$115 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 5/3. 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 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

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 8 - Mon, May 11
Frontier Logo
6:09 pm - 11:13 pm
SJU
-
ORD
30h 04m
1 stop
Frontier Logo
7:52 pm - 4:01 am
ORD
-
SJU
7h 09m
1 stop
$201Frontier
Wed, Jun 10 - Sun, Aug 30
American Airlines Logo
2:30 pm - 7:15 pm
MBJ
-
ORD
4h 45mnonstop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$281American Airlines
Wed, May 13 - Sun, May 17
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
9:45 am - 3:37 pm
ORD
-
MBJ
5h 52m
1 stop
$286American Airlines
Tue, May 12 - Sat, May 30
United Airlines Logo
2:40 pm - 12:45 am
MBJ
-
ORD
10h 05m
1 stop
United Airlines Logo
5:00 pm - 3:10 pm
ORD
-
MBJ
22h 10m
1 stop
$291United Airlines
Wed, May 13 - Mon, May 18
United Airlines Logo
2:40 pm - 1:27 am
MBJ
-
ORD
10h 47m
1 stop
United Airlines Logo
9:56 pm - 1:30 pm
ORD
-
MBJ
15h 34m
1 stop
$292United Airlines
Thu, Apr 2 - Tue, Apr 7
Air Canada Logo
9:10 pm - 5:50 pm
NAS
-
ORD
21h 40m
1 stop
Air Canada Logo
6:40 pm - 8:05 pm
ORD
-
NAS
24h 25m
1 stop
$373Air Canada
Mon, Apr 13 - Thu, Apr 16
Air Canada Logo
9:10 pm - 10:53 am
NAS
-
ORD
14h 43m
2 stops
Air Canada Logo
7:55 am - 8:05 pm
ORD
-
NAS
11h 10m
1 stop
$376Air Canada
Fri, Apr 10 - Mon, Apr 13
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
8:06 am - 1:40 am
ORD
-
POS
16h 34m
1 stop
$417Copa Airlines
Sat, Apr 25 - Sat, May 2
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
3:21 pm - 1:46 am
ORD
-
POS
9h 25m
1 stop
$455Copa Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$115
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from San Juan Airport 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.
7.5
Copa AirlinesOverall score based on 1568 reviews
6.8Entertainment
7.4Comfort
7.8Boarding
6.8Food
8.1Crew
Airline reviews

Do not book it’s a scam! They stole $1200 from me

2.0 MediocreTalicia, Mar 2026
PTY - RDU
Read more Copa Airlines reviews

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

A lot things happened in this trip.The fly should be less stress.

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

Some of the Air hostesses are not that friendly. Need improvement

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

Great experience with a crew always thinking in the passenger

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

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.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

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.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

Got denied my flight was told on Google that Air Canada was supposed to book me a flight back home because I never was able to go to my destination. They did not help me whatsoever. I had to book a whole new flight for that reason I would write this is zero

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

We left over 2 hours late and they didn't even give us a complimentary snack, when getting to the desk I asked if I could be put in a row with only 1 other person or an empt y one I was told the flight was full when the last two rows were empty. All around over it

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

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.

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
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Hammond
Des Plaines
Hoffman Estates
Willowbrook
Portage
South Holland
Delavan
Northbrook
Lansing
Pleasant Prairie
Lisle
Elmhurst
Valparaiso

Everything you need to know for your flight to O'Hare Intl

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