$209 Find Cheap Flights from Jamaica to Illinois - Compare and Save

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Cheap Flights from Jamaica to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Chicago
4h 26mNonstop
from $368per person
Booking Insights

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?

The cheapest ticket to Illinois from Jamaica found in the last 5 days was to Chicago Midway Airport, at $415 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 5 days was $415.

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

The cheapest month for flights from Jamaica to Illinois is December, when tickets cost $232 (return) on average. On the other hand, the most expensive months are August and January, when the average cost of round-trip tickets is $500 and $445 respectively.

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

The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost $461 on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $486.

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 $329.

Good to know

Cheapest flight

$209
Most popular time to fly with an average 8% increase in price.
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 Thursday where round-trip tickets can be as cheap as $402. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $547 on average.

Reviews of the top 3 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.
7.4
United AirlinesOverall score based on 10254 reviews
6.7Food
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
Airline reviews

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

8.0 ExcellentAnonymous, Sep 2026
Read more United Airlines reviews

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The price. Omg $1100. Was crazy and it was not clear on the website.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

After having bad experience last time This time they were very good

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

The counter person at the gate was rude and demeaning, to the point that I wouldn't fly this airline again.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Flight was delayed 3 hours. No food on plane besides snacks

Every thing went smooth. No complaints except deplaning could have been quicker

I was grossly overcharged to change my return flight. Had to do it through Kayak because it was booked that way and I was not given the fare price listed at the time on JetBlue or kayak. Was traveling with another couple that booked directly through JetBlue and they paid the $100 change fee and the difference between what they paid originally(same as me) and the displayed fares and it was less than $400 total for two tickets. I paid almost $700 to change the same fare tickets they purchased and had to pay again for upgraded seat selection that I previously paid for on top of the almost $700 increase. Difficult to talk to the kayak representative because of his accent. Told me I had to wait for confirmation to be sure it had been changed and that I could take up to a few hours. The call itself after the wait time took almost 30 minutes, which could’ve been done directly on JetBlue in 2 to 3 minutes.. My husband and I were given separate boarding zones. They would not let us board together. I had to board in the last zone. They made me check my bag even though my husband told me that he had a spot to put my carry-on. Since he boarded before me. The flight crew tried to accommodate, but the woman that was boarding in the terminal came down and would not let me take my carry-on. She was aggressive, rude and condescending to everybody in line and told them she was being audited. When I told her that my husband had secured a spot for me to put my carry-on with his backpack, that would then move to under the seat. She told me that she couldn’t play favorites, although I was second to last to board the plane since my boarding zone was changed. They told me because I forwarded my husband his ticket that’s what separated our boarding zones, but would not allow us to board together. The volume on my TV would not work, and my upgraded seat would not go into the fully upright position so I was told repeatedly during takeoff and landing to put my chair into the upright position which was embarrassing and uncomfortable to be told assertively so many times. I will not book through kayak again.

Nice plane, with TV, comfortable seats and leg room. Updated regularly on time changes

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

The boarding gate experience was good, however they were too exact at checking

Right now I’m still in Jamaica waiting on a flight to New York which I should be in New York from the 30th and I’m here in Jamaica

Ground crew gave me interference about carrying a laptop and a small shoulder bag, even though I told them I traveled with them all the time. I then placed my laptop bag in my carryon and took out a medical device, and ground crew still tried to give interference. I had to remind them that medical devices don't count towards luggage limits. It was quite annoying and unne

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

On-time departure, smooth ride for sure. All was good except, once again, there was no movies/TV as it wasn’t functioning.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

My experience was fine, with one surprising exception. After leveling off at cruising altitude, the main cabin flight attendant made an announcement that he had a cold, so he would not be coming through the aisle to provide cabin service. He claimed this was in consideration of his health and safety and ours. However, if passengers wanted a beverage, he invited them to come to the back of he plane, where he would provide service. I understand that a flight attendant's primary responsibility is to ensure passenger safety, but a secondary role is to provide service. If this flight attendant was too sick to perform his duties - and if he truly cared about passenger health and safety , as he claimed - he should have stayed home and called in sick, rather than exposing the cabin to his germs.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

We waited over 30 minutes for a gate in Chicago and more than 15 minutes for the doors to open. Cookies were missing from the menu.

Flight was 2 hr late but at least I was upgraded to first class

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

We were stuck with no gate upon landing for 90 minutes. Unacceptable.

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

I've never seen such poor lack of information at a gate station in 69 years. The flight from COS was to depart at 12:37pm. At boarding time, the gate agent in the microphone mumbled something completely unintelligible. I understood one word. "mechanical". Nothing else. Absolutely nothing else was reported for the next 1-1/2 hours. Past the time for departure, at 12:37pm, the gate agent simply walked away and the station was left unattended, as all of the passengers waited expectantly. The board still said that the flight was ON TIME. That was hard to believe since it was then well past 12:37pm and we all were sitting at the gate and there was absolutely no gate agent anywhere in site. I stopped an employee who was standing somewhere else and said that we can use some information. Much later, the same gate agent said that he will have information for us about 5 minutes but he "doesn't know any more than you do." Of course, five minutes came and went and he did absolutely nothing. One and a half hours after 12:37pm, he opened the door and began boarding. No explanation, no apology. Once we were boarded, the same happened on the plane. We sat. No explanation, no apology, from any flight attendants. Finally, finally, a pilot apologized and explained that there would be a delay. WELL NO KIDDING !

More options for your flight to Illinois

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