$551 Find Cheap Flights from Montgomery to Caribbean Islands

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montgomery to Caribbean Islands departing on 2/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montgomery to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montgomery to Caribbean Islands, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Montgomery to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Simpson Bay
Simpson Bay2 stops$569
George Town
George Town1 stop$877
Simpson Bay
Simpson Bay2 stops$569
George Town
George Town1 stop$877

Book Cheap Montgomery to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montgomery to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Montgomery to Caribbean Islands

Sun, Feb 15 - Thu, Feb 19
American Airlines Logo
5:45 pm - 11:10 am
MGM
-
GGT
16h 25m2 stops
American Airlines Logo
1:30 pm - 11:52 pm
GGT
-
MGM
11h 22m1 stop
$551American Airlines
Mon, Feb 9 - Thu, Feb 19
American Airlines Logo
6:00 am - 1:19 pm
MGM
-
GGT
6h 19m1 stop
American Airlines Logo
1:30 pm - 11:52 pm
GGT
-
MGM
11h 22m1 stop
$562American Airlines
Mon, Feb 9 - Wed, Feb 18
American Airlines Logo
5:44 pm - 2:10 pm
MGM
-
GGT
19h 26m2 stops
American Airlines Logo
11:50 am - 11:16 pm
GGT
-
MGM
12h 26m2 stops
$567American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
5:44 pm - 3:20 pm
MGM
-
SXM
20h 36m2 stops
American Airlines Logo
4:05 pm - 9:55 am
SXM
-
MGM
18h 50m2 stops
$569American Airlines
Mon, Feb 9 - Mon, Feb 16
American Airlines Logo
6:00 am - 1:19 pm
MGM
-
GGT
6h 19m1 stop
American Airlines Logo
1:30 pm - 11:52 pm
GGT
-
MGM
11h 22m1 stop
$587American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
5:45 am - 12:55 pm
MGM
-
SXM
6h 10m1 stop
American Airlines Logo
4:05 pm - 5:42 pm
SXM
-
MGM
26h 37m2 stops
$592American Airlines
Mon, Feb 9 - Mon, Feb 16
American Airlines Logo
6:00 pm - 11:26 am
MGM
-
GGT
16h 26m2 stops
American Airlines Logo
1:30 pm - 11:52 pm
GGT
-
MGM
11h 22m1 stop
$592American Airlines
Sun, May 10 - Wed, May 13
United Airlines Logo
1:00 pm - 12:31 pm
MGM
-
GCM
23h 31m1 stop
United Airlines Logo
1:35 pm - 4:22 pm
GCM
-
MGM
26h 47m1 stop
$877United Airlines
Sun, Feb 8 - Wed, Feb 11
WestJet Logo
12:47 pm - 3:17 pm
MGM
-
SXM
24h 30m2 stops
WestJet Logo
4:20 pm - 5:43 pm
SXM
-
MGM
27h 23m2 stops
$3,806WestJet
Sun, Feb 8 - Wed, Feb 11
WestJet Logo
12:47 pm - 3:17 pm
MGM
-
SXM
24h 30m2 stops
WestJet Logo
4:20 pm - 10:41 pm
SXM
-
MGM
32h 21m2 stops
$3,821WestJet
Booking Insights

KAYAK's insights & trends for Montgomery to Caribbean Islands flights

Get data-powered insights and trends into flights from Montgomery to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Montgomery to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $455, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$551
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Montgomery to Georgetown

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Montgomery to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Montgomery to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Montgomery to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Montgomery to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Montgomery to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Montgomery to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Montgomery to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Montgomery to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $510 on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $661.

Reviews of the top airline flying from Montgomery to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Montgomery to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Montgomery to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11062 reviews
8.0Crew
6.9Entertainment
6.5Food
7.5Boarding
7.2Comfort
Airline reviews

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

2.0 MediocreBrandyi, Dec 2025
LAX - HND
Read more American Airlines reviews

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports