$148 Find Cheap Flights from Chicago to Jamaica

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 6/1. 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 72 hours
Montego Bay
Montego Baynonstop$338
Kingston
Kingston1 stop$516
Montego Bay
Montego Baynonstop$338
Kingston
Kingston1 stop$516

Book Cheap Chicago to Jamaica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Jamaica 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 Chicago to Jamaica

Tue, Jul 7 - Sat, Jul 11
American Airlines Logo
9:20 am - 1:36 pm
ORD
-
MBJ
4h 16mnonstop
American Airlines Logo
2:36 pm - 7:27 pm
MBJ
-
ORD
4h 51mnonstop
$338American Airlines
Sun, Aug 16 - Thu, Aug 20
American Airlines Logo
5:00 am - 1:58 pm
ORD
-
MBJ
8h 58m
1 stop
American Airlines Logo
2:20 pm - 7:05 pm
MBJ
-
ORD
4h 45mnonstop
$342American Airlines
Tue, Oct 27 - Sun, Nov 1
American Airlines Logo
5:22 am - 1:05 pm
ORD
-
MBJ
7h 43m
1 stop
American Airlines Logo
2:19 pm - 6:00 pm
MBJ
-
ORD
4h 41mnonstop
$347American Airlines
Mon, May 18 - Thu, May 21
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
2:55 pm - 7:10 am
MBJ
-
ORD
16h 15m
1 stop
$348American Airlines
Mon, Oct 5 - Tue, Oct 27
United Airlines Logo
9:30 pm - 11:43 am
ORD
-
MBJ
14h 13m
1 stop
United Airlines Logo
1:48 pm - 6:16 pm
MBJ
-
ORD
4h 28mnonstop
$362United Airlines
Tue, Jul 21 - Fri, Jul 24
Frontier Logo
6:00 am - 12:27 pm
MDW
-
MBJ
6h 27m
1 stop
Frontier Logo
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
$392Frontier
Sat, Jul 18 - Fri, Jul 24
Frontier Logo
6:00 am - 12:27 pm
MDW
-
MBJ
6h 27m
1 stop
Frontier Logo
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
$406Frontier
Tue, Jul 21 - Tue, Jul 28
Copa Airlines Logo
1:20 am - 1:54 pm
ORD
-
KIN
12h 34m
1 stop
Copa Airlines Logo
2:56 pm - 4:00 am
KIN
-
ORD
13h 04m
1 stop
$516Copa Airlines
Tue, May 26 - Tue, Jun 2
Delta Logo
6:23 am - 8:00 pm
MDW
-
KIN
13h 37m
1 stop
Delta Logo
9:00 am - 9:09 pm
KIN
-
MDW
12h 09m
1 stop
$576Delta
Sat, May 30 - Tue, Jun 2
Delta Logo
8:10 am - 8:00 pm
ORD
-
KIN
11h 50m
1 stop
Delta Logo
9:00 am - 4:56 pm
KIN
-
ORD
7h 56m
1 stop
$576Delta
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 72 hours was to Montego Bay, at $317 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 72 hours was $317.

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 $551 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 $551.

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 $518, 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 December, when tickets cost $84 (return) on average. On the other hand, the most expensive months are May and February, when the average cost of round-trip tickets is $277 and $268 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 7 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$148
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 9% 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 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.
7.9
SouthwestOverall score based on 4305 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

2.0 MediocreJoshua, May 2026
TPA - LAS
Read more Southwest reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

The airline cancel mi flight, lost a lot of money!!!

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

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.