$157 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 2/24. 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
$265
Overall average: $566
Spirit Airlines
Thu 1/15Sun 1/18
MBJ - ORD • 1 stop
Cheapest non-stop
$340
Typical prices: $491-$641
American Airlines
Thu 1/15Sun 1/18
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, Jan 15 - Sun, Jan 18
Spirit Airlines Logo
12:57 pm - 9:03 pm
MBJ
-
ORD
9h 06m1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$265Spirit Airlines
Sun, Dec 21 - Sun, Jan 4
Spirit Airlines Logo
1:05 pm - 12:30 am
MBJ
-
ORD
12h 25m1 stop
Spirit Airlines Logo
5:00 am - 12:05 pm
ORD
-
MBJ
6h 05m1 stop
$308Spirit Airlines
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
12:57 pm - 8:57 pm
MBJ
-
ORD
9h 00m1 stop
Multiple Airlines Logo
8:51 pm - 12:02 pm
ORD
-
MBJ
14h 11m2 stops
$332Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
$340American Airlines
Thu, Jan 15 - Sun, Jan 18
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
American Airlines Logo
7:30 pm - 12:58 pm
ORD
-
MBJ
16h 28m1 stop
$345American Airlines
Wed, Jan 21 - Wed, Jan 28
Delta Logo
2:19 pm - 11:56 pm
MBJ
-
ORD
10h 37m1 stop
Delta Logo
7:05 am - 3:20 pm
ORD
-
MBJ
7h 15m1 stop
$346Delta
Wed, Jan 21 - Wed, Jan 28
Delta Logo
12:38 pm - 10:22 pm
MBJ
-
MDW
10h 44m1 stop
Delta Logo
6:00 am - 12:54 pm
MDW
-
MBJ
5h 54m1 stop
$346Delta
Wed, Jan 21 - Wed, Jan 28
American Airlines Logo
1:58 pm - 11:27 pm
MBJ
-
ORD
10h 29m2 stops
American Airlines Logo
6:54 am - 3:16 pm
ORD
-
MBJ
7h 22m1 stop
$359American Airlines
Thu, Apr 16 - Mon, Apr 20
United Airlines Logo
1:51 pm - 6:20 pm
MBJ
-
ORD
4h 29mnonstop
United Airlines Logo
8:50 am - 3:10 pm
ORD
-
MBJ
6h 20m1 stop
$422United Airlines
Wed, Jan 21 - Wed, Jan 28
Multiple Airlines Logo
2:55 pm - 11:46 pm
KIN
-
ORD
33h 51m3 stops
Multiple Airlines Logo
5:53 pm - 12:12 pm
ORD
-
KIN
17h 19m2 stops
$615Multiple 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 $251 one-way - $387 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 $172.

Good to know

Low seasonFebruary
Cheapest flight$157
Best time to beat the crowds but there is an average 18% 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 $347. The cheapest price found on KAYAK in the last 2 weeks cost $212 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 $431. On the other hand, the most expensive day to fly is Monday, 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 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 $498.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $251 or less one-way and $387 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 8011 reviews
7.9Entertainment
7.3Food
7.9Comfort
8.1Boarding
8.5Crew
Airline reviews

The food is terrible. The staff is wonderful. Comfort is good.

10.0 ExcellentRonda, Dec 2025
JAX - JFK
Read more Delta reviews

The food is terrible. The staff is wonderful. Comfort is good.

For some reason, I couldn't choose my seat. The airline gave me a seat when I got there. Not happy about that. Otherwise, everything else was great!

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

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.