$326 Find Cheap Flights from Bloomington to Caribbean Islands - Compare and Save

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Bloomington to Caribbean Islands departing on 9/3. 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 Bloomington 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 Bloomington to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Bloomington to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$362
Nassau
Nassau2 stops$720
Montego Bay
Montego Bay1 stop$362
Nassau
Nassau2 stops$720

Book Cheap Bloomington 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 Bloomington 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 Bloomington to Caribbean Islands

Thu, Sep 3 - Sun, Sep 6
American Airlines Logo
1:46 pm - 11:15 pm
BMI
-
SJU
8h 29m
1 stop
American Airlines Logo
6:00 am - 10:53 pm
SJU
-
BMI
17h 53m
2 stops
$326American Airlines
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
8:11 pm - 1:20 pm
BMI
-
MBJ
16h 09m
1 stop
American Airlines Logo
3:12 pm - 11:54 pm
MBJ
-
BMI
9h 42m
1 stop
$362American Airlines
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
8:11 pm - 3:53 pm
BMI
-
MBJ
18h 42m
2 stops
American Airlines Logo
2:02 pm - 10:50 am
MBJ
-
BMI
21h 48m
2 stops
$367American Airlines
Thu, Sep 3 - Sat, Sep 5
American Airlines Logo
1:46 pm - 11:15 pm
BMI
-
SJU
8h 29m
1 stop
American Airlines Logo
12:55 am - 1:00 pm
SJU
-
BMI
13h 05m
1 stop
$381American Airlines
Thu, Sep 3 - Sun, Sep 6
American Airlines Logo
4:49 pm - 9:43 am
BMI
-
SJU
15h 54m
2 stops
American Airlines Logo
6:00 am - 10:53 pm
SJU
-
BMI
17h 53m
2 stops
$431American Airlines
Sun, Oct 25 - Wed, Oct 28
United Airlines Logo
8:45 pm - 12:46 pm
BMI
-
MBJ
16h 01m
1 stop
United Airlines Logo
2:36 pm - 8:57 am
MBJ
-
BMI
18h 21m
2 stops
$472United Airlines
Sun, Oct 25 - Wed, Oct 28
United Airlines Logo
8:45 pm - 12:46 pm
BMI
-
MBJ
16h 01m
1 stop
United Airlines Logo
1:48 pm - 12:12 am
MBJ
-
BMI
10h 24m
1 stop
$477United Airlines
Sat, Jun 27 - Wed, Jul 8
Delta Logo
6:00 am - 4:40 pm
BMI
-
STT
9h 40m
1 stop
Delta Logo
1:21 pm - 10:48 pm
STT
-
BMI
10h 27m
1 stop
$747Delta
Tue, Jun 30 - Wed, Jul 8
Delta Logo
6:00 am - 3:21 pm
BMI
-
STT
8h 21m
1 stop
Delta Logo
3:33 pm - 10:48 pm
STT
-
BMI
8h 15m
1 stop
$847Delta
Mon, Nov 2 - Tue, Nov 17
WestJet Logo
12:00 pm - 4:33 pm
BMI
-
POP
26h 33m
2 stops
WestJet Logo
5:30 pm - 3:16 pm
POP
-
BMI
23h 46m
2 stops
$3,683WestJet
Booking Insights

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

Get data-powered insights and trends into flights from Bloomington 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 Bloomington 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 $324, prices are generally cheapest when you fly direct.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Bloomington 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 Bloomington to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Bloomington 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 Bloomington 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 Bloomington 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 Bloomington 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 Bloomington to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Bloomington to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Bloomington 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 Bloomington 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.
7.9
DeltaOverall score based on 8396 reviews
7.2Food
8.1Boarding
8.5Crew
7.8Comfort
7.8Entertainment
Airline reviews

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

2.0 MediocreBen, Jun 2026
ATL - HSV
Read more Delta reviews

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports