$108 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 11/15. 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

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Cheap Flights from Caribbean to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to O'Hare Intl 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 to O'Hare Intl

Fri, Oct 24 - Sat, Oct 25
Spirit Airlines Logo
7:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
Spirit Airlines Logo
3:00 pm - 8:40 pmORD-SJU
4h 40mnonstop
$178Spirit Airlines
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Sat, Oct 18 - Fri, Oct 24
Spirit Airlines Logo
9:48 am - 1:56 pmSJU-ORD
5h 08mnonstop
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
$192Spirit Airlines
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Sun, Oct 26 - Wed, Oct 29
Frontier Logo
9:19 pm - 7:10 amSJU-ORD
10h 51m1 stop
Frontier Logo
6:40 am - 5:54 pmORD-SJU
10h 14m1 stop
$197Frontier
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Fri, Oct 3 - Wed, Oct 8
Frontier Logo
7:15 am - 3:50 pmSJU-ORD
9h 35m1 stop
Frontier Logo
6:40 am - 3:24 pmORD-SJU
7h 44m1 stop
$204Frontier
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Fri, Oct 24 - Sun, Oct 26
United Airlines Logo
3:56 pm - 8:03 pmSJU-ORD
5h 07mnonstop
United Airlines Logo
8:55 am - 2:40 pmORD-SJU
4h 45mnonstop
$218United Airlines
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Thu, Oct 23 - Thu, Oct 30
United Airlines Logo
4:55 pm - 11:15 pmSJU-ORD
7h 20m1 stop
United Airlines Logo
2:20 pm - 8:00 pmORD-SJU
4h 40mnonstop
$223United Airlines
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Fri, Oct 24 - Mon, Oct 27
Delta Logo
2:22 pm - 8:23 pmSJU-ORD
7h 01m1 stop
Delta Logo
7:00 am - 4:25 pmORD-SJU
8h 25m1 stop
$227Delta
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Sat, Oct 25 - Fri, Oct 31
American Airlines Logo
5:25 am - 2:11 pmSJU-ORD
9h 46m1 stop
American Airlines Logo
7:05 pm - 12:39 pmORD-SJU
16h 34m1 stop
$232American Airlines
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Fri, Nov 14 - Fri, Dec 5
American Airlines Logo
2:04 pm - 5:40 pmMBJ-ORD
4h 36mnonstop
American Airlines Logo
10:15 am - 3:22 pmORD-MBJ
4h 07mnonstop
$340American Airlines
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Fri, Dec 12 - Fri, Jan 2
Delta Logo
5:59 pm - 12:01 amMBJ-ORD
7h 02m1 stop
Delta Logo
7:00 am - 8:36 pmORD-MBJ
12h 36m2 stops
$377Delta
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Everything you should know

Cheapest round-trip
$178
Overall average: $339
Spirit Airlines
Fri 10/24Sat 10/25
SJU - ORD • Non-stop
Cheapest one-way
$108
Typical prices: $192-372
Arajet
Sat 11/15
PUJ - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to O'Hare Intl!
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$108
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 3% lower on average.
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.

Reviews of the 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.
7.9
DeltaOverall score based on 7964 reviews
8.2Boarding
8.5Crew
7.3Food
7.9Comfort
7.9Entertainment
Airline reviews

Awful. Flight from Cape Town was cancelled, rebooked for another day through Johannesburg, was downgraded to economy

4.0 OkayOlaf, Sep 2025JNB - ATL
Read more Delta reviews

Awful. Flight from Cape Town was cancelled, rebooked for another day through Johannesburg, was downgraded to economy

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

The airport crew helped a lot, what I didn’t like? We were not informed that we needed to pick our luggage’s, if the crew at the luggage center didn’t tell me I would have been home without my belongings, I was heading out to my next connecting flight while looking for what gate to go to, I asked one of the crews for help, he told me and he also told me to not forget to grab my luggage’s which was chocking, because on my way out the country that wasn’t required, I just hope none of your customers lost their luggage’s because of this.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

The flight crew was friendly. I tried to adjust my seat online ahead of time but no option existed without additional fees. My friend asked at the gate about a seat change and was able to make it happen. That was great! The flight crew moved a very tall gentleman and his companion which allowed us to have more space which was nice. Overall, good experience. Appreciated the blanket and pillow.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Didn’t like that we weren’t even offered a water. And really didn’t like the male flight attendant, he had major attitude. The flight however was good, pilots got us there in time safely.

The seats are too small the plane makes weird noise when landing 🛬

I never made my flight because of their poor service, as I said in my other review: I never made this flight. When I got to the airport I had a message to say that the flight was delayed and would be getting into Fort Lauderdale at 10 pm. My connecting flight was due to leave around 10:10 pm so there is no way I would have made the connection. I went back to the Spirit desk and tried to explain this to a desk agent who didn't understand. Eventually her supervisor came over and explained it. The desk agent was unhelpful and only offered options that would have required getting a hotel overnight. She offered no hotel or meal vouchers and when I said that it seemed my only option was to go to another airline she told me I needed to make a decision because they were closing the desk and would not be back till 3 pm. I went to Delta and had to pay extra but they could help get me back to Orlando. I now have to file a claim against Spirit and I am just glad I paid for insurance. Very unhappy and very poor service.

I never made this flight. When I got to the airport I had a message to say that the flight was delayed and would be getting into Fort Lauderdale at 10 pm. My connecting flight was due to leave around 10:10 pm so there is no way I would have made the connection. I went back to the Spirit desk and tried to explain this to a desk agent who didn't understand. Eventually her supervisor came over and explained it. The desk agent was unhelpful and only offered options that would have required getting a hotel overnight. She offered no hotel or meal vouchers and when I said that it seemed my only option was to go to another airline she told me I needed to make a decision because they were closing the desk and would not be back till 3 pm. I went to Delta and had to pay extra but they could help get me back to Orlando. I now have to file a claim against Spirit and I am just glad I paid for insurance. Very unhappy and very poor service.

I missed my connecting flight from MBJ to IAH via FLL. The plane was late to arrive to MBJ and the crew has a very slow turnover. (Low energy, lacksdasical team and then waiting for baggage to be loaded long after all passengers were seated.Claiming baggage in FLL took over 35 minutes. It was a train wreck.

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
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