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$100 Find cheap flights from Caribbean to Chicago O'Hare Intl Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 5/4. 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
0 bags
Mon 5/27
Mon 6/3

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Good to know

Low season

January

High season

November

Cheapest flight

$100
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Punta Cana to Chicago O'Hare Airport

FAQs for booking Caribbean to Chicago O'Hare Airport flights

  • How does KAYAK find such low prices on flights from Caribbean to Chicago O'Hare Airport?

    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 to Chicago O'Hare Airport.

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

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

    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 O'Hare Airport with an airline and back to Caribbean with another airline.

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

    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 O'Hare Airport from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Caribbean to Chicago O'Hare Airport?

Find which airlines fly direct from Caribbean to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Caribbean to Chicago O'Hare Intl

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Caribbean

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

See more direct flights
See more direct flights

Top 5 airlines serving from Caribbean to O'Hare Intl

 
Need help choosing which airline to fly with from Caribbean to O'Hare Intl? 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 10951 reviews
8.6crew
7.4food
8.2boarding
7.9comfort
8.0entertainment
Airline reviews

The pilots were good. Disappointing when planes don't have electrical ports

6.0 GoodAnonymous, Apr 2024ATL - CHS
Read more about Delta reviews

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Caribbean to Chicago

Recent round-trip flight deals

5/10Fri
1 stopSpirit Airlines
13h 55mSJU-ORD
5/13Mon
1 stopSpirit Airlines
14h 16mORD-SJU
$179
5/7Tue
nonstopSpirit Airlines
5h 19mSJU-ORD
5/9Thu
nonstopSpirit Airlines
4h 53mORD-SJU
$180
5/3Fri
1 stopFrontier
21h 34mSJU-ORD
5/12Sun
1 stopFrontier
12h 52mORD-SJU
$196
5/3Fri
1 stopFrontier
21h 34mSJU-ORD
5/8Wed
1 stopFrontier
14h 25mORD-SJU
$215
5/3Fri
1 stopAmerican Airlines
7h 02mSJU-ORD
5/6Mon
1 stopAmerican Airlines
9h 35mORD-SJU
$221
5/6Mon
1 stopAmerican Airlines
11h 25mSJU-ORD
5/12Sun
1 stopAmerican Airlines
8h 35mORD-SJU
$225
7/4Thu
nonstopUnited Airlines
4h 59mPUJ-ORD
7/15Mon
nonstopUnited Airlines
4h 36mORD-PUJ
$377
10/23Wed
1 stopUnited Airlines
7h 39mPUJ-ORD
10/27Sun
nonstopUnited Airlines
4h 30mORD-PUJ
$387
5/15Wed
2 stopsDelta
14h 41mMBJ-ORD
9/2Mon
2 stopsDelta
16h 01mORD-MBJ
$423
6/25Tue
1 stopDelta
14h 25mSDQ-ORD
9/4Wed
1 stopDelta
14h 40mORD-SDQ
$441

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Recent one-way flight deals

5/4Sat
nonstopFrontier
5h 21mPUJ-ORD
$100
5/17Fri
1 stopSpirit Airlines
8h 14mSTT-ORD
$106
5/3Fri
1 stopAmerican Airlines
17h 20mSJU-ORD
$111
5/6Mon
1 stopAmerican Airlines
11h 25mSJU-ORD
$112
5/2Thu
1 stopUnited Airlines
10h 35mSJU-ORD
$178
5/5Sun
nonstopUnited Airlines
4h 59mPUJ-ORD
$201
5/11Sat
2 stopsDelta
19h 50mSDQ-ORD
$202
9/19Thu
1 stopDelta
16h 59mPUJ-ORD
$248
5/6Mon
1 stopJetBlue
14h 46mSDQ-ORD
$282
5/10Fri
1 stopJetBlue
14h 46mSDQ-ORD
$283

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Last minute flights from Caribbean to O'Hare Intl

Last minute flight, train and bus deals

5/2Thu
nonstopSpirit Airlines
5h 19mSJU-ORD
5/5Sun
nonstopSpirit Airlines
4h 43mORD-SJU
$176
5/1Wed
nonstopFrontier
5h 29mPUJ-ORD
5/5Sun
nonstopFrontier
4h 41mORD-PUJ
$182
5/1Wed
multi-stopSpirit Airlines
9h 30mSJU-ORD
5/7Tue
multi-stopSpirit Airlines
10h 35mORD-SJU
$188
4/30Tue
multi-stopAmerican Airlines
17h 00mSJU-ORD
5/4Sat
multi-stopAmerican Airlines
16h 57mORD-SJU
$245
4/30Tue
multi-stopAmerican Airlines
17h 00mSJU-ORD
5/4Sat
multi-stopAmerican Airlines
11h 31mORD-SJU
$275
4/28Sun
multi-stopUnited Airlines
7h 35mSJU-ORD
4/30Tue
multi-stopUnited Airlines
8h 48mORD-SJU
$311
5/1Wed
multi-stopUnited Airlines
10h 35mSJU-ORD
5/5Sun
multi-stopUnited Airlines
8h 48mORD-SJU
$356
5/1Wed
multi-stopDelta
17h 39mPUJ-ORD
5/5Sun
multi-stopDelta
15h 05mORD-PUJ
$461
4/28Sun
multi-stopJetBlue
15h 01mSDQ-ORD
5/4Sat
multi-stopJetBlue
13h 20mORD-SDQ
$925
4/29Mon
multi-stopJetBlue
15h 01mSDQ-ORD
5/22Wed
multi-stopJetBlue
10h 37mORD-SDQ
$949

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