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Cheap Flights from O'Hare Intl to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Montego Bay
Montego Bay1 stop$470
Kingston
Kingston1 stop$546
Montego Bay
Montego Bay1 stop$470
Kingston
Kingston1 stop$546
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to Jamaica flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Chicago O'Hare Intl Airport to Jamaica cheaper or more expensive than last year?

Fares from Chicago O'Hare Intl Airport to Jamaica are running about 6% lower than they were around this time last year, averaging $545 round-trip.

What are the cheapest fares from Chicago O'Hare Intl Airport to Jamaica right now?

Here are the cheapest round-trip fares from Chicago O'Hare Intl Airport to Jamaica on KAYAK in the last week:

• Montego Bay Sangster Intl (MBJ) from $470
• Kingston Norman Manley (KIN) from $546
• Ocho Rios Boscobel (OCJ) from $687

What’s the cheapest month to fly from Chicago O'Hare Intl Airport to Jamaica?

April is the cheapest time of year to fly, with average fares of $477. Prices are highest in December, when average flight costs increase to around $713.

When is the best time to book flights from Chicago O'Hare Intl Airport to Jamaica?

Book your flights 7 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 17% compared to booking last-minute (within 2 weeks of departure).

Which airport in Jamaica is the cheapest to fly to from Chicago O'Hare Intl Airport?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Jamaica are:

• Montego Bay Sangster Intl (MBJ) (avg. price $554)
• Kingston Norman Manley (KIN) (avg. price $665)
• Ocho Rios Boscobel (OCJ) (avg. price $823)

What’s the cheapest day to fly from Chicago O'Hare Intl Airport to Jamaica?

Monday tends to be the cheapest day to fly from Chicago O'Hare Intl Airport to Jamaica, while Thursday is the most expensive. Fares run about 14% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago O'Hare Intl Airport to Jamaica?

Data from the past 12 months shows it's cheapest to fly to Jamaica during the evening with average prices of $517. The night is the most expensive time to fly, with average prices of $614.

Key details for Chicago O'Hare Intl Airport to Jamaica flights

Low season

September

Cheapest flight

$184
Beat the crowds with an average 47% drop in travelers.
The most popular month to fly with an average 33% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Montego Bay

Your Chicago O'Hare Intl Airport to Jamaica flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago O'Hare Intl Airport to Jamaica?

    Fares from Chicago O'Hare Intl Airport to Jamaica are around their usual level right now. A round-trip under $456 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch price changes.

  • How much should I budget for a flight from Chicago O'Hare Intl Airport to Jamaica?

    Over the past 12 months, round-trip fares from Chicago O'Hare Intl Airport to Jamaica have ranged from $456 to $765.

  • What are the main airports serving Jamaica?

    Jamaica has 4 airports. The three busiest are Montego Bay Sangster Intl (MBJ) (89% of arrivals), Kingston Norman Manley (KIN) (10%) and Ocho Rios Boscobel (OCJ) (1%).

  • What airlines fly nonstop from Chicago O'Hare Intl Airport to Jamaica?

    Based on the flight schedule for the next 3 months, 2 airlines offer nonstop flights on this route:

    • United Airlines
    • American Airlines

  • Where in Jamaica can I fly nonstop from Chicago O'Hare Intl Airport?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Chicago O'Hare Intl Airport to Montego Bay.

  • Is it cheaper to fly with a layover from Chicago O'Hare Intl Airport to Jamaica?

    Yes, nonstop flights from Chicago O'Hare Intl Airport to Jamaica average $569 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Fort Lauderdale (FLL) (avg. price $471)
    • Toronto Pearson Intl (YYZ) (avg. price $498)
    • Montreal Pierre Elliott Trudeau Intl (YUL) (avg. price $507)

  • How long is a flight from Chicago O'Hare Intl Airport to Jamaica?

    Flights from Chicago O'Hare Intl Airport to Jamaica take 4h 11m on average.

  • Which cabin classes are available on flights from Chicago O'Hare Intl Airport to Jamaica?

    On flights from Chicago O'Hare Intl Airport to Jamaica you can book Economy Class, Premium Economy Class, Business Class or First Class.

  • What are some popular landmarks in Jamaica?

    KAYAK travelers' favorite landmarks in Jamaica include:

    • Doctor's Cave Bathing Club
    • Cornwall Beach
    • Fort Montego Craft Market
    • AquaSol Theme Park

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to Jamaica?

    The earliest nonstop flight from Chicago O'Hare Intl Airport to Jamaica departs at 8:40 am and the latest departs at 10:05 am. Nonstop flights take about 4h 11m.

Your guide to booking Chicago O'Hare Intl Airport to Jamaica flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 7 weeks before your trip. KAYAK data shows fares in this window are around 17% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for April when flights are typically cheapest and avoid December when prices are at their highest.
  • Flying on Monday is usually the cheapest. Flights on Thursday cost about 14% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Montego Bay Sangster Intl (MBJ) is the cheapest airport to fly into from Chicago O'Hare Intl Airport. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Montego Bay, which is the most popular destination in Jamaica. From there, it's easy to continue on to other popular destinations such as Negril, Ocho Rios and Kingston.
  • If you want the shortest trip, choose the Chicago O'Hare Intl Airport to Jamaica nonstop route. If you'd rather save money, the route via Fort Lauderdale (FLL) is usually the cheapest.

Reviews of the top 4 airlines serving from O'Hare Intl to Jamaica

 
Need help choosing which airline to fly with from O'Hare Intl to Jamaica? 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.
7.8
DeltaOverall score based on 8697 reviews
8.5Crew
7.8Comfort
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

4.0 OkayKathryn, Oct 2026
Read more Delta reviews

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

It was a smooth flight and the pilot was very pleasant

I'll nevere ever give up jet blue for years now and I will never change

JetBlue has too many delayed flights. I cant recall in the past two years flying with JetBlue without some form a delays. I expect better B6.

The communication was lacking. They delayed us over 8 hours keeping us on the plane, stopped for mechanical errors and then for the captain being over duty hours and then again for mechanical errors taking us to a different state and airport. It wasn’t fun, a lot of time and money lost. we felt trapped and hungry. A whole days of activities and vacation lost. I would have liked better communication and for them to allow us off the plane until everything was figured out. Also why couldn’t they share the food that was on the plane ? Snacks are not nutritious.

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.

More options for your flight from O'Hare Intl to Jamaica

Complete your trip to Jamaica with a hotel stay or car rental