$366 Find Cheap Flights from Bloomington to Caribbean

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 departing on 10/27. 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

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Cheap Flights from Bloomington to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay2 stops$482
Nassau
Nassau2 stops$570
Montego Bay
Montego Bay2 stops$482
Nassau
Nassau2 stops$570

Book Cheap Bloomington to Caribbean 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 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

Tue, Oct 27 - Wed, Oct 28
United Airlines Logo
9:44 am - 11:36 pm
BMI
-
SJU
12h 52m
2 stops
United Airlines Logo
1:05 am - 12:50 pm
SJU
-
BMI
12h 45m
2 stops
$366United Airlines
Sun, Aug 30 - Sat, Sep 5
American Airlines Logo
5:00 am - 3:01 pm
BMI
-
STT
9h 01m
2 stops
American Airlines Logo
4:42 pm - 1:06 pm
STT
-
BMI
21h 24m
2 stops
$445American Airlines
Mon, Oct 26 - Thu, Oct 29
United Airlines Logo
9:44 am - 1:29 pm
BMI
-
MBJ
27h 45m
2 stops
United Airlines Logo
2:36 pm - 8:57 am
MBJ
-
BMI
18h 21m
2 stops
$482United Airlines
Sun, Aug 30 - Sat, Sep 5
Delta Logo
6:00 am - 1:34 pm
BMI
-
STT
6h 34m
1 stop
Delta Logo
4:10 pm - 10:22 pm
STT
-
BMI
7h 12m
1 stop
$489Delta
Mon, Aug 31 - Sun, Sep 6
American Airlines Logo
5:00 am - 2:59 pm
BMI
-
STT
8h 59m
2 stops
American Airlines Logo
1:49 pm - 1:06 pm
STT
-
BMI
24h 17m
2 stops
$525American Airlines
Mon, Oct 26 - Thu, Oct 29
United Airlines Logo
6:00 am - 12:46 pm
BMI
-
MBJ
6h 46m
1 stop
United Airlines Logo
1:48 pm - 12:12 am
MBJ
-
BMI
10h 24m
1 stop
$535United Airlines
Tue, Jun 30 - Tue, Jul 7
American Airlines Logo
6:02 pm - 1:08 pm
BMI
-
MBJ
19h 06m
2 stops
American Airlines Logo
5:14 pm - 5:34 pm
MBJ
-
BMI
24h 20m
2 stops
$539American Airlines
Mon, Aug 31 - Sun, Sep 6
Delta Logo
6:01 am - 1:52 pm
BMI
-
STT
6h 51m
1 stop
Delta Logo
3:02 pm - 10:22 pm
STT
-
BMI
8h 20m
1 stop
$542Delta
Sat, Aug 29 - Wed, Sep 2
WestJet Logo
6:00 am - 11:10 am
BMI
-
NAS
28h 10m
2 stops
WestJet Logo
12:00 pm - 3:15 pm
NAS
-
BMI
28h 15m
2 stops
$3,523WestJet
Sat, Aug 29 - Wed, Sep 2
WestJet Logo
6:00 am - 11:10 am
BMI
-
NAS
28h 10m
2 stops
WestJet Logo
12:00 pm - 3:15 pm
NAS
-
BMI
28h 15m
2 stops
$3,525WestJet
Booking Insights

KAYAK's insights & trends for Bloomington to Caribbean flights

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

Which airlines provide the cheapest flights from Bloomington to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Bloomington to Caribbean were found on United Airlines ($366) and American Airlines ($445).

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Bloomington to Caribbean 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?

    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 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?

    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 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

 
Need help choosing which airline to fly with from Bloomington to Caribbean? 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 8454 reviews
7.8Comfort
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

10.0 Excellentangela, May 2026
LGA - PBI
Read more Delta reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

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

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports