$161 Find Cheap Flights from Jamaica to Illinois

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KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Illinois, 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 Illinois, as well as popular online travel agencies
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KAYAK's insights & trends for flights to Illinois

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

What is the cheapest flight to Illinois?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to Illinois from Jamaica found in the last 72 hours was to Chicago Midway Airport, at $423 round-trip. The most popular route is Montego Bay (MBJ) to Chicago Midway Airport (MDW) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $423.

What is the cheapest month to fly from Jamaica to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Jamaica to Illinois, 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 Jamaica to Illinois is February, when tickets cost $408 (return) on average. On the other hand, the most expensive months are January and March, when the average cost of round-trip tickets is $566 and $542 respectively.

Which is the cheapest airport to fly into in Illinois?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $307.


Good to know

Low seasonFebruary
High seasonJune
Cheapest flight$161
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 3% 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 from Jamaica to Illinois 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 from Jamaica to Illinois 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 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 from Jamaica to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Wednesday where round-trip tickets can be as cheap as $416. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $615 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $501 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $509.

Top 5 airlines serving from Jamaica to Illinois

 
See real verified KAYAK customer reviews for airlines flying to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Jamaica to Illinois. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
8.0
SouthwestOverall score based on 4294 reviews
7.1Food
8.0Comfort
8.6Crew
7.6Entertainment
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

The flight overall was good but I believe giving back to the customers would be a plus. Not saying a big giving back but small is also acceptable like Wi-Fi (Free) or snacks(free). Just one would be good.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

My experience with Spirit airlines was terrible. We had a 5 hour delay going to Jamaica and about a 3.5 hour delay returning home with no explanation keep in mind there was already a 4 hour layover in addition to the delay on the return home . We should have arrived in Montego Bay at 1:30pm on 12/22/24 instead we did not get there until about 5 or 6pm our final destination was Negril which is about a 2 hour drive from the airport so we did not reach our hotel until after 8pm so we literally spun the entire day traveling. On 12/27/24 we headed back home. We had arrived in Fort Lauderdale around 4-4:30pm for our layover expecting to be fly from there a little after 9pm and get back to Philadelphia by 12:05am Saturday morning 12/28/24. Once at the airport we kept receiving emails every 15-30 minutes or so apologizing for a delay with the time pushed further and further back. We did not depart from Fort Lauderdale until 12:33am. I forgot to mention that I was traveling with my 5 year old son so if you have small children you already know how that went. The only compensation they gave was two 12 dollar meal vouchers one for my son and one for for myself that we were not able to use because by the time they sent them the places in the airport were mostly closed and we were finally boarding the plane. The staff were very unprofessional and were being rude when we asked them questions about why the time kept getting pushed back. This was my first and absolute last time traveling by way of Spirit airlines. I most absolutely will not ever travel Spirit again. By far the most terrible travel experience thus far.

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Book cheap flights from Jamaica to Illinois

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Illinois found on KAYAK in the last 72 hours.
5/24Sat
1 stopSpirit Airlines
11h 58mMBJ-ORD
5/29Thu
1 stopSpirit Airlines
15h 27mORD-MBJ
$300
6/3Tue
1 stopSpirit Airlines
10h 57mMBJ-ORD
6/10Tue
1 stopSpirit Airlines
5h 57mORD-MBJ
$302
6/14Sat
1 stopDelta
10h 30mKIN-ORD
6/21Sat
2 stopsDelta
12h 55mORD-KIN
$382
6/10Tue
2 stopsAmerican Airlines
13h 13mKIN-ORD
6/17Tue
2 stopsAmerican Airlines
11h 50mORD-KIN
$396
7/2Wed
1 stopAmerican Airlines
10h 17mMBJ-ORD
7/5Sat
1 stopAmerican Airlines
16h 41mORD-MBJ
$427
5/24Sat
nonstopUnited Airlines
4h 29mMBJ-ORD
5/29Thu
1 stopUnited Airlines
24h 46mORD-MBJ
$431
5/31Sat
1 stopDelta
9h 42mMBJ-MDW
6/8Sun
1 stopDelta
9h 25mMDW-MBJ
$462
5/31Sat
nonstopUnited Airlines
4h 29mMBJ-ORD
6/8Sun
nonstopUnited Airlines
4h 07mORD-MBJ
$523
6/9Mon
2 stopsSouthwest
10h 00mMBJ-MDW
6/12Thu
2 stopsSouthwest
15h 35mMDW-MBJ
$717
6/9Mon
nonstopSouthwest
4h 10mMBJ-MDW
6/12Thu
1 stopSouthwest
8h 50mMDW-MBJ
$747

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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 Illinois found on KAYAK in the last 72 hours.
5/29Thu
1 stopSpirit Airlines
11h 58mMBJ-ORD
$161
6/4Wed
1 stopSpirit Airlines
10h 57mMBJ-ORD
$175
5/22Thu
nonstopAmerican Airlines
4h 35mMBJ-ORD
$242
7/9Wed
nonstopAmerican Airlines
4h 34mMBJ-ORD
$249
7/9Wed
nonstopSouthwest
4h 10mMBJ-MDW
$249
6/15Sun
1 stopDelta
9h 49mKIN-ORD
$252
5/14Wed
1 stopSouthwest
7h 40mMBJ-MDW
$252
8/20Wed
1 stopDelta
8h 06mMBJ-ORD
$254
7/3Thu
1 stopUnited Airlines
24h 34mMBJ-ORD
$273
5/31Sat
nonstopUnited Airlines
4h 29mMBJ-ORD
$318

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Last minute flights to Illinois

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 Illinois that are departing in the next 10 days.
5/3Sat
multi-stopJetBlue
12h 11mMBJ-ORD
7/31Thu
multi-stopJetBlue
9h 06mORD-MBJ
$443
5/2Fri
nonstopAmerican Airlines
4h 35mMBJ-ORD
5/7Wed
nonstopAmerican Airlines
4h 00mORD-MBJ
$450
5/2Fri
nonstopAmerican Airlines
4h 35mMBJ-ORD
5/7Wed
multi-stopAmerican Airlines
8h 35mORD-MBJ
$454
5/2Fri
multi-stopDelta
7h 45mMBJ-ORD
5/7Wed
multi-stopDelta
5h 53mORD-MBJ
$455
5/2Fri
multi-stopSpirit Airlines
11h 19mKIN-ORD
5/7Wed
multi-stopSpirit Airlines
17h 43mORD-KIN
$486
5/2Fri
multi-stopDelta
10h 00mKIN-ORD
5/8Thu
multi-stopDelta
12h 50mORD-KIN
$489
5/2Fri
multi-stopSpirit Airlines
11h 19mKIN-ORD
5/8Thu
multi-stopSpirit Airlines
7h 24mORD-KIN
$530
5/2Fri
multi-stop
22h 42mKIN-ORD
5/6Tue
multi-stop
14h 40mORD-KIN
$618
5/3Sat
multi-stop
33h 03mMBJ-ORD
7/31Thu
multi-stop
18h 28mORD-MBJ
$735
5/2Fri
multi-stopAir Canada
23h 53mMBJ-ORD
5/7Wed
multi-stopAir Canada
19h 40mORD-MBJ
$1,642

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Everything you need to know for your flight to Illinois

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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