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$181 Find cheap flights from Jamaica to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/22. 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
Wed 6/12
Wed 6/19

Search hundreds of travel sites at once for deals on flights to Chicago

 
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 41,771,603 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago 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 clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $401. On the other hand, the most expensive day to fly is Monday, where prices are $564 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, 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 is April, where tickets cost $299 on average for one-way flights. On the other hand, the most expensive months are January and February, where the average cost of tickets from Jamaica is $709 and $541 respectively. For return trips, the best month to travel is April with an average price of $299.

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

The average price for all flights to Chicago 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 is generally in the afternoon, when flights cost $404 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $481.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Montego Bay $228 one-way - $357 round-trip.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, 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 28 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of $101.

Which airlines fly to Chicago?

American Airlines, Southwest and United Airlines are the most frequent flyers to Chicago from Jamaica. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,878 per week, followed by American Airlines with 4,329 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 77% of all flights arriving there.

How long is the flight to Chicago?

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 are there each day?

There are around 2,002 direct flights from within Jamaica to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 50% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 14,010 direct flights from within Jamaica to Chicago. The most common day for departures is Thursday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago 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. Instead, there are 17 medium-haul flights (3-6 hour flight duration), with the most arriving from Montego Bay.

How many cities have direct flights to Chicago?

From Jamaica, there are direct flights to Chicago from 1 city. This city is Montego Bay and there are 17 direct flights each week.

Good to know

Low season

January

High season

May

Cheapest flight

$181
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Montego Bay to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $380. The cheapest price found on KAYAK in the last 2 weeks cost $207 and departed from Montego Bay Sangster Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 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?

    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 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

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

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Jamaica to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Jamaica

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 4 airlines serving from Jamaica to Chicago

 
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 Chicago? 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 10736 reviews
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
8.0Entertainment
Airline reviews

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

10.0 ExcellentSash, May 2024SEA - HNL
Read more about Delta reviews

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

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

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.
6/6Thu
1 stopSpirit Airlines
12h 09mMBJ-ORD
6/10Mon
1 stopSpirit Airlines
6h 36mORD-MBJ
$265
6/6Thu
1 stopSpirit Airlines
12h 09mMBJ-ORD
6/10Mon
2 stopsSpirit Airlines
19h 32mORD-MBJ
$298
6/9Sun
nonstopAmerican Airlines
4h 30mMBJ-ORD
6/23Sun
nonstopAmerican Airlines
4h 05mORD-MBJ
$357
7/18Thu
nonstopAmerican Airlines
4h 30mMBJ-ORD
7/28Sun
nonstopAmerican Airlines
4h 00mORD-MBJ
$420
7/7Sun
1 stopFrontier
10h 27mMBJ-ORD
8/3Sat
1 stopFrontier
7h 46mORD-MBJ
$464
6/6Thu
1 stopDelta
7h 36mMBJ-MDW
6/10Mon
2 stopsDelta
18h 01mMDW-MBJ
$473
5/25Sat
nonstopUnited Airlines
4h 24mMBJ-ORD
6/14Fri
1 stopUnited Airlines
17h 55mORD-MBJ
$482
6/6Thu
2 stopsDelta
18h 23mMBJ-MDW
6/10Mon
2 stopsDelta
18h 01mMDW-MBJ
$511
5/25Sat
nonstopUnited Airlines
4h 24mMBJ-ORD
6/14Fri
nonstopUnited Airlines
4h 00mORD-MBJ
$528
5/25Sat
2 stopsFrontier
16h 02mMBJ-MDW
6/14Fri
1 stopFrontier
8h 08mMDW-MBJ
$638

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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.
5/22Wed
2 stops
17h 56mMBJ-ORD
$181
6/26Wed
1 stopSpirit Airlines
10h 07mMBJ-ORD
$192
5/22Wed
1 stopFrontier
20h 25mMBJ-ORD
$196
8/8Thu
1 stopFrontier
10h 27mMBJ-ORD
$217
6/10Mon
1 stopSpirit Airlines
12h 29mKIN-ORD
$218
5/24Fri
nonstopAmerican Airlines
4h 30mMBJ-ORD
$221
5/24Fri
1 stopUnited Airlines
8h 58mMBJ-ORD
$231
7/27Sat
1 stopDelta
12h 19mMBJ-ORD
$256
5/22Wed
2 stopsDelta
14h 41mMBJ-ORD
$262
6/17Mon
2 stopsAmerican Airlines
19h 05mMBJ-ORD
$279

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Last minute flights to Chicago

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.
5/15Wed
nonstopAmerican Airlines
4h 30mMBJ-ORD
9/2Mon
nonstopAmerican Airlines
4h 00mORD-MBJ
$357
5/15Wed
nonstopAmerican Airlines
4h 30mMBJ-ORD
9/4Wed
multi-stopAmerican Airlines
8h 04mORD-MBJ
$362
5/15Wed
multi-stopSpirit Airlines
10h 51mMBJ-ORD
9/4Wed
multi-stopSpirit Airlines
6h 41mORD-MBJ
$371
5/17Fri
multi-stopUnited Airlines
15h 42mMBJ-ORD
5/21Tue
multi-stopUnited Airlines
6h 18mORD-MBJ
$372
5/15Wed
nonstopAmerican Airlines
4h 30mMBJ-ORD
9/2Mon
multi-stopAmerican Airlines
10h 45mORD-MBJ
$445
5/17Fri
multi-stopSpirit Airlines
10h 05mMBJ-ORD
5/31Fri
multi-stopSpirit Airlines
18h 18mORD-MBJ
$446
5/15Wed
multi-stopAmerican Airlines
20h 40mMBJ-ORD
9/2Mon
multi-stopAmerican Airlines
16h 38mORD-MBJ
$455
5/17Fri
multi-stop
20h 28mKIN-ORD
5/20Mon
multi-stop
14h 00mORD-KIN
$544
5/17Fri
multi-stop
25h 34mKIN-ORD
5/20Mon
multi-stop
16h 45mORD-KIN
$560
5/17Fri
multi-stopUnited Airlines
21h 48mMBJ-ORD
5/22Wed
multi-stopUnited Airlines
6h 18mORD-MBJ
$617

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Flights to Chicago

Return flight deals:

Chicago - Jamaica

Cabin classes:

$1,151
$2,633
$330

Popular routes

The most searched flights to Chicago by KAYAK users.