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$75 Find cheap flights from Caribbean to Chicago O'Hare 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 6/11. 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
Fri 7/5
Fri 7/12

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Good to know

Low season

January

High season

November

Cheapest flight

$75
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from San Juan Airport 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, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 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 10368 reviews
8.6Crew
7.4Food
7.9Comfort
8.2Boarding
8.0Entertainment
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Ongoing flight was delayed. Staff at bag recheck was able to get us on an earlier flight. With only 20 minutes till take off we feared our bags would not make the new earlier flight. We were most delighted that they did and were there when we landed. Delta came through

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

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

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

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

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

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.

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Book cheap flights from Caribbean to Chicago

Recent round-trip flight deals

7/2Tue
1 stopSpirit Airlines
9h 29mSJU-ORD
7/9Tue
1 stopSpirit Airlines
14h 41mORD-SJU
$136
8/14Wed
nonstopSpirit Airlines
4h 59mSJU-ORD
8/26Mon
1 stopSpirit Airlines
17h 30mORD-SJU
$139
7/4Thu
nonstopFrontier
5h 17mPUJ-ORD
7/16Tue
1 stopFrontier
21h 57mORD-PUJ
$248
7/10Wed
1 stopFrontier
9h 03mPUJ-ORD
7/16Tue
1 stopFrontier
28h 12mORD-PUJ
$249
10/23Wed
1 stopUnited Airlines
16h 01mPUJ-ORD
10/27Sun
nonstopUnited Airlines
4h 28mORD-PUJ
$311
7/4Thu
nonstopAmerican Airlines
4h 30mMBJ-ORD
7/9Tue
nonstopAmerican Airlines
4h 00mORD-MBJ
$357
8/25Sun
nonstopAmerican Airlines
4h 35mMBJ-ORD
9/2Mon
1 stopAmerican Airlines
6h 17mORD-MBJ
$362
8/23Fri
1 stopDelta
8h 22mGCM-ORD
8/25Sun
1 stopDelta
5h 30mORD-GCM
$409
8/1Thu
2 stopsDelta
17h 10mNAS-ORD
8/5Mon
1 stopDelta
16h 38mORD-NAS
$414
8/1Thu
1 stopUnited Airlines
15h 53mNAS-ORD
8/3Sat
nonstopUnited Airlines
3h 23mORD-NAS
$444

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Recent one-way flight deals

6/11Tue
1 stopSpirit Airlines
29h 59mSJU-ORD
$75
8/21Wed
1 stopSpirit Airlines
15h 01mSJU-ORD
$78
7/4Thu
nonstopFrontier
5h 17mPUJ-ORD
$101
7/31Wed
nonstopFrontier
5h 06mPUJ-ORD
$123
8/21Wed
2 stopsAmerican Airlines
9h 56mSJU-ORD
$143
8/3Sat
2 stopsAmerican Airlines
17h 50mSJU-ORD
$144
10/30Wed
1 stopUnited Airlines
12h 12mPUJ-ORD
$170
8/17Sat
1 stopDelta
6h 54mSJU-ORD
$172
6/11Tue
nonstopUnited Airlines
4h 59mPUJ-ORD
$183
9/21Sat
2 stopsDelta
19h 12mSDQ-ORD
$228

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Last minute flights from Caribbean to O'Hare Intl

Last minute flight, train and bus deals

6/7Fri
multi-stop
14h 31mSJU-ORD
6/18Tue
multi-stop
15h 12mORD-SJU
$238
6/7Fri
nonstopSpirit Airlines
5h 09mSJU-ORD
6/11Tue
multi-stopSpirit Airlines
21h 15mORD-SJU
$242
6/6Thu
multi-stopFrontier
9h 03mSJU-ORD
6/9Sun
multi-stopFrontier
9h 19mORD-SJU
$258
6/6Thu
multi-stopFrontier
23h 09mSJU-ORD
6/14Fri
multi-stopFrontier
7h 01mORD-SJU
$299
6/6Thu
multi-stopUnited Airlines
8h 58mMBJ-ORD
6/13Thu
multi-stopUnited Airlines
17h 21mORD-MBJ
$437
6/6Thu
nonstopAmerican Airlines
4h 30mMBJ-ORD
6/13Thu
multi-stopAmerican Airlines
15h 59mORD-MBJ
$468
6/7Fri
multi-stopAmerican Airlines
10h 50mSJU-ORD
6/11Tue
multi-stopAmerican Airlines
11h 45mORD-SJU
$470
6/6Thu
multi-stopUnited Airlines
9h 30mSJU-ORD
6/11Tue
multi-stopUnited Airlines
8h 32mORD-SJU
$475
6/6Thu
multi-stopDelta
23h 05mSDQ-ORD
6/14Fri
multi-stopDelta
29h 55mORD-SDQ
$558
6/9Sun
multi-stopDelta
12h 16mSJU-ORD
6/13Thu
multi-stopDelta
13h 35mORD-SJU
$3,242

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