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Find cheap flights from Chicago to Jamaica from $99

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Jamaica departing on 5/14. 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
0 bags
Fri 5/24
Fri 5/31

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Best Jamaica Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay1 stop$231
Kingston
Kingston1 stop$326

Good to know

Low season

September

High season

March

Cheapest flight

$99
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago O'Hare Airport to Montego Bay

FAQs - booking Jamaica flights

  • Are there airlines that offer direct flights to Jamaica from Chicago?

    If you’d like to travel to Jamaica from Chicago on a direct flight, you can travel with United Airlines or American Airlines, as these two airlines offer direct flights from Chicago’s O’Hare International Airport to Sangster International Airport.

  • Which Jamaican airport is closest to Montego Bay?

    Suppose your final destination in Jamaica is Montego Bay. In that case, you should book a flight from Chicago that lands at Sangster International Airport, given that this airport is the closest airport to the city.

  • How will I get to Montego Bay from Sangster International Airport?

    To get to Montego Bay from Sangster International Airport, you can board a taxi, van, or bus. Onboard any, you won’t spend a fortune, as these transport vehicles offer their services at pocket-friendly rates.

  • Which of the airlines that fly from Chicago to Jamaica are eco-friendly?

    If you’re an eco-conscious traveler, you should travel with American Airlines as this air travel company has taken eco-friendly steps, such as funding sustainable aviation fuel research, partnering with carbon offset companies, and investing in planes that consume less fuel and emit fewer gases.

  • How does KAYAK find such low prices on flights from Chicago to Jamaica?

    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 Chicago to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jamaica from Chicago 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 Chicago to Jamaica?

    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 Jamaica with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Jamaica?

    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 Jamaica from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Jamaica

  • Morning departure is around 15% more expensive than an evening flight, on average*.
  • Most flights from Chicago to Jamaica usually take off from Chicago’s O’Hare International Airport. However, few depart Chicago to Jamaica at Chicago Midway International Airport. Given that the flights to Jamaica from Midway International Airport are limited, you should choose O’Hare International Airport. One of the busiest transportation networks in the country, this airport has amenities like clean and accessible washrooms, large waiting lounges, payphones, and ATMs. While waiting for your flight at this airport, you’ll be able to have a meal, shop, and even appreciate art.
  • When booking a flight from Chicago to Jamaica, you should choose one that lands at an airport near the region you plan to visit. If you are traveling to Jamaica’s western region, you should book a flight that lands at Sangster International Airport. However, if you plan on visiting Jamaica’s eastern region, you should book a flight that lands at Norman Manley International Airport.
  • If you plan on renting a car that you’ll travel in with your kid while in Jamaica, it’s advisable that you carry an approved child safety seat. This is because, in Jamaica, young children are required to be seated in approved child safety seats while being transported in a car. If you don’t own one, you should see if the car rental company can provide you with one.
  • To be allowed through airport security once you land in Jamaica, you’ll need a passport with adequate blank pages and proof that you’ve got enough money to comfortably stay in the country. Kindly note that if you plan on staying in the country for more than 90 days, you’ll also have to avail your passport.
  • Jamaican airport authorities have a reputation for being extremely strict. Thus, to get cleared by them, kindly ensure that you’ve got your documents in check.
  • Norman Manley International Airport in Kingston is the airport with the most flights to other Caribbean countries. If you plan on flying to other Caribbean countries once you’ve toured Jamaican, this is the airport you should be close to.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Chicago to Jamaica

 
Need help choosing which airline to fly with from Chicago 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.
8.0
DeltaOverall score based on 11004 reviews
7.9comfort
8.2boarding
8.0entertainment
8.6crew
7.5food
Airline reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

All good, useful to have the united app from check in to boarding

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

what I like about Spirit is that the pilot and crew are good communicators. The plane itself - well, its a budget airline and you get what is expected, But I generally just feel safer, somehow, when I know more about what is going on - and Spirit has always done a good job of telling me what is going on: why the delay, why the turbulence, why this and that... and that means a lot to me.

The crew was courteous and are very well prepared for the job.

I paid just under 200 for flight and luggage, then paid 200 to change the flight, then paid 100 for a carry on. Then the cancelled the flight. Of the 500 I spent they refunded 250. I bought a delta flight for 270 never flew with spirit, but spirit kept 250, not even refunding the 100 for the carry on though they cancelled the flight (for weather on a day with only a slight rain ).

