$199 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 $312per 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 $440 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 $440.

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 $462 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 $334.

Good to know

Cheapest flight

$199
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 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 $416. 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 10289 reviews
8.1Crew
6.7Food
7.3Comfort
7.7Boarding
7.1Entertainment
Airline reviews

We were delay because so many bags needed to be gate checked and it was disappointing not to have outlets in the seats for such a long flight.

6.0 GoodMargaret, Oct 2026
Read more United Airlines reviews

We were delay because so many bags needed to be gate checked and it was disappointing not to have outlets in the seats for such a long flight.

Raleigh to Chicago was OK. The problem was Chicago to Lincoln. Flight was delayed 4 hours. Give them credit for the updates and reason why it was delayed

Comfortable seats and good crew. There should be some breakfast options in menu for economy class to purchase Wifi was not working in the flight

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline much.

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.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

They lost my luggage and have ruined first day of my vacation. Still don’t have it. I have nothing. I also paid for a seat I did not get. They changed both our seats with no notice. Will never fly this airline again.

My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

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.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

Horrible airline, will never buy another ticket with the airline or Kayak. They close the gate 2 hours early in Kenya, I had to buy a new ticket and get a hotel room

It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.

Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.

There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.

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.

More options for your flight to Illinois

Complete your trip to Illinois with a hotel stay or car rental