$112 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 4/29. 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 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, May 8 - Sun, May 10
Frontier Logo
3:18 pm - 10:39 pm
SJU
-
ORD
8h 21m
1 stop
Frontier Logo
10:25 am - 2:01 am
ORD
-
SJU
14h 36m
1 stop
$183Frontier
Thu, May 21 - Mon, May 25
Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:59 am - 6:56 am
ORD
-
SJU
4h 57mnonstop
$191Frontier
Wed, Apr 29 - Mon, May 4
Spirit Airlines Logo
3:21 am - 1:05 pm
SJU
-
ORD
10h 44m
1 stop
Spirit Airlines Logo
7:50 am - 2:06 am
ORD
-
SJU
17h 16m
1 stop
$193Spirit Airlines
Fri, May 1 - Mon, May 4
Spirit Airlines Logo
12:57 pm - 12:24 am
SJU
-
ORD
12h 27m
1 stop
Spirit Airlines Logo
7:50 am - 2:06 am
ORD
-
SJU
17h 16m
1 stop
$200Spirit Airlines
Fri, May 29 - Mon, Aug 31
American Airlines Logo
2:30 pm - 7:16 pm
MBJ
-
ORD
4h 46mnonstop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$261American Airlines
Fri, May 29 - Mon, Aug 31
American Airlines Logo
2:30 pm - 7:16 pm
MBJ
-
ORD
4h 46mnonstop
American Airlines Logo
8:34 pm - 9:25 am
ORD
-
MBJ
12h 51m
1 stop
$266American Airlines
Fri, May 22 - Sat, Jun 13
United Airlines Logo
4:12 pm - 11:26 pm
MBJ
-
ORD
7h 14m
1 stop
United Airlines Logo
9:21 pm - 3:26 pm
ORD
-
MBJ
18h 05m
1 stop
$271United Airlines
Thu, Apr 23 - Thu, Apr 30
United Airlines Logo
4:12 pm - 11:43 pm
MBJ
-
ORD
7h 31m
1 stop
United Airlines Logo
4:25 pm - 3:10 pm
ORD
-
MBJ
22h 45m
1 stop
$291United Airlines
Sat, Aug 1 - Mon, Aug 31
Air Canada Logo
12:30 pm - 9:00 am
MBJ
-
ORD
20h 30m
1 stop
Air Canada Logo
8:40 pm - 11:20 am
ORD
-
MBJ
14h 40m
1 stop
$337Air Canada
Sun, Apr 19 - Mon, Apr 27
Air Canada Logo
1:20 am - 3:15 pm
POS
-
ORD
14h 55m
1 stop
Air Canada Logo
4:15 pm - 12:20 am
ORD
-
POS
31h 05m
1 stop
$340Air Canada
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$112
Best time to beat the crowds but there is an average 8% 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.

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.
7.4
United AirlinesOverall score based on 9409 reviews
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
7.3Comfort
Airline reviews

They never clean the toilet, and the food is worse

4.0 OkayAnonymous, Mar 2026
HND - ORD
Read more United Airlines reviews

They never clean the toilet, and the food is worse

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.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

It was a pretty smooth flight, I tend to get mini anxiety attacks during flights, however, this time was pretty smooth and I was able to relax. The only thing, I was having issues to connect to the Flyfi internet. I was not able to connect at all, I turned off my phone a couple times and didnt work.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Very smooth flight, good legroom with the "even more room" seats. Entertainment choice was excellent, wifi on board, plane was modern. Pilot got a round of applause for a smooth landing in very blustery conditions. Love flying with them. Check in was OK too. We were too early so we had to wait until groundstaff showed up 3hrs before the flight.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

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.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Had to pay for my bag a mini weekender bag 100 dollar fee

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

Frontier line changes my flight schedule with out my authorization. They never ask me and with out my concern they cut off 4 hours of my vacation they force my to leave 4 hours early from Puerto Rico.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

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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Des Plaines
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