$125 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Jamaica departing on 5/4. 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, 0 bags

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Cheap Flights from O'Hare Intl to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$314
Kingston
Kingston1 stop$403
Montego Bay
Montego Bay1 stop$314
Kingston
Kingston1 stop$403

Book Cheap O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to Jamaica

Mon, Apr 27 - Wed, May 6
American Airlines Logo
9:45 am - 3:37 pm
ORD
-
MBJ
5h 52m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$314American Airlines
Mon, May 4 - Fri, May 8
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$318American Airlines
Sun, Apr 12 - Thu, Apr 16
Spirit Airlines Logo
6:10 pm - 11:05 am
ORD
-
MBJ
16h 55m
1 stop
Spirit Airlines Logo
1:21 pm - 12:24 am
MBJ
-
ORD
11h 03m
1 stop
$321Spirit Airlines
Mon, May 4 - Fri, May 8
American Airlines Logo
8:50 pm - 2:15 pm
ORD
-
MBJ
17h 25m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$322American Airlines
Tue, Apr 14 - Tue, Apr 28
Spirit Airlines Logo
5:05 am - 11:05 am
ORD
-
MBJ
6h 00m
1 stop
Spirit Airlines Logo
1:21 pm - 12:24 am
MBJ
-
ORD
11h 03m
1 stop
$326Spirit Airlines
Mon, May 4 - Fri, May 8
United Airlines Logo
8:45 am - 3:10 pm
ORD
-
MBJ
6h 25m
1 stop
United Airlines Logo
4:12 pm - 11:44 pm
MBJ
-
ORD
7h 32m
1 stop
$332United Airlines
Wed, May 13 - Wed, May 20
Multiple Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
Multiple Airlines Logo
3:05 pm - 9:05 am
KIN
-
ORD
18h 00m
1 stop
$443Multiple Airlines
Wed, May 13 - Wed, May 20
Multiple Airlines Logo
5:05 am - 2:12 pm
ORD
-
KIN
9h 07m
1 stop
Multiple Airlines Logo
3:05 pm - 7:45 am
KIN
-
ORD
16h 40m
2 stops
$444Multiple Airlines
Wed, May 13 - Wed, May 20
Air Canada Logo
6:21 pm - 1:55 pm
ORD
-
KIN
43h 34m
2 stops
Air Canada Logo
3:05 pm - 12:11 pm
KIN
-
ORD
21h 06m
2 stops
$469Air Canada
Thu, May 14 - Thu, May 21
Air Canada Logo
1:55 pm - 1:55 pm
ORD
-
KIN
24h 00m
2 stops
Air Canada Logo
11:35 am - 7:25 pm
KIN
-
ORD
7h 50m
1 stop
$473Air Canada
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Jamaica flights

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

What is the cheapest Chicago O'Hare Intl Airport 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 O'Hare Intl Airport found in the last 72 hours was to Montego Bay, at $277 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 $277.

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

The average price for all round-trip flights from Chicago O'Hare Intl Airport 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 $571 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 $571.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Jamaica is October, when tickets cost $493 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $736 and $591 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Jamaica?

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

Your flight ticket price will generally be cheaper if you fly to Jamaica on a Tuesday and more expensive on a Thursday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Wednesday, and avoid Mondays for better deals.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Jamaica, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$125
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 40% increase in price.
Flight from Chicago O'Hare Airport to Montego Bay

FAQs - booking Jamaica flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport to Jamaica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from O'Hare Intl to Jamaica

 
Need help choosing which airline to fly with from O'Hare Intl 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
DeltaOverall score based on 8303 reviews
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

2.0 MediocreJaka, Mar 2026
MSP - SEA
Read more Delta reviews

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

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.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

Smooth flight staff very friendly and we arrived 15 mins earlier

I was in the airport when I'll check the status of my flight and it was canceled and without any reason. The worst of the worst ...

I never had an opportunity to experience them! They cancelled my flight TWICE!!!

Return flight was canceled. Needed to reschedule with another airline the next day. Cost an an additional $84. At another airport 45 miles further away

Spent seven hours in the airport with spirit pushing he flight time back two hours every two hours only to then have it canceled without explanation. The employees said, “They’ve been doing this for the last five days.” Would have been great if they told us to expect that when we arrived.

Seat do not reclined and tight space. Flight changed so many times hard to keep up.

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.

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

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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 !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

Everything you need to know for your flight from O'Hare Intl to Jamaica

Information on your arrival and departure airports