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Find cheap flights from Jamaica to Chicago O'Hare Airport from $163

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 6/8. 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
0 bags
dom. 6/9
dom. 6/16

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,895,468 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Flights to O'Hare Intl - Travel Insights & Trends

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

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as $400. On the other hand, the most expensive day to fly is Monday, where prices are $579 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago O'Hare Intl Airport, 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 to Chicago O'Hare Intl Airport is August, where tickets cost $362 on average for one-way flights. On the other hand, the most expensive months are November and June, where the average cost of tickets from Jamaica is $658 and $493 respectively. For return trips, the best month to travel is August with an average price of $362.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The average price for all flights to Chicago O'Hare Intl Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, when flights cost $384 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $419.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From Montego Bay $220 one-way - $357 round-trip.

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 17 days before departure.

Which airline offers the most flights to Chicago O'Hare Intl Airport?

Of the 12 airlines that fly to Chicago O'Hare Intl Airport, United Airlines offers the most flights, with around 5,149 per week, followed by American Airlines with 4,284 flights per week.

How long is the flight to Chicago O'Hare Intl Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Montego Bay, which takes 4h 27m, and Kingston, which takes 9h 28m.

How many direct flights to Chicago O'Hare Intl Airport are there each day?

There are around 1,539 direct flights from within Jamaica to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

How many direct flights to Chicago O'Hare Intl Airport are there each week?

Each week there are around 10,773 direct flights from within Jamaica to Chicago O'Hare Intl Airport. The most common day for departures is Monday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago O'Hare Intl Airport each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago O'Hare Intl Airport. Instead, there are 10 medium-haul flights (3-6 hour flight duration), with the most arriving from Montego Bay.

How many cities have direct flights to Chicago O'Hare Intl Airport?

From Jamaica, there are direct flights to Chicago O'Hare Intl Airport from 1 city. This city is Montego Bay and there are 10 direct flights each week.

Good to know

Low season

October

High season

May

Cheapest flight

$163
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 5% increase in price.
Flight from Montego Bay to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport flights

  • How far is Chicago O'Hare Airport from central Chicago?

    The distance between Chicago O'Hare Airport and downtown Chicago is 16 miles.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $372. The cheapest price found on KAYAK in the last 2 weeks cost $205 and departed from Montego Bay Sangster Intl Airport.

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

    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 to Chicago O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago O'Hare Airport?

    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 to Chicago O'Hare Airport 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 to Chicago O'Hare Airport?

    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 to Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago O'Hare Airport flight deals.

Prefer to fly non-stop to Chicago O'Hare Intl?

Find which airlines fly direct to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Jamaica to Chicago O'Hare Intl

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Jamaica

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights
See more direct flights

Top 4 airlines serving from Jamaica to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Jamaica to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to O'Hare Intl? 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
DeltaOverall score based on 10768 reviews
7.9Comfort
8.2Boarding
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

Book cheap flights from Jamaica to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
6/6jue.
1 stopSpirit Airlines
12h 29mKIN-ORD
6/10lun.
1 stopSpirit Airlines
16h 38mORD-KIN
$303
5/21mar.
1 stopSpirit Airlines
10h 44mMBJ-ORD
5/28mar.
1 stopSpirit Airlines
6h 41mORD-MBJ
$307
6/8sáb.
1 stopSpirit Airlines
10h 27mKIN-ORD
6/15sáb.
1 stopSpirit Airlines
16h 38mORD-KIN
$315
6/6jue.
1 stopSpirit Airlines
12h 29mKIN-ORD
6/10lun.
2 stopsSpirit Airlines
14h 21mORD-KIN
$317
6/6jue.
1 stopSpirit Airlines
12h 29mKIN-ORD
6/13jue.
1 stopSpirit Airlines
16h 38mORD-KIN
$338
7/18jue.
nonstopAmerican Airlines
4h 30mMBJ-ORD
7/28dom.
nonstopAmerican Airlines
3h 55mORD-MBJ
$420
7/18jue.
nonstopAmerican Airlines
4h 30mMBJ-ORD
7/28dom.
1 stopAmerican Airlines
15h 10mORD-MBJ
$423
5/25sáb.
nonstopUnited Airlines
4h 24mMBJ-ORD
6/14vie.
1 stopUnited Airlines
17h 55mORD-MBJ
$425
5/22mié.
2 stops
12h 25mMBJ-ORD
5/25sáb.
1 stop
16h 03mORD-MBJ
$426
5/25sáb.
nonstopUnited Airlines
4h 24mMBJ-ORD
6/14vie.
nonstopUnited Airlines
4h 00mORD-MBJ
$477

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
6/8sáb.
1 stopSpirit Airlines
10h 07mMBJ-ORD
$163
5/17vie.
1 stopFrontier
30h 17mMBJ-ORD
$198
5/18sáb.
1 stopFrontier
8h 17mMBJ-ORD
$200
5/22mié.
nonstopAmerican Airlines
4h 30mMBJ-ORD
$221
5/22mié.
1 stopUnited Airlines
7h 18mMBJ-ORD
$231
5/17vie.
2 stops
27h 18mMBJ-ORD
$240
5/22mié.
2 stops
12h 25mMBJ-ORD
$243
5/22mié.
2 stopsDelta
17h 15mMBJ-ORD
$262
5/15mié.
2 stopsAmerican Airlines
20h 40mMBJ-ORD
$281
8/17sáb.
2 stopsDelta
17h 02mMBJ-ORD
$334

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Last minute flights to O'Hare Intl

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
5/11sáb.
multi-stopSpirit Airlines
11h 03mKIN-ORD
5/14mar.
multi-stopSpirit Airlines
16h 45mORD-KIN
$722
5/11sáb.
multi-stop
21h 00mKIN-ORD
5/14mar.
multi-stop
19h 25mORD-KIN
$767
5/11sáb.
multi-stop
21h 00mKIN-ORD
5/14mar.
multi-stop
17h 49mORD-KIN
$889
5/11sáb.
multi-stopSpirit Airlines
26h 23mKIN-ORD
5/14mar.
multi-stopSpirit Airlines
17h 49mORD-KIN
$1,025

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Flights to Chicago O'Hare Airport

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Jamaica

Cabin classes:

$1,151
$2,633
$330

Popular routes

The most searched flights to Chicago O'Hare Airport by KAYAK users.