$207 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 $233 (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 $490 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 $477 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

$207
Most popular time to fly and prices are also 19% 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 Tuesday where round-trip tickets can be as cheap as $449. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $562 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 10441 reviews
7.1Entertainment
6.7Food
7.7Boarding
8.1Crew
7.3Comfort
Airline reviews

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

4.0 OkayJoseph, Oct 2026
Read more United Airlines reviews

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

The first leg of my trip the Republic Airlines aircraft was late due to a maintenance problem. Then I called United to reroute. Their reroute airline lost my bag but found it and returned it two days later. Hopefully my return trip home is better.

There was not even a single time where united airlines from lga has made to the gate straight , 1 hr if delay today

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.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

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

More options for your flight to Illinois

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