$568 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 1/18. 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 Town2 stops$568
Simpson Bay
Simpson Bay2 stops$569
George Town
George Town2 stops$568

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, Jan 18 - Sun, Jan 25
American Airlines Logo
6:00 pm - 11:26 am
MGM
-
GCM
16h 26m2 stops
American Airlines Logo
3:45 pm - 12:55 pm
GCM
-
MGM
22h 10m2 stops
$568American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
1:04 pm - 1:15 pm
MGM
-
SXM
23h 11m2 stops
American Airlines Logo
2:35 pm - 9:55 am
SXM
-
MGM
20h 20m2 stops
$569American Airlines
Sun, Jan 18 - Sun, Jan 25
American Airlines Logo
6:00 am - 11:26 am
MGM
-
GCM
28h 26m1 stop
American Airlines Logo
3:45 pm - 12:55 pm
GCM
-
MGM
22h 10m2 stops
$571American Airlines
Mon, Jan 19 - Mon, Jan 26
American Airlines Logo
6:00 am - 1:45 pm
MGM
-
SXM
29h 45m1 stop
American Airlines Logo
4:24 pm - 10:30 pm
SXM
-
MGM
8h 06m1 stop
$576American Airlines
Mon, Jan 19 - Mon, Jan 26
American Airlines Logo
5:44 pm - 2:31 pm
MGM
-
SXM
18h 47m2 stops
American Airlines Logo
4:24 pm - 12:54 pm
SXM
-
MGM
22h 30m2 stops
$578American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
5:45 am - 12:55 pm
MGM
-
SXM
6h 10m1 stop
American Airlines Logo
2:35 pm - 9:55 am
SXM
-
MGM
20h 20m2 stops
$592American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
5:45 am - 12:55 pm
MGM
-
SXM
6h 10m1 stop
American Airlines Logo
2:45 pm - 8:57 pm
SXM
-
MGM
7h 12m1 stop
$655American Airlines
Sun, Jan 18 - Sun, Jan 25
American Airlines Logo
2:03 pm - 11:26 am
MGM
-
GCM
20h 23m1 stop
American Airlines Logo
12:16 pm - 10:30 pm
GCM
-
MGM
11h 14m1 stop
$749American Airlines
Mon, Jan 26 - Thu, Jan 29
WestJet Logo
12:43 pm - 3:21 pm
MGM
-
SXM
24h 38m2 stops
WestJet Logo
4:20 pm - 10:38 pm
SXM
-
MGM
32h 18m2 stops
$3,599WestJet
Mon, Jan 26 - Thu, Jan 29
WestJet Logo
9:48 am - 3:21 pm
MGM
-
SXM
27h 33m2 stops
WestJet Logo
4:20 pm - 10:38 pm
SXM
-
MGM
32h 18m2 stops
$3,604WestJet
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 $469, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$568
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 George Town

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 11043 reviews
6.5Food
7.2Comfort
8.0Crew
7.5Boarding
6.9Entertainment
Airline reviews

Attendants were pleasant and the flight was smooth and relaxed.

10.0 ExcellentDawn C, Dec 2025
DFW - MIA
Read more American Airlines reviews

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports