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Find cheap flights from Jamaica to Illinois from $181

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jamaica to Illinois 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

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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 for booking flights from Jamaica to Illinois

  • How does KAYAK find such low prices on flights from Jamaica to Illinois?

    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 Jamaica to Illinois.

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

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

    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 Illinois with an airline and back to Jamaica with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jamaica to Illinois?

    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 Illinois from Jamaica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Jamaica to Illinois

 
Need help choosing which airline to fly with from Jamaica to Illinois? 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
Caribbean AirlinesOverall score based on 186 reviews
7.6Comfort
6.7Entertainment
6.7Food
8.2Boarding
8.3Crew
Airline reviews

There was no music on the flights unless you came with your headset.

10.0 Excellentsusan, Apr 2024MIA - POS
Read more about Caribbean Airlines reviews

There was no music on the flights unless you came with your headset.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

It was good but the food was small for the duration of the flight.

I wrote to the entertainment and food OK because it was non-applicable All excellent

Checking in online still requires going on the physical check in line

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

The captain was great he made jokes and make thebflight very comfortable. Alerted us about the islands we flew over and Yolandra and her team took great care of us, very personable.

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.

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Rouge needs to offer seats with better pitch in economy. Many sick people on a full flight.

Overall, I would have to say my experience with Air Canada was mediocre their DC tens. Need to be updated not comfortable at all. Only one out of my four flights was decent. The staffing was very nice. Going through customs in Montreal was quick and easy. Air Canada has room for improvement with their facilities.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

My experience was pretty frustrating because the first leg of my flight on United (though booked through Air Canada) was delayed causing me to miss my connecting flight on Air Canada. This could have been an easy solve as there was a direct flight later that morning via Air Canada that they easily could have put me on which would have only gotten me to my destination 2 1/2 hours later but because United and Air Canada don’t seem to have good communication they gave me the run around both telling me to talk with the other which I did three times to no avail. I ended up taking the delayed flight and getting on a new connecting flight which ended up getting me to my destination 6 hours later and I missed the event I was planning to go to this evening.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

I was appalled to have to pay for just a regular seat when I went to book 24 hrs before my flight! Because it was only an hour flight I didn’t choose a seat from Grand Junction to Denver, but I did for Toronto and had to pay just to choose a regular available seat! In my 60+ years of flying this was the first time I have heard of this. Also, allowing people to bring on “huge “ suitcases, not carry on size, but much bigger, and then a large pack pack stuffed. So they take up all the room in the overhead bins and if we are later boarding, there is no room so we have to check our small carry on. I have already paid for and checked in one bag! I certainly will not choose to fly with United again unless it is the “only” airline available!

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

Pros: "Ok crew and good enough planes. I was on a short flight, so I didn’t mind. Just know what you are getting, budget airlines with little or no service."
Cons: "too many to list"

Book cheap flights from Jamaica to Illinois

Recent round-trip flight deals

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
6/11Tue
1 stopSpirit Airlines
9h 32mKIN-ORD
6/18Tue
1 stopSpirit Airlines
16h 38mORD-KIN
$303
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
6/6Thu
2 stopsDelta
18h 23mMBJ-MDW
6/10Mon
2 stopsDelta
18h 01mMDW-MBJ
$511
5/25Sat
2 stopsFrontier
16h 02mMBJ-MDW
6/14Fri
1 stopFrontier
8h 08mMDW-MBJ
$638
7/7Sun
1 stopJetBlue
14h 40mKIN-ORD
8/3Sat
1 stopJetBlue
8h 37mORD-KIN
$1,024

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Recent one-way flight deals

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
6/17Mon
2 stopsAmerican Airlines
19h 05mMBJ-ORD
$279
6/24Mon
1 stopAir Canada
7h 34mMBJ-ORD
$403
6/17Mon
2 stopsAir Canada
18h 48mMBJ-ORD
$678

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Last minute flights to Illinois

Last minute flight, train and bus deals

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 Illinois

Return flight deals:

Illinois - Jamaica

Cabin classes:

$1,151
$2,633
$330