$332 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 5/3. 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

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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$387
Nassau
Nassau2 stops$585
Montego Bay
Montego Bay2 stops$387
Nassau
Nassau2 stops$585

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

Sun, May 3 - Fri, May 8
American Airlines Logo
5:00 am - 9:15 pm
BMI
-
SJU
15h 15m
2 stops
American Airlines Logo
11:59 pm - 3:15 pm
SJU
-
BMI
16h 16m
1 stop
$332American Airlines
Sun, May 3 - Fri, May 8
American Airlines Logo
5:00 am - 9:15 pm
BMI
-
SJU
15h 15m
2 stops
American Airlines Logo
7:25 am - 11:52 pm
SJU
-
BMI
17h 27m
2 stops
$378American Airlines
Thu, May 28 - Mon, Jun 1
American Airlines Logo
4:22 pm - 11:45 am
BMI
-
MBJ
19h 23m
2 stops
American Airlines Logo
5:17 pm - 3:52 pm
MBJ
-
BMI
22h 35m
2 stops
$387American Airlines
Thu, May 28 - Mon, Jun 1
American Airlines Logo
4:22 pm - 11:45 am
BMI
-
MBJ
19h 23m
2 stops
American Airlines Logo
2:23 pm - 11:59 pm
MBJ
-
BMI
9h 36m
1 stop
$436American Airlines
Mon, Mar 23 - Wed, Apr 1
Delta Logo
4:04 pm - 11:15 pm
BMI
-
SJU
6h 11m
1 stop
Delta Logo
6:15 am - 3:23 pm
SJU
-
BMI
10h 08m
1 stop
$438Delta
Thu, May 28 - Mon, Jun 1
American Airlines Logo
4:22 pm - 11:19 am
BMI
-
MBJ
18h 57m
2 stops
American Airlines Logo
2:23 pm - 11:01 am
MBJ
-
BMI
20h 38m
1 stop
$442American Airlines
Fri, May 1 - Tue, May 5
American Airlines Logo
3:45 pm - 11:33 am
BMI
-
GCM
19h 48m
2 stops
American Airlines Logo
12:35 pm - 11:52 pm
GCM
-
BMI
11h 17m
2 stops
$474American Airlines
Thu, Mar 26 - Wed, Apr 1
Delta Logo
12:02 pm - 11:15 pm
BMI
-
SJU
10h 13m
1 stop
Delta Logo
2:44 pm - 10:19 pm
SJU
-
BMI
8h 35m
1 stop
$500Delta
Wed, Mar 18 - Mon, Mar 30
Delta Logo
4:04 pm - 11:15 pm
BMI
-
SJU
6h 11m
1 stop
Delta Logo
6:15 am - 3:23 pm
SJU
-
BMI
10h 08m
1 stop
$520Delta
Mon, Mar 2 - Thu, Mar 5
WestJet Logo
3:36 pm - 5:17 pm
BMI
-
NAS
48h 41m
2 stops
WestJet Logo
11:20 am - 2:51 pm
NAS
-
BMI
28h 31m
2 stops
$1,696WestJet
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 American Airlines ($332) and Delta ($438).

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 8215 reviews
7.9Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

2.0 MediocreCason, Feb 2026
EWR - ATL
Read more Delta reviews

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

This is my worse experience with Delta. My colleagues and I were traveling to ICT for work. Usually we connect in Dallas, but this year we decided to book with Delta and connect in Atlanta. We were excited to fly with Delta because we hear great things and Delta is one of my top choices when choosing an airline for travel. On the connecting flights to and from Wichita/Atlanta - it felt hot and uncomfortable on the plane. The plane to ICT was smaller and older and did not have any wi-fi or entertainment. The most terrible experience was at boarding in Atlanta both times traveling to Wichita and then back to Tampa. First on our flight from ATL to ICT - the attendant scanning our boarding pass made us go back to the line when we went up to scan our passes to wait. After a few minutes, she allowed us to come back up to scan but then she asked what boarding zone we were. We told her zone 5, and since we were standing on the wrong side of the small rope partition, she made us go back to stand on the right side. There was another gentleman that came up to board and scan his pass, and she mentioned he was also on the wrong side but she let him go through. Our group had to walk back and forth for no reason, causing an unnecessary delay to board the plane. We have never experienced anything like this, especially when the boarding area was completely empty and everyone already boarded since boarding was earlier than the original boarding time. On our flight from ATL to TPA, the attendants scanning our boarding passes had us scan our passes twice, not explaining to us what was going on. They automatically started tagging our carry on bags and did not explain to us or tell us what was going on and why this was happening. Obviously we knew our bags were being forced to check in but with no reason. There was no announcement or mention and I have never had anyone force me to check in my bag before boarding the plane. We assumed the overhead bins were full but when we boarded the plane, there was a lot of empty bins and a lot of spaces to put our bags. We all were disappointed and frustrated with Delta and will be hesitant to fly Delta again or anytime soon.

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

It was good. The leg room was not great in Row 1.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports