Jamaica

$158+ Cheap flights from Chicago (CHI) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Jul 17 — Jul 241
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Cheap flight deals from Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 17, 2026.

This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:00 am
ORD
-
MBJ
1 stop10h 33m
JetBlue
Mon 8/3112:55 pm
MBJ
-
ORD
1 stop10h 49m
JetBlue
Deal found 6/15$355
This Cheapflightsfares deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
ORD
-
MBJ
1 stop10h 33m
JetBlue
Tue 8/2512:55 pm
MBJ
-
ORD
1 stop10h 49m
JetBlue
Deal found 6/13$369
This JetBlue deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Wed 11/112:00 pm
MBJ
-
ORD
1 stop10h 44m
JetBlue
Deal found 6/15$374
This Super.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Wed 11/113:59 pm
MBJ
-
ORD
1 stop8h 45m
JetBlue
Deal found 6/15$382
This JetBlue deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am
ORD
-
MBJ
1 stop6h 54m
JetBlue
Thu 11/123:59 pm
MBJ
-
ORD
1 stop8h 45m
JetBlue
Deal found 6/16$384
This Super.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:00 am
ORD
-
MBJ
1 stop7h 47m
JetBlue
Tue 12/82:45 pm
MBJ
-
ORD
1 stop9h 59m
JetBlue
Deal found 6/17$391
This FlightHub deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am
ORD
-
MBJ
1 stop6h 48m
JetBlue
Tue 11/32:00 pm
MBJ
-
ORD
1 stop10h 44m
JetBlue
Deal found 6/14$399
This FlightHub deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
ORD
-
MBJ
1 stop7h 47m
JetBlue
Sat 12/121:00 pm
MBJ
-
ORD
1 stop11h 44m
JetBlue
Deal found 6/16$409
This Cheapflightsfares deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am
ORD
-
KIN
1 stop5h 43m
JetBlue
Wed 10/283:55 pm
KIN
-
ORD
1 stop7h 49m
JetBlue
Deal found 6/15$451
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
-
MBJ
1 stop6h 22m
Frontier
Wed 8/121:32 pm
MBJ
-
MDW
1 stop8h 31m
Frontier
Deal found 6/16$452
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:00 am
ORD
-
KIN
1 stop14h 53m
American Airlines
Thu 6/256:22 am
KIN
-
ORD
1 stop15h 38m
American Airlines
Deal found 6/14$456
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORD
-
KIN
1 stop10h 42m
American Airlines
Sun 8/236:05 am
KIN
-
ORD
1 stop17h 25m
American Airlines
Deal found 6/13$461

Find flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated June 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$355
(Super.com)

One-way from

$158
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$583

Good round-trip deal

$450 or less

Good one-way deal

$148 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
From Chicago (CHI) to Jamaica
One-way flight from Chicago (CHI) to Jamaica
Highest demand for flights based on searches. 0% potential increase in price ($5 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in June 2026
Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
Price to beat on a one-way flight from Chicago (CHI) to Jamaica.

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 17, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 8/31

7:00 am-5:06 pm

1 stop10h 06m

Kingston Norman Manley

Wed 9/2

1:56 pm-11:44 pm

1 stop9h 48m

$456

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 7/22

7:00 am-5:18 pm

1 stop10h 18m

Kingston Norman Manley

Tue 7/28

12:08 pm-11:44 pm

1 stop11h 36m

$466

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 7/18

8:02 am-10:11 am

1 stop26h 09m

Montego Bay Sangster Intl

Fri 7/24

11:16 am-12:01 am

1 stop12h 45m

$468

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 9/4

10:54 am-8:13 pm

1 stop9h 19m

Kingston Norman Manley

Sun 9/13

9:00 am-9:46 pm

1 stop12h 46m

$524

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 8/15

6:05 am-8:13 pm

1 stop14h 08m

Kingston Norman Manley

Tue 8/25

9:13 am-10:36 pm

1 stop13h 23m

$524

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 9/4

9:54 am-8:13 pm

1 stop10h 19m

Kingston Norman Manley

Sun 9/13

9:00 am-8:27 pm

1 stop11h 27m

$524

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 7/30

5:30 am-8:04 pm

1 stop14h 34m

Kingston Norman Manley

Wed 8/5

9:13 am-8:55 pm

1 stop11h 42m

$524

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 7/17

2:35 pm-11:37 pm

1 stop9h 02m

Kingston Norman Manley

Fri 7/24

12:08 pm-11:44 pm

1 stop11h 36m

$532

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

6:40 am-1:01 pm

1 stop6h 21m

Montego Bay Sangster Intl

Thu 8/20

4:59 pm-7:56 am

2 stops14h 57m

$533

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 7/25

8:02 am-11:15 am

1 stop27h 13m

Montego Bay Sangster Intl

Tue 7/28

12:22 pm-1:57 pm

1 stop25h 35m

$560

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

Currently, December is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $84). Flying from Chicago to Jamaica in September is currently the most expensive (average of $238). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 17, 2026.

When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How far ahead should I book a flight from Chicago to Jamaica?

Booking 58 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Jamaica. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated June 17, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Chicago to Jamaica?

    A quick flight from Chicago to Jamaica can take about 9h 19m. JetBlue provides one of the quickest options available for as low as $524. There are 1769 mi between Chicago and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Jamaica one-way?

    One-way options have recently been found by users for as low as $108 on Frontier. Other airlines that offer cheap prices include American Airlines from $138 and United Airlines from $138 one-way.

  • What are the most popular routes from Chicago to Jamaica?

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $402 for a flight from Chicago to Jamaica. The cheapest flight overall is $137 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $355.

  • Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

    Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.

  • Can I find deals for business class flights from Chