$160 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 1/29. 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
$239
Spirit Airlines
พฤ. 2/19พฤ. 2/26
MBJ - ORD • 1 stop
Cheapest non-stop
$381
American Airlines
พฤ. 2/5พ. 2/25
MBJ - ORD • Non-stop
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Flight Deals
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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

พฤ., ก.พ. 19 - พฤ., ก.พ. 26
Spirit Airlines Logo
1:00 pm - 9:13 pm
MBJ
-
ORD
9h 13m1 stop
Spirit Airlines Logo
8:16 pm - 12:02 pm
ORD
-
MBJ
14h 46m1 stop
$239Spirit Airlines
พฤ., ก.พ. 5 - พ., ก.พ. 25
Spirit Airlines Logo
12:57 pm - 7:38 pm
MBJ
-
ORD
7h 41m1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$245Spirit Airlines
พฤ., ก.พ. 5 - พ., ก.พ. 18
Multiple Airlines Logo
1:17 pm - 10:36 pm
KIN
-
ORD
10h 19m1 stop
Multiple Airlines Logo
4:43 pm - 12:15 pm
ORD
-
KIN
18h 32m1 stop
$315Multiple Airlines
จ., ก.พ. 23 - พฤ., ก.พ. 26
Multiple Airlines Logo
1:17 pm - 9:13 pm
KIN
-
ORD
8h 56m1 stop
Multiple Airlines Logo
3:21 pm - 12:15 pm
ORD
-
KIN
19h 54m1 stop
$323Multiple Airlines
พฤ., ก.พ. 5 - พ., ก.พ. 25
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
American Airlines Logo
7:10 am - 2:18 pm
ORD
-
MBJ
6h 08m1 stop
$346American Airlines
ส., พ.ค. 16 - ส., พ.ค. 30
Delta Logo
9:00 am - 11:55 pm
KIN
-
ORD
14h 55m1 stop
Delta Logo
7:10 am - 8:05 pm
ORD
-
KIN
12h 55m2 stops
$401Delta
พ., พ.ค. 13 - อ., พ.ค. 26
American Airlines Logo
2:27 pm - 10:58 pm
KIN
-
ORD
8h 31m1 stop
American Airlines Logo
8:15 am - 7:39 pm
ORD
-
KIN
11h 24m1 stop
$410American Airlines
พฤ., ก.พ. 19 - พฤ., ก.พ. 26
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m1 stop
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
$421Delta
พฤ., เม.ย. 9 - พฤ., พ.ค. 14
Southwest Logo
2:25 pm - 11:40 pm
MBJ
-
MDW
9h 15m1 stop
Southwest Logo
7:10 am - 1:55 pm
MDW
-
MBJ
6h 45m1 stop
$515Southwest
พฤ., เม.ย. 9 - พฤ., พ.ค. 14
Southwest Logo
2:25 pm - 11:40 pm
MBJ
-
MDW
9h 15m1 stop
Southwest Logo
9:15 pm - 11:35 am
MDW
-
MBJ
14h 20m2 stops
$520Southwest
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 $213 one-way - $452 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 $165.

Good to know

Low seasonFebruary
Cheapest flight$160
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Montego Bay to Chicago O'Hare 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 $392. The cheapest price found on KAYAK in the last 2 weeks cost $213 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 $432. On the other hand, the most expensive day to fly is Monday, where prices are $562 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 $499.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $213 or less one-way and $452 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 8017 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.9Comfort
8.5Crew
Airline reviews

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

6.0 GoodJason, Jan 2026
BOS - SFO
Read more Delta reviews

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

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

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.