$165 Find Cheap Flights from Jamaica to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, 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 Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$294
Overall average: $477
Spirit Airlines
Thu 12/11Sun 12/14
MBJ - ORD • 1 stop
Cheapest non-stop
$320
Typical prices: $496-$595
American Airlines
Thu 12/11Sun 12/14
MBJ - ORD • Non-stop
Top airlines
American Airlines
Most flights • 19 per week
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jamaica to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jamaica to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jamaica to Chicago

Thu, Dec 11 - Sun, Dec 14
Spirit Airlines Logo
1:05 pm - 12:09 amMBJ-ORD
12h 04m1 stop
Spirit Airlines Logo
5:00 am - 12:10 pmORD-MBJ
6h 10m1 stop
$294Spirit Airlines
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Thu, Dec 11 - Sun, Dec 14
Spirit Airlines Logo
1:05 pm - 9:48 pmMBJ-ORD
9h 43m2 stops
Spirit Airlines Logo
5:00 am - 12:10 pmORD-MBJ
6h 10m1 stop
$309Spirit Airlines
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Thu, Dec 11 - Sun, Dec 14
American Airlines Logo
3:12 pm - 6:59 pmMBJ-ORD
4h 47mnonstop
American Airlines Logo
8:10 am - 1:20 pmORD-MBJ
4h 10mnonstop
$320American Airlines
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Wed, Dec 3 - Wed, Dec 10
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$324United Airlines
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Thu, Dec 11 - Sun, Dec 14
American Airlines Logo
3:12 pm - 6:59 pmMBJ-ORD
4h 47mnonstop
American Airlines Logo
5:00 am - 2:47 pmORD-MBJ
8h 47m1 stop
$325American Airlines
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Wed, Dec 3 - Wed, Dec 10
Delta Logo
2:29 pm - 10:43 pmMBJ-ORD
9h 14m1 stop
Delta Logo
6:45 am - 2:13 pmORD-MBJ
6h 28m1 stop
$326Delta
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Fri, Dec 12 - Fri, Jan 2
United Airlines Logo
3:36 pm - 11:32 pmMBJ-ORD
8h 56m1 stop
United Airlines Logo
9:15 pm - 4:12 pmORD-MBJ
17h 57m1 stop
$330United Airlines
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Wed, Dec 31 - Sat, Jan 10
Multiple Airlines Logo
1:05 pm - 6:39 pmMBJ-ORD
6h 34m1 stop
Multiple Airlines Logo
5:05 am - 3:46 pmORD-MBJ
9h 41m1 stop
$357Multiple Airlines
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Thu, Dec 11 - Thu, Dec 18
Multiple Airlines Logo
1:05 pm - 8:01 pmMBJ-ORD
7h 56m1 stop
Multiple Airlines Logo
6:00 am - 2:29 pmORD-MBJ
7h 29m1 stop
$379Multiple Airlines
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Wed, Dec 10 - Wed, Dec 17
Delta Logo
3:38 pm - 11:47 pmMBJ-MDW
9h 09m1 stop
Delta Logo
5:29 pm - 11:09 amMDW-MBJ
16h 40m1 stop
$402Delta
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Booking Insights

KAYAK's insights & trends for flights to Chicago

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

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Montego Bay $234 one-way - $344 round-trip.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport, with an average flight price of $148.

Good to know

Low seasonFebruary
Cheapest flight$170
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Montego Bay to Chicago Midway Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $388. The cheapest price found on KAYAK in the last 2 weeks cost $189 and departed from Montego Bay Sangster Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as $441. On the other hand, the most expensive day to fly is Monday, where prices are $620 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    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 to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    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 to Chicago 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 to Chicago?

    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 to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to Chicago is generally in the evening, when flights cost $454 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $501.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $234 or less one-way and $344 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airlines flying from Jamaica to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Jamaica to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? 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.
7.9
DeltaOverall score based on 8001 reviews
8.2Boarding
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

I truly love flying with Delta. They have always treated me with the upmost respect

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

Seats comfortable, service and food very mediocre, staff not very attentive, worse than many other our flights with Delta.

Overall good experience; however, there was one flight attendant who was rather rough compared to everyone else. Everything else was good: entertainment, food. Delta keeps on delivering! Thank you!

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

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