$147 Find Cheap Flights from Chicago to Jamaica - Compare and Save

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 11/9. 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.
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Cheap Flights from Chicago to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Montego Bay
Montego Bay2 stops$424
Kingston
Kingston2 stops$461
Montego Bay
Montego Bay2 stops$424
Kingston
Kingston2 stops$461
Booking Insights

KAYAK's insights & trends for Chicago to Jamaica flights

Get data-powered insights and trends into flights from Chicago to Jamaica to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Jamaica flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Jamaica from Chicago found in the last 5 days was to Montego Bay, at $397 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $397.

What is the cheapest time of day to fly to Jamaica?

The average price for all round-trip flights from Chicago to Jamaica depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Jamaica is generally in the morning, when round-trip flights cost $543 on average. The most expensive time of day to fly to Jamaica is generally in the morning, which is peak travel time and where the average cost of a ticket is $543.

Can I save money by flying with a layover from Chicago to Jamaica?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $523, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Jamaica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Jamaica is April, when tickets cost $480 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $677 and $617 respectively.

What’s the cheapest day of the week to fly from Chicago to Jamaica?

The average price of all round-trip flights from Chicago to Jamaica clicked on KAYAK for each day over the last 12 months.

For Chicago to Jamaica, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Jamaica back to Chicago, the best deals are generally found on Wednesday, with Monday being the most expensive.

How far in advance should I book a flight from Chicago to Jamaica?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Jamaica, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Jamaica, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low season

January

Cheapest flight

$147
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 5% lower on average.
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 from Chicago to Jamaica 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 from Chicago to Jamaica with an airline and back 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 from Chicago to Jamaica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Jamaica

  • 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.

Reviews of the 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
SouthwestOverall score based on 4218 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

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!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

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

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

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

Couldn't make the flight because connecting flight was canceled.

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

Everything you need to know for your flight from Chicago to Jamaica

Cabin class types available on flights to Jamaica

Cabin classes available on flights to Jamaica. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.