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Find cheap flights from Chicago to Jamaica from $100

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 9/17. 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
Sat 6/15
Sat 6/22

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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$270
Kingston
Kingston2 stops$385

Good to know

Low season

September

High season

March

Cheapest flight

$100
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 14% 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 5% 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 10673 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

2.0 MediocreDevan, May 2024AUS - BOS
Read more about Delta reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The plane was FREEZING SEATS UNCOMFORTABLE Otherwise smooth Thank you

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

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.

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.

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Arrived 3 hours early and never made it past baggage drop

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Book cheap flights from Chicago to Jamaica

Recent round-trip flight deals

9/25Wed
1 stopSpirit Airlines
6h 41mORD-MBJ
10/2Wed
1 stopSpirit Airlines
11h 15mMBJ-ORD
$270
9/17Tue
1 stop
6h 41mORD-MBJ
9/20Fri
1 stop
25h 01mMBJ-ORD
$283
9/17Tue
1 stopFrontier
9h 13mMDW-MBJ
9/20Fri
1 stopFrontier
12h 42mMBJ-MDW
$288
9/1Sun
1 stopFrontier
9h 13mMDW-MBJ
9/7Sat
1 stopFrontier
12h 42mMBJ-MDW
$318
7/7Sun
nonstopAmerican Airlines
4h 00mORD-MBJ
7/11Thu
nonstopAmerican Airlines
4h 30mMBJ-ORD
$393
8/9Fri
1 stopAmerican Airlines
8h 30mORD-MBJ
8/16Fri
nonstopAmerican Airlines
4h 35mMBJ-ORD
$396
7/7Sun
2 stopsDelta
16h 20mORD-MBJ
7/11Thu
2 stopsDelta
18h 30mMBJ-ORD
$472
6/11Tue
1 stopDelta
14h 10mMDW-KIN
6/16Sun
1 stopDelta
12h 36mKIN-MDW
$474
7/13Sat
nonstopUnited Airlines
4h 00mORD-MBJ
7/21Sun
nonstopUnited Airlines
4h 24mMBJ-ORD
$503
7/14Sun
1 stopUnited Airlines
9h 26mORD-MBJ
7/21Sun
nonstopUnited Airlines
4h 24mMBJ-ORD
$508

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Recent one-way flight deals

9/17Tue
1 stopSpirit Airlines
6h 41mORD-MBJ
$100
8/27Tue
1 stopSpirit Airlines
6h 41mORD-MBJ
$101
8/13Tue
1 stopFrontier
9h 13mMDW-MBJ
$115
9/9Mon
1 stopSpirit Airlines
6h 41mORD-MBJ
$115
8/6Tue
1 stopFrontier
26h 57mORD-MBJ
$123
5/26Sun
nonstopAmerican Airlines
4h 00mORD-MBJ
$177
8/8Thu
1 stopAmerican Airlines
10h 28mORD-MBJ
$180
6/10Mon
1 stopDelta
14h 10mMDW-KIN
$202
8/26Mon
2 stopsDelta
17h 23mMDW-MBJ
$211
6/6Thu
1 stopUnited Airlines
17h 21mORD-MBJ
$246

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Last minute flights from Chicago to Jamaica

Last minute flight, train and bus deals

5/21Tue
multi-stop
6h 28mORD-MBJ
5/30Thu
multi-stop
10h 44mMBJ-ORD
$341
5/21Tue
multi-stop
6h 28mORD-MBJ
5/30Thu
multi-stop
34h 25mMBJ-ORD
$382
5/20Mon
nonstopAmerican Airlines
4h 00mORD-MBJ
5/24Fri
nonstopAmerican Airlines
4h 30mMBJ-ORD
$393
5/20Mon
multi-stopAmerican Airlines
14h 50mORD-MBJ
5/24Fri
nonstopAmerican Airlines
4h 30mMBJ-ORD
$398
5/21Tue
multi-stopSpirit Airlines
6h 41mORD-MBJ
5/30Thu
multi-stopSpirit Airlines
27h 38mMBJ-ORD
$483
5/19Sun
multi-stopFrontier
25h 55mORD-MBJ
5/21Tue
multi-stopFrontier
25h 59mMBJ-ORD
$487
5/21Tue
multi-stopSpirit Airlines
26h 25mORD-MBJ
5/30Thu
multi-stopSpirit Airlines
27h 38mMBJ-ORD
$525
5/19Sun
multi-stopFrontier
20h 41mMDW-MBJ
5/21Tue
multi-stopFrontier
24h 03mMBJ-MDW
$885
5/18Sat
multi-stopDelta
13h 56mMDW-KIN
5/21Tue
multi-stopDelta
32h 06mKIN-MDW
$971
5/21Tue
multi-stopDelta
9h 34mMDW-MBJ
5/26Sun
multi-stopDelta
14h 56mMBJ-MDW
$973

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Flights to Jamaica

Return flight deals:

Jamaica - Chicago

Cabin classes:

$1,255
$883
$1,110
$385