$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 4/23. 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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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, Jun 4 - Tue, Oct 6
American Airlines Logo
2:23 pm - 7:10 pm
MBJ
-
ORD
4h 47mnonstop
American Airlines Logo
8:05 am - 12:06 pm
ORD
-
MBJ
4h 01mnonstop
$241American Airlines
Fri, May 15 - Sat, Sep 5
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
4:56 pm - 9:25 am
ORD
-
MBJ
16h 29m
1 stop
$246American Airlines
Fri, May 29 - Mon, Aug 31
American Airlines Logo
3:02 pm - 12:32 am
MBJ
-
ORD
9h 30m
1 stop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$252American Airlines
Fri, May 29 - Mon, Aug 31
American Airlines Logo
3:02 pm - 12:32 am
MBJ
-
ORD
9h 30m
1 stop
American Airlines Logo
5:20 am - 3:25 pm
ORD
-
MBJ
10h 05m
1 stop
$256American Airlines
Sat, Jul 4 - Sat, Aug 1
United Airlines Logo
4:33 pm - 10:20 am
MBJ
-
ORD
17h 47m
1 stop
United Airlines Logo
9:40 pm - 3:10 pm
ORD
-
MBJ
17h 30m
1 stop
$272United Airlines
Tue, Jun 2 - Tue, Sep 1
Spirit Airlines Logo
12:00 pm - 12:14 am
MBJ
-
ORD
12h 14m
1 stop
Spirit Airlines Logo
5:15 am - 11:01 am
ORD
-
MBJ
5h 46m
1 stop
$316Spirit Airlines
Mon, May 18 - Sun, May 31
Spirit Airlines Logo
12:00 pm - 8:03 am
MBJ
-
ORD
20h 03m
2 stops
Spirit Airlines Logo
5:05 am - 10:59 am
ORD
-
MBJ
5h 54m
1 stop
$333Spirit Airlines
Tue, Mar 10 - Fri, Mar 13
Copa Airlines Logo
12:20 pm - 1:04 am
MBJ
-
ORD
12h 44m
1 stop
Copa Airlines Logo
3:22 pm - 10:11 am
ORD
-
MBJ
18h 49m
1 stop
$338Copa Airlines
Thu, Apr 9 - Thu, Apr 16
Multiple Airlines Logo
12:32 pm - 10:50 pm
KIN
-
ORD
10h 18m
1 stop
Multiple Airlines Logo
1:27 pm - 11:06 am
ORD
-
KIN
21h 39m
1 stop
$345Multiple Airlines
Fri, May 29 - Mon, Aug 31
Multiple Airlines Logo
12:11 pm - 12:14 am
KIN
-
ORD
12h 03m
1 stop
Multiple Airlines Logo
7:20 am - 11:00 am
ORD
-
KIN
27h 40m
1 stop
$385Multiple 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 $277 one-way - $365 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 $141.

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 $385. 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 $439. 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 $277 or less one-way and $365 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 8242 reviews
7.2Food
8.5Crew
7.9Comfort
8.1Boarding
7.8Entertainment
Airline reviews

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

8.0 ExcellentSharon, Feb 2026
CVG - ATL
Read more Delta reviews

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Improve boarding- the zone assignment and boarding is always a mess- there is not clear instructions of what is going on at the gate. As a meme bet there is no more selection of a good seats when booking. Only offers middle seats to choose or pay extra. There is not more benefit with Amex no benefits at all.

alike schedule and times it’s very good for me, I will stay wad delta for ever

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

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

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
Munster
Schererville
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.