$123 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 8/5. 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
1 adult, Economy

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Best Jamaica Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$300
Kingston
Kingston1 stop$367
Montego Bay
Montego Bay1 stop$300
Kingston
Kingston1 stop$367

Cheap Flights from Chicago to Jamaica

 
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

Sat, Jul 19 - Wed, Jul 23
Spirit Airlines Logo
5:38 pm - 9:53 amORD-MBJ
16h 15m1 stop
Spirit Airlines Logo
12:10 pm - 11:13 pmMBJ-ORD
11h 03m1 stop
$300Spirit Airlines
Find Deal
Sun, Aug 17 - Thu, Aug 21
Spirit Airlines Logo
6:50 pm - 11:09 amORD-MBJ
16h 19m1 stop
Spirit Airlines Logo
10:19 am - 5:45 pmMBJ-ORD
7h 26m1 stop
$311Spirit Airlines
Find Deal
Mon, Aug 25 - Fri, Aug 29
American Airlines Logo
8:30 am - 12:31 pmORD-MBJ
4h 01mnonstop
American Airlines Logo
2:00 pm - 6:30 pmMBJ-ORD
4h 30mnonstop
$370American Airlines
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Mon, Oct 13 - Tue, Oct 21
American Airlines Logo
8:05 am - 12:10 pmORD-MBJ
4h 05mnonstop
American Airlines Logo
2:20 pm - 6:50 pmMBJ-ORD
4h 30mnonstop
$371American Airlines
Find Deal
Mon, Aug 25 - Fri, Aug 29
Delta Logo
6:00 am - 11:55 amMDW-MBJ
5h 55m1 stop
Delta Logo
2:30 pm - 9:49 pmMBJ-MDW
7h 19m1 stop
$385Delta
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Sat, Aug 2 - Wed, Aug 6
Delta Logo
7:00 am - 3:34 pmORD-MBJ
8h 34m1 stop
Delta Logo
2:29 pm - 9:30 pmMBJ-ORD
7h 01m1 stop
$410Delta
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Sat, Jul 12 - Sat, Jul 19
United Airlines Logo
8:42 am - 12:49 pmORD-MBJ
4h 07mnonstop
United Airlines Logo
1:51 pm - 6:20 pmMBJ-ORD
4h 29mnonstop
$420United Airlines
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Tue, Jul 8 - Thu, Jul 10
Southwest Logo
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
Southwest Logo
2:55 pm - 11:40 pmMBJ-MDW
8h 45m1 stop
$420Southwest
Find Deal
Tue, Jul 8 - Thu, Jul 10
Southwest Logo
9:00 am - 1:00 pmMDW-MBJ
4h 00mnonstop
Southwest Logo
2:20 pm - 6:30 pmMBJ-MDW
4h 10mnonstop
$423Southwest
Find Deal
Sat, Jul 12 - Sat, Jul 19
United Airlines Logo
6:00 am - 1:10 pmORD-MBJ
7h 10m1 stop
United Airlines Logo
1:51 pm - 6:20 pmMBJ-ORD
4h 29mnonstop
$425United Airlines
Find Deal
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Jamaica.

The cheapest ticket to Jamaica from Chicago found in the last 72 hours was to Montego Bay, at $476 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 $476.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $855 on average.

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 January, when tickets cost $526 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $707 and $653 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, Sunday 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 Saturday, 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 6 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$123
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 25% 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.

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

    The cheapest time of day to fly to Jamaica is generally in the afternoon, when round-trip flights cost $287 on average. Morning departures are around 7% more expensive than evening flights, 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 $601.

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.

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 4278 reviews
8.6Crew
7.6Entertainment
8.0Comfort
8.2Boarding
7.1Food
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Spirit gets you there; it's no worse than any other aircraft, all things considered. (It's not like everyone else is such a hero). But - holy moses - do they nickel and dime you to absolutely every nickel - I was really expecting to have to pay to use the bathroom. And when the captain comes on with a 5 minute sales pitch about getting "points", that was like something on Bizarro world. Other than that, everyone else was professional and worked hard to get us from point A to point B. I'm not loving all the "self-service" stuff but there it is - just when the machines don't work you don't have anyone to talk to.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

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.

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