$111 Find Cheap Flights from Caribbean Islands 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 Islands 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 Islands 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 Islands to O'Hare Intl

Sat, Oct 11 - Fri, Oct 17
Spirit Airlines Logo
9:48 am - 1:56 pmSJU-ORD
5h 08mnonstop
Spirit Airlines Logo
7:51 pm - 2:12 pmORD-SJU
17h 21m1 stop
$181Spirit Airlines
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Thu, Oct 2 - Mon, Oct 6
Spirit Airlines Logo
11:59 am - 5:39 pmSJU-ORD
6h 40m1 stop
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
$186Spirit Airlines
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Fri, Oct 31 - Sun, Nov 2
Frontier Logo
5:51 pm - 11:30 amSJU-ORD
18h 39m2 stops
Frontier Logo
5:40 am - 4:54 pmORD-SJU
9h 14m1 stop
$207Frontier
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Thu, Oct 23 - Mon, Oct 27
United Airlines Logo
3:56 pm - 8:03 pmSJU-ORD
5h 07mnonstop
United Airlines Logo
2:20 pm - 8:00 pmORD-SJU
4h 40mnonstop
$218United Airlines
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Wed, Oct 22 - Mon, Oct 27
United Airlines Logo
1:05 am - 8:38 amSJU-ORD
8h 33m1 stop
United Airlines Logo
8:55 am - 2:40 pmORD-SJU
4h 45mnonstop
$223United Airlines
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Wed, Oct 22 - Mon, Oct 27
Frontier Logo
1:59 am - 11:39 pmSJU-ORD
22h 40m2 stops
Frontier Logo
6:40 am - 3:24 pmORD-SJU
7h 44m1 stop
$226Frontier
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Fri, Oct 24 - Mon, Oct 27
Delta Logo
5:43 pm - 11:58 pmSJU-ORD
7h 15m1 stop
Delta Logo
7:00 am - 4:25 pmORD-SJU
8h 25m1 stop
$227Delta
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Thu, Oct 30 - Sun, Nov 2
American Airlines Logo
2:35 pm - 11:58 pmSJU-ORD
10h 23m1 stop
American Airlines Logo
5:50 am - 10:52 pmORD-SJU
15h 02m1 stop
$233American Airlines
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Tue, Oct 7 - Sat, Oct 11
American Airlines Logo
1:50 pm - 6:23 pmMBJ-ORD
4h 33mnonstop
American Airlines Logo
9:45 pm - 2:15 pmORD-MBJ
16h 30m1 stop
$338American 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
5:40 am - 8:36 pmORD-MBJ
13h 56m1 stop
$377Delta
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Everything you should know

Cheapest round-trip
$181
Typical prices: $223-428
Spirit Airlines
Sat 10/11Fri 10/17
SJU - ORD • Non-stop
Cheapest non-stop
$187
Typical prices: $222-454
Spirit Airlines
Fri 10/24Mon 10/27
SJU - 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$111
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 Islands to Chicago O'Hare Airport flights

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands 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 Islands 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 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 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 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 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 Islands 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 Islands to O'Hare Intl

 
Need help choosing which airline to fly with from Caribbean Islands 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 7954 reviews
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

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.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

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.

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.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

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.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

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
Gurnee
South Haven
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Merrillville
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Hoffman Estates
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Pleasant Prairie
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Lansing

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