$170 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 11/23. 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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Everything you should know

Cheapest round-trip
$320
Typical prices: $528-$603
American Airlines
Fri 1/16Mon 1/19
MBJ - ORD • Non-stop
Cheapest one-way
$170
Typical prices: $217-$289
Spirit Airlines
Sun 11/23
MBJ - ORD • 1 stop
Top airlines
American Airlines
Most flights • 14 per week
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to Chicago!
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

Fri, Jan 16 - Mon, Jan 19
American Airlines Logo
1:58 pm - 5:37 pmMBJ-ORD
4h 39mnonstop
American Airlines Logo
10:07 am - 3:20 pmORD-MBJ
4h 13mnonstop
$320American Airlines
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Fri, Dec 5 - Fri, Dec 12
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
9:08 pm - 2:05 pmORD-MBJ
15h 57m1 stop
$323United Airlines
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Fri, Jan 16 - Mon, Jan 19
Delta Logo
8:00 am - 4:39 pmMBJ-ORD
9h 39m1 stop
Delta Logo
5:50 am - 12:40 pmORD-MBJ
5h 50m1 stop
$326Delta
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Fri, Jan 16 - Mon, Jan 19
Delta Logo
12:35 pm - 9:46 pmMBJ-MDW
10h 11m1 stop
Delta Logo
6:00 am - 8:25 pmMDW-MBJ
13h 25m1 stop
$326Delta
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Wed, Nov 12 - Wed, Nov 19
Spirit Airlines Logo
1:06 pm - 12:27 amKIN-ORD
12h 21m1 stop
Spirit Airlines Logo
5:10 am - 12:01 pmORD-KIN
5h 51m1 stop
$334Spirit Airlines
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Sat, Nov 22 - Mon, Nov 24
Multiple Airlines Logo
1:07 pm - 11:29 pmMBJ-ORD
11h 22m1 stop
Multiple Airlines Logo
6:35 pm - 12:02 pmORD-MBJ
16h 27m2 stops
$342Multiple Airlines
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Sat, Nov 22 - Mon, Nov 24
Spirit Airlines Logo
1:07 pm - 11:29 pmMBJ-ORD
11h 22m1 stop
Spirit Airlines Logo
3:43 pm - 12:02 pmORD-MBJ
19h 19m1 stop
$361Spirit Airlines
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Tue, Mar 3 - Wed, Mar 4
JetBlue Logo
11:55 am - 9:33 pmKIN-ORD
10h 38m1 stop
JetBlue Logo
7:00 am - 4:13 pmORD-KIN
8h 13m1 stop
$409JetBlue
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Fri, Jan 16 - Mon, Jan 19
JetBlue Logo
2:00 pm - 1:10 pmMBJ-ORD
24h 10m2 stops
JetBlue Logo
8:45 am - 6:53 pmORD-MBJ
9h 08m1 stop
$420JetBlue
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Wed, Nov 19 - Mon, Nov 24
Multiple Airlines Logo
2:40 pm - 8:00 amMBJ-ORD
18h 20m2 stops
Multiple Airlines Logo
6:00 am - 3:15 pmORD-MBJ
8h 15m1 stop
$438Multiple Airlines
Find Deal
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 $217 one-way - $293 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 $136.

Good to know

Low seasonFebruary
Cheapest flight$170
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 5% 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 $351. The cheapest price found on KAYAK in the last 2 weeks cost $203 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 Saturday where tickets can be as cheap as $422. On the other hand, the most expensive day to fly is Monday, where prices are $642 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 $446 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 $500.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $217 or less one-way and $293 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 7981 reviews
8.2Boarding
7.9Entertainment
8.5Crew
7.9Comfort
7.3Food
Airline reviews

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

6.0 GoodDavid, Oct 2025LAX - JFK
Read more Delta reviews

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

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

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

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
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.

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