$163 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 3/12. 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
$241
American Airlines
Thu 5/7Mon 5/11
MBJ - ORD • Non-stop
Cheapest one-way
$163
Typical prices: $204-$400
United Airlines
Thu 3/12
MBJ - ORD • Non-stop
Top airlines
American Airlines
Most flights • 7 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, May 7 - Mon, May 11
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
$241American Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
7:00 pm - 11:51 am
ORD
-
MBJ
16h 51m
1 stop
$246American Airlines
Thu, May 7 - Mon, May 11
Southwest Logo
2:55 pm - 9:45 am
MBJ
-
ORD
18h 50m
2 stops
Southwest Logo
6:00 am - 1:25 pm
ORD
-
MBJ
7h 25m
1 stop
$261Southwest
Thu, May 7 - Mon, May 11
Southwest Logo
2:25 pm - 10:45 pm
MBJ
-
MDW
8h 20m
2 stops
Southwest Logo
9:15 pm - 1:25 pm
MDW
-
MBJ
16h 10m
2 stops
$261Southwest
Thu, May 7 - Mon, May 11
Delta Logo
2:40 pm - 9:09 pm
MBJ
-
MDW
6h 29m
1 stop
Delta Logo
6:30 am - 1:16 pm
MDW
-
MBJ
6h 46m
1 stop
$307Delta
Thu, May 7 - Mon, May 11
Spirit Airlines Logo
12:11 pm - 7:47 pm
KIN
-
ORD
7h 36m
1 stop
Spirit Airlines Logo
5:34 pm - 11:06 am
ORD
-
KIN
17h 32m
1 stop
$380Spirit Airlines
Thu, May 14 - Mon, May 18
Spirit Airlines Logo
12:11 pm - 7:47 pm
KIN
-
ORD
7h 36m
1 stop
Spirit Airlines Logo
1:40 pm - 11:06 am
ORD
-
KIN
21h 26m
2 stops
$396Spirit Airlines
Tue, May 19 - Mon, Aug 31
Air Canada Logo
3:05 pm - 9:05 am
KIN
-
ORD
18h 00m
1 stop
Air Canada Logo
8:40 pm - 1:55 pm
ORD
-
KIN
17h 15m
1 stop
$416Air Canada
Wed, May 13 - Tue, May 26
Air Canada Logo
3:05 pm - 12:17 pm
KIN
-
ORD
21h 12m
2 stops
Air Canada Logo
8:20 pm - 1:55 pm
ORD
-
KIN
17h 35m
1 stop
$419Air Canada
Wed, Apr 1 - Wed, Apr 8
Delta Logo
1:38 pm - 10:31 pm
MBJ
-
MDW
8h 53m
1 stop
Delta Logo
6:00 am - 3:28 pm
MDW
-
MBJ
9h 28m
1 stop
$487Delta
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 $290 one-way - $363 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 $132.

Good to know

Low seasonMarch
Cheapest flight$163
Best time to beat the crowds with an average 23% drop 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 $384. The cheapest price found on KAYAK in the last 2 weeks cost $249 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 $438. On the other hand, the most expensive day to fly is Monday, where prices are $640 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 $468 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 $498.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $290 or less one-way and $363 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 8204 reviews
7.9Comfort
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
Airline reviews

Boarding was efficient and smooth. Departure time was on time. Arrival to Detroit was early. Average food . Average crew service Very average cabin comfort. Nothing spectacular one way ir another, except for the excellent on time performance.

8.0 ExcellentAnonymous, Feb 2026
AMS - DTW
Read more Delta reviews

Boarding was efficient and smooth. Departure time was on time. Arrival to Detroit was early. Average food . Average crew service Very average cabin comfort. Nothing spectacular one way ir another, except for the excellent on time performance.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Awful - both legs. The check in was awful, getting on the plane required walking down a spiral staircase (dangerous), then taking a bus about 5 miles out from the terminal. The seat was broken (I was in business), there was no internet during the flight (both legs). The aircraft was very old. I saw rust in some place, tape holding things up in the bathroom. This was an unacceptable experience for such a long haul flight.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Flight from CHI to PVD was delayed by over 20 hours.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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

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
Griffith
Saint John

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.