$104 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 2/3. 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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1 adult, Economy, 0 bags

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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$377
Kingston
Kingston1 stop$333
Montego Bay
Montego Baynonstop$377
Kingston
Kingston1 stop$333

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

Mon, Jan 26 - Fri, Jan 30
Spirit Airlines Logo
5:15 am - 12:12 pm
ORD
-
KIN
5h 57m1 stop
Spirit Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m1 stop
$333Spirit Airlines
Mon, Feb 9 - Thu, Feb 19
Spirit Airlines Logo
5:15 am - 12:12 pm
ORD
-
KIN
5h 57m1 stop
Spirit Airlines Logo
1:17 pm - 11:47 pm
KIN
-
ORD
11h 30m1 stop
$337Spirit Airlines
Wed, Feb 18 - Sun, Feb 22
Spirit Airlines Logo
4:43 pm - 12:15 pm
ORD
-
KIN
18h 32m1 stop
Spirit Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m1 stop
$351Spirit Airlines
Mon, Jan 12 - Thu, Jan 15
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$377American Airlines
Sat, Jan 24 - Thu, Jan 29
American Airlines Logo
5:26 pm - 12:24 pm
ORD
-
MBJ
17h 58m1 stop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$381American Airlines
Sun, Jan 18 - Wed, Jan 21
Delta Logo
6:45 am - 3:20 pm
MDW
-
MBJ
7h 35m1 stop
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
$435Delta
Fri, Feb 27 - Thu, Mar 5
Delta Logo
6:20 pm - 12:32 pm
MDW
-
MBJ
17h 12m2 stops
Delta Logo
4:44 pm - 12:46 pm
MBJ
-
MDW
21h 02m2 stops
$440Delta
Sun, Feb 15 - Sat, Feb 21
Frontier Logo
9:04 pm - 9:00 am
MDW
-
MBJ
10h 56m1 stop
Frontier Logo
10:40 am - 9:33 pm
MBJ
-
MDW
11h 53m1 stop
$443Frontier
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 9:00 pm
MBJ
-
MDW
8h 00m1 stop
$463Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m2 stops
$468Southwest
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 $406 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 $406.

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 $507, 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 January, when tickets cost $532 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $686 and $685 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 Friday 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 11 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$104
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 7% 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 $602.

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 4253 reviews
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

4.0 OkayChad, Dec 2025
BNA - PNS
Read more Southwest reviews

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

First time in a decade I threw up on the flight, turbulence was terrible!! The staff were kinda rude at times.

Boarding was good, clearly explained and efficient. Staff were helpful, I would've liked a place to get coffee that wasn't Starbucks

The most horrible flight ever not only Spirit delayed our flight 2 hours departure time for a 1 hour flight — that I could have driven FLL to TPA and spend less time on the road —- and they did the same on the return with 2-hr delay again!!! Then to top all, the rubber like and most unconfortable seats in the industry with no leg room!!! There should be an award for these kinds of companies measuring % of returning customers!!!

The flight was cancelled and Spirit said they could not rebook me on another flight for six days. They said they couldn't do anything for another six days.

Flight was on time, Newark staff, especially Nathan, very helpful, and plane crew to RDU very good without being pushy. We arrived early, and had a gentle landing.

See my last comment for the first leg. That should’ve been in here

Horrible. Arrived at my gate at 6:37 for a 6:50 flight and was denied by staff to board. Literally watched my flight leave from the window and it didn’t take off until after 7am. Tried to talk to staff and they were rude beyond compare. Will never fly with this airline again.

Our flight got rescheduled 48 hours later, the airline didn’t pay a penny for our expenses.

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

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.