$204 Find Cheap Flights from Jamaica to Chicago - Compare and Save

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 12/17. 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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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

Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
9:00 am - 1:12 pm
ORD
-
MBJ
4h 12mnonstop
$321American Airlines
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
5:00 am - 4:08 pm
ORD
-
MBJ
11h 08m
1 stop
$326American Airlines
Wed, Sep 23 - Mon, Sep 28
Delta Logo
1:14 pm - 8:55 pm
MBJ
-
ORD
7h 41m
1 stop
Delta Logo
5:30 am - 3:34 pm
ORD
-
MBJ
10h 04m
1 stop
$327Delta
Wed, Sep 23 - Mon, Sep 28
United Airlines Logo
12:52 pm - 9:00 am
MBJ
-
ORD
20h 08m
1 stop
United Airlines Logo
7:52 pm - 11:43 am
ORD
-
MBJ
15h 51m
1 stop
$331United Airlines
Sat, Aug 22 - Mon, Aug 24
Delta Logo
4:59 pm - 11:57 pm
MBJ
-
ORD
6h 58m
1 stop
Delta Logo
5:30 am - 3:34 pm
ORD
-
MBJ
10h 04m
1 stop
$428Delta
Mon, Nov 23 - Sun, Nov 29
United Airlines Logo
3:36 pm - 11:42 pm
MBJ
-
ORD
9h 06m
1 stop
United Airlines Logo
8:42 am - 1:46 pm
ORD
-
MBJ
4h 04mnonstop
$429United Airlines
Sat, Jul 18 - Sat, Jul 25
JetBlue Logo
12:08 pm - 11:44 pm
KIN
-
ORD
11h 36m
1 stop
JetBlue Logo
7:00 am - 5:18 pm
ORD
-
KIN
10h 18m
1 stop
$478JetBlue
Sat, Aug 1 - Sat, Aug 29
Frontier Logo
1:32 pm - 11:07 am
MBJ
-
MDW
21h 35m
1 stop
Frontier Logo
11:45 am - 12:17 pm
MDW
-
MBJ
24h 32m
1 stop
$484Frontier
Thu, Jul 16 - Tue, Jul 21
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
$505Frontier
Wed, Jul 15 - Sat, Jul 25
JetBlue Logo
12:08 pm - 11:44 pm
KIN
-
ORD
11h 36m
1 stop
JetBlue Logo
2:35 pm - 9:17 pm
ORD
-
KIN
6h 42m
1 stop
$516JetBlue
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 the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $401. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $533 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago is April, where tickets cost $146 on average for return flights. On the other hand, the most expensive months are January and February, where the average cost of tickets from Jamaica is $397 and $365 respectively. For one-way flights, the best month to travel is February with an average price of $158.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally in the evening, when round-trip 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 $459.

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 $301 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 (RFD), with an average flight price of $126.

Find deals

Good to know

Low seasonJuly
Cheapest flight$204
Best time to beat the crowds with an average 8% drop 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 $430. The cheapest price found on KAYAK in the last 2 weeks cost $198 and departed from Montego Bay Sangster Intl Airport.

  • 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.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $274 or less one-way and $301 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 airline 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.
7.1
American AirlinesOverall score based on 11746 reviews
6.8Entertainment
6.4Food
7.9Crew
7.5Boarding
7.2Comfort
Airline reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

6.0 GoodHardin, Jun 2026
ICT - ORD
Read more American Airlines reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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
Schererville
Munster
Chesterton
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.
First Class flights to Chicago
Business Class flights to Chicagofrom $1,091
Premium Economy Class flights to Chicagofrom $1,268
Economy Class flights to Chicagofrom $229