$149 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 2/11. 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
$306
American Airlines
Fri 2/20Mon 3/2
MBJ - ORD • 1 stop
Cheapest non-stop
$295
American Airlines
Wed 3/4Wed 3/11
MBJ - ORD • Non-stop
Top airlines
American Airlines
Most flights • 12 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

Fri, Feb 20 - Mon, Mar 2
American Airlines Logo
3:53 pm - 12:55 am
MBJ
-
ORD
10h 02m
1 stop
American Airlines Logo
8:20 am - 1:26 pm
ORD
-
MBJ
4h 06mnonstop
$306American Airlines
Fri, Feb 20 - Mon, Mar 2
American Airlines Logo
3:53 pm - 12:55 am
MBJ
-
ORD
10h 02m
1 stop
American Airlines Logo
5:00 am - 12:21 pm
ORD
-
MBJ
6h 21m
1 stop
$310American Airlines
Wed, May 6 - Sun, May 10
Southwest Logo
2:25 pm - 9:25 pm
MBJ
-
MDW
7h 00m
1 stop
Southwest Logo
5:15 am - 2:20 pm
MDW
-
MBJ
9h 05m
1 stop
$310Southwest
Fri, Feb 20 - Mon, Mar 2
Multiple Airlines Logo
1:00 pm - 9:13 pm
MBJ
-
ORD
9h 13m
1 stop
Multiple Airlines Logo
6:04 pm - 12:30 pm
ORD
-
MBJ
41h 26m
2 stops
$347Multiple Airlines
Wed, May 6 - Sun, May 10
Southwest Logo
12:15 pm - 9:50 pm
MBJ
-
MDW
9h 35m
2 stops
Southwest Logo
5:15 am - 2:20 pm
MDW
-
MBJ
9h 05m
1 stop
$361Southwest
Mon, Apr 13 - Tue, Apr 21
Multiple Airlines Logo
1:57 pm - 10:39 pm
MBJ
-
ORD
8h 42m
1 stop
Multiple Airlines Logo
1:55 pm - 11:35 am
ORD
-
MBJ
21h 40m
2 stops
$374Multiple Airlines
Tue, Mar 24 - Tue, Apr 14
Spirit Airlines Logo
12:00 pm - 7:46 pm
MBJ
-
ORD
7h 46m
1 stop
Spirit Airlines Logo
8:41 pm - 11:02 am
ORD
-
MBJ
14h 21m
1 stop
$384Spirit Airlines
Mon, Apr 13 - Tue, Apr 21
American Airlines Logo
1:15 pm - 5:58 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
8:10 am - 12:15 pm
ORD
-
MBJ
4h 05mnonstop
$394American Airlines
Tue, Mar 24 - Tue, Apr 14
Delta Logo
11:15 am - 6:53 pm
MBJ
-
ORD
7h 38m
1 stop
Delta Logo
7:00 am - 3:29 pm
ORD
-
MBJ
8h 29m
2 stops
$405Delta
Sat, Mar 14 - Tue, Mar 31
Spirit Airlines Logo
12:17 pm - 7:46 pm
KIN
-
ORD
7h 29m
1 stop
Spirit Airlines Logo
5:05 am - 11:00 am
ORD
-
KIN
5h 55m
1 stop
$410Spirit Airlines
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 $256 one-way - $315 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 $115.

Good to know

Low seasonMarch
Cheapest flight$149
Best time to beat the crowds with an average 24% drop in price.
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 $404. 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 $438. On the other hand, the most expensive day to fly is Friday, where prices are $557 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 afternoon, when flights cost $499 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $507.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $256 or less one-way and $315 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 8076 reviews
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
7.9Comfort
Airline reviews

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

8.0 ExcellentAnonymous, Jan 2026
ORF - ATL
Read more Delta reviews

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

My requested wheelchair never appeared. So many entertainment choices yet, I found little of interest and no internet option to search on my own. Both were minor issues.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

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

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.

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.