town Owen Roberts Intl Cayman Brac Gerrard-Smith

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$481Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 7:40 amTPA Tampa-LYB Little Cayman

17h 25m1 stop George Town Owen Roberts Intl

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$515Cayman Airways

Fri, Oct 30 - Mon, Nov 2

3:15 pm - 3:35 pmTPA Tampa-LYB Little Cayman

25h 20m2 stops George Town Owen Roberts Intl Cayman Brac Gerrard-Smith

7:50 am - 2:30 pmLYB Little Cayman-TPA Tampa

6h 40m2 stops Cayman Brac Gerrard-Smith George Town Owen Roberts Intl

$521Cayman Airways

Fri, Nov 27 - Mon, Nov 30

6:55 pm - 3:55 pmLGA New York LaGuardia-LYB Little Cayman

21h 00m2 stops Toronto Pearson Intl George Town Owen Roberts Intl

4:00 pm - 10:53 amLYB Little Cayman-LGA New York LaGuardia

42h 53m2 stops George Town Owen Roberts Intl Toronto Pearson Intl

$698Multiple Airlines

Booking Insights

Price, demand and travel trends for United States to Little Cayman flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from the United States to Little Cayman with more confidence.

What is the cheapest time of day to fly to Little Cayman?

Afternoon flights to Little Cayman are the cheapest at $501 round-trip on average. Evening flights are the most expensive at $1,106.

Find deals

Low season	January
High season	June
Cheapest flight	$404

Flight from Miami to Little Cayman

When to book flights to Little Cayman

Are your dates flexible? Find out the best times to travel to Little Cayman based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated round-trip price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Little Cayman based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

How do I know if a flight to Little Cayman is a good deal?
A good deal on a flight to Little Cayman is around $498 round-trip. This fare is in the lowest 25% of round-trip prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.
Where can I fly from to get the cheapest fares to Little Cayman?
Based on fares booked in the past 5 days, the cheapest flights to Little Cayman are from:
• New York, from $698 round-trip

For flights to Little Cayman, recent KAYAK data shows that stronger deals tend to land around $498 round-trip. If you see a fare below that threshold, it's a strong deal – book before the price climbs back up.
If you can choose when to go, time your trip to Little Cayman around May. Round-trip fares historically average $427 that month – typically the cheapest month to travel based on the last 12 months.
Before you book:

• Check the route's typical price range so you can spot a deal.
• Confirm baggage fees and seat-selection costs on budget carriers.
• Verify whether you need any travel documents beyond ID.
• Pick a departure airport, since your nearest may not be the cheapest origin.
Shift your departure to noon to save up to $605 per round-trip. Noon flights to Little Cayman average $501 compared to $1,106 for afternoon flights. See the time-of-day chart above for the full breakdown.