$109 Find Cheap Flights from Caribbean Islands to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 4/20. 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 Caribbean Islands to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Chicago 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 Caribbean Islands to Chicago

Thu, May 21 - Sat, May 23
Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:59 am - 6:56 am
ORD
-
SJU
4h 57mnonstop
$128Frontier
Thu, May 21 - Tue, May 26
Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
Frontier Logo
1:15 pm - 11:26 pm
ORD
-
SJU
9h 11m
1 stop
$182Frontier
Tue, Mar 17 - Wed, Apr 8
Multiple Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
Multiple Airlines Logo
4:21 pm - 2:01 am
ORD
-
SJU
8h 40m
1 stop
$205Multiple Airlines
Mon, Mar 16 - Tue, Mar 24
Multiple Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
Multiple Airlines Logo
4:18 pm - 8:54 am
ORD
-
SJU
15h 36m
1 stop
$210Multiple Airlines
Thu, Apr 16 - Wed, Apr 22
Delta Logo
6:15 am - 12:07 pm
SJU
-
MDW
6h 52m
1 stop
Delta Logo
12:52 pm - 11:12 pm
MDW
-
SJU
9h 20m
1 stop
$246Delta
Tue, Mar 17 - Sun, Mar 22
United Airlines Logo
1:55 pm - 6:08 pm
PUJ
-
ORD
5h 13mnonstop
United Airlines Logo
6:00 am - 4:25 pm
ORD
-
PUJ
9h 25m
1 stop
$275United Airlines
Wed, Apr 22 - Wed, May 6
United Airlines Logo
3:35 pm - 7:26 am
PUJ
-
ORD
16h 51m
1 stop
United Airlines Logo
5:00 am - 1:11 pm
ORD
-
PUJ
7h 11m
1 stop
$280United Airlines
Fri, May 1 - Wed, May 6
American Airlines Logo
12:06 pm - 4:25 pm
PUJ
-
ORD
5h 19mnonstop
American Airlines Logo
5:00 am - 4:25 pm
ORD
-
PUJ
10h 25m
1 stop
$283American Airlines
Fri, May 1 - Tue, May 5
American Airlines Logo
3:50 pm - 7:39 am
PUJ
-
ORD
16h 49m
1 stop
American Airlines Logo
8:46 pm - 12:39 pm
ORD
-
PUJ
14h 53m
1 stop
$293American Airlines
Wed, Apr 1 - Tue, Apr 7
Delta Logo
6:10 pm - 10:31 pm
NAS
-
MDW
5h 21m
1 stop
Delta Logo
6:00 am - 4:45 pm
MDW
-
NAS
9h 45m
1 stop
$465Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs for booking flights from Caribbean Islands to Chicago

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

    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 Caribbean Islands to Chicago.

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

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

    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 to Chicago with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Chicago?

    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 to Chicago from 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 3 airlines serving from Caribbean Islands to Chicago

 
Need help choosing which airline to fly with from Caribbean Islands to Chicago? 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 8245 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

8.0 ExcellentSharon, Feb 2026
CVG - ATL
Read more Delta reviews

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Improve boarding- the zone assignment and boarding is always a mess- there is not clear instructions of what is going on at the gate. As a meme bet there is no more selection of a good seats when booking. Only offers middle seats to choose or pay extra. There is not more benefit with Amex no benefits at all.

alike schedule and times it’s very good for me, I will stay wad delta for ever

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Flight from CHI to PVD was delayed by over 20 hours.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint Joseph
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Valparaiso
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Schererville
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Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Caribbean Islands

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.