Flight attendants heavily pushed their affinity credit card. Very annoying

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Chicago to Jamaica

Recent round-trip flight deals

5/11Sat
1 stopFrontier
9h 19mORD-MBJ
5/15Wed
1 stopFrontier
8h 55mMBJ-ORD
$231
5/11Sat
1 stopFrontier
9h 19mORD-MBJ
5/15Wed
1 stopFrontier
8h 55mMBJ-ORD
$235
5/5Sun
1 stopFrontier
7h 59mORD-MBJ
5/8Wed
1 stopFrontier
8h 55mMBJ-ORD
$243
6/1Sat
1 stopSpirit Airlines
6h 41mORD-MBJ
6/5Wed
1 stopSpirit Airlines
10h 08mMBJ-ORD
$288
6/1Sat
1 stopSpirit Airlines
6h 41mORD-MBJ
6/4Tue
1 stopSpirit Airlines
10h 44mMBJ-ORD
$300
7/7Sun
nonstopAmerican Airlines
3h 55mORD-MBJ
7/11Thu
nonstopAmerican Airlines
4h 30mMBJ-ORD
$393
5/11Sat
1 stopAmerican Airlines
7h 25mORD-MBJ
5/15Wed
nonstopAmerican Airlines
4h 30mMBJ-ORD
$396
5/5Sun
1 stopDelta
7h 10mMDW-MBJ
5/8Wed
1 stopDelta
8h 56mMBJ-MDW
$468
9/8Sun
2 stopsDelta
17h 27mORD-MBJ
9/13Fri
2 stopsDelta
16h 57mMBJ-ORD
$472
8/3Sat
2 stopsAir Canada
40h 51mORD-KIN
8/13Tue
2 stopsAir Canada
30h 25mKIN-ORD
$692

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Recent one-way flight deals

5/14Tue
1 stopFrontier
8h 53mORD-MBJ
$99
5/14Tue
1 stopFrontier
11h 04mMDW-MBJ
$99
5/7Tue
2 stopsSpirit Airlines
13h 41mORD-MBJ
$131
6/6Thu
1 stopSpirit Airlines
16h 38mORD-KIN
$137
5/14Tue
nonstopAmerican Airlines
4h 00mORD-MBJ
$177
6/6Thu
2 stopsDelta
10h 24mMDW-KIN
$202
6/6Thu
2 stopsDelta
11h 11mORD-KIN
$202
4/28Sun
2 stopsAmerican Airlines
20h 10mORD-MBJ
$225
5/19Sun
1 stopUnited Airlines
15h 48mORD-MBJ
$441
5/22Wed
1 stopUnited Airlines
8h 36mORD-MBJ
$681

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Last minute flights from Chicago to Jamaica

Last minute flight, train and bus deals

4/28Sun
multi-stopFrontier
7h 59mORD-MBJ
4/30Tue
multi-stopFrontier
25h 21mMBJ-ORD
$334
4/27Sat
multi-stopFrontier
9h 19mORD-MBJ
5/3Fri
multi-stopFrontier
8h 55mMBJ-ORD
$340
4/26Fri
multi-stopFrontier
16h 30mMDW-MBJ
4/28Sun
multi-stopFrontier
12h 06mMBJ-MDW
$360
4/26Fri
multi-stopAmerican Airlines
7h 37mORD-MBJ
5/3Fri
nonstopAmerican Airlines
4h 35mMBJ-ORD
$396
4/26Fri
multi-stopAmerican Airlines
7h 37mORD-MBJ
5/3Fri
multi-stopAmerican Airlines
9h 17mMBJ-ORD
$405
4/27Sat
multi-stopSpirit Airlines
9h 17mORD-MBJ
5/1Wed
multi-stopSpirit Airlines
11h 24mMBJ-ORD
$441
4/27Sat
multi-stopDelta
7h 10mMDW-MBJ
5/1Wed
multi-stopDelta
16h 12mMBJ-MDW
$468
4/27Sat
multi-stopSpirit Airlines
18h 15mORD-MBJ
5/1Wed
multi-stopSpirit Airlines
11h 24mMBJ-ORD
$469
4/26Fri
multi-stopDelta
17h 40mORD-MBJ
5/3Fri
multi-stopDelta
18h 15mMBJ-ORD
$472
4/26Fri
nonstopUnited Airlines
4h 00mORD-MBJ
4/30Tue
nonstopUnited Airlines
4h 24mMBJ-ORD
$2,958

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Flights to Jamaica

Return flight deals:

Jamaica - Chicago

Cabin classes:

$1,255
$435
$1,396
$387