$275 Find Cheap Flights from Bloomington 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 Bloomington to Caribbean Islands departing on 12/8. 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

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$573
Montego Bay
Montego Bay1 stop$573

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

Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
4:55 pm - 1:45 pmBMI-SJU
18h 50m2 stops
American Airlines Logo
4:45 pm - 2:30 pmSJU-BMI
23h 45m2 stops
$275American Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
6:14 am - 2:40 pmBMI-SJU
6h 26m1 stop
American Airlines Logo
9:30 am - 3:41 pmSJU-BMI
8h 11m2 stops
$415American Airlines
Find Deal
Fri, Nov 28 - Sat, Dec 6
American Airlines Logo
11:10 am - 2:10 amBMI-SJU
13h 00m2 stops
American Airlines Logo
5:50 am - 9:20 pmSJU-BMI
17h 30m2 stops
$425American Airlines
Find Deal
Wed, Dec 31 - Thu, Jan 8
Delta Logo
6:00 am - 4:00 pmBMI-STT
8h 00m1 stop
Delta Logo
4:00 pm - 10:26 pmSTT-BMI
8h 26m1 stop
$549Delta
Find Deal
Tue, Sep 30 - Wed, Oct 1
Delta Logo
6:05 am - 1:33 pmBMI-STT
6h 28m1 stop
Delta Logo
2:43 pm - 10:11 pmSTT-BMI
8h 28m1 stop
$589Delta
Find Deal
Sat, Jan 24 - Tue, Feb 10
Delta Logo
6:01 am - 3:54 pmBMI-STT
7h 53m1 stop
Delta Logo
3:00 pm - 10:26 pmSTT-BMI
9h 26m1 stop
$694Delta
Find Deal
Tue, Jan 27 - Thu, Feb 26
Delta Logo
6:01 am - 3:54 pmBMI-STT
7h 53m1 stop
Delta Logo
3:00 pm - 10:26 pmSTT-BMI
9h 26m1 stop
$839Delta
Find Deal
Sun, Sep 14 - Sun, Sep 21
WestJet Logo
3:39 pm - 9:26 amBMI-MBJ
17h 47m2 stops
WestJet Logo
1:40 pm - 10:11 pmMBJ-BMI
32h 31m2 stops
$3,389WestJet
Find Deal
Sun, Aug 10 - Sun, Aug 24
WestJet Logo
4:10 pm - 9:27 amBMI-MBJ
17h 17m2 stops
WestJet Logo
1:40 pm - 3:07 pmMBJ-BMI
49h 27m2 stops
$3,453WestJet
Find Deal
Thu, Aug 14 - Sun, Aug 17
WestJet Logo
3:47 pm - 9:27 amBMI-MBJ
17h 40m2 stops
WestJet Logo
1:40 pm - 3:07 pmMBJ-BMI
49h 27m2 stops
$3,488WestJet
Find Deal
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 $423, prices are generally cheapest when you fly direct.


Good to know

Low seasonSeptember
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 36% lower on average.

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.

  • 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 $664 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $664.

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.
8.0
DeltaOverall score based on 7980 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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