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

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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?

The cheapest ticket to Illinois from Jamaica found in the last 5 days was to Chicago Midway Airport, at $375 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 $375.

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 $230 (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 $467 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 $471 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 $413.

Good to know

Cheapest flight

$209
Most popular time to fly and prices are also 20% 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 Friday, where round-trip prices are $548 on average.

Reviews of the top airlines flying 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.
7.3
United AirlinesOverall score based on 10388 reviews
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
6.7Food
Airline reviews

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

2.0 MediocreAnonymous, Oct 2026
Read more United Airlines reviews

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

Flight from Munich to O’Hare was great but it was on Lufthansa, a UA partner. It had more legroom than United, seat slid forward to make reclining more comfortable, they offered free drinks. United offered none of this. Oh and the food was superior to United’s which honestly, sucked.

Requested for warm or hot water because of throat pain, it was denied. The entertainment system was hung, requested the crew to turn it off, instead of turning it off they rebooted the device. It was stuck again, no one bothered to check.

Horrible on the chicago end. They change hates then there is a plane at the new gate so we can’t pull in. Then that plane has mechanical issue and needs to be pulled back to the gate but we can’t get to another new gate due the other plane being in the way. Horrible gate management which will cause many customers to miss connections.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

The employees seemed impatient with their guests. It seemed like they were giving us orders, instead of easily assisting. Our flight was delayed waiting on a flight attendant. It was alright.

My easiest trip ever. Flights left on time, and came in a few minutes early. The flights weren’t full so it was very comfortable. Thank you United

Quinoa chocolate cookies are my favorite! Would be nice to have internet service like American

Better management of the boarding process. Is there any way you could forward all the window seats first? That's the Way Reno Air used to do it, and they had the fastest boarding in the industry!

Old plane, no amenities. Very abrupt landing. Unnecessarily long taxi time.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

The flight from Chicago to Orlando was delayed inordinately. My whole journey from Lansing to MCO took 9.5 hours is just annoying and frustrating. We can understand the delays may be beyond their control, but overall the journey was so much waiting until reached to MCO. This is NOT the first time for me - but at least 80% of the time in this route. I barely remember reaching places on time.

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.

More options for your flight to Illinois

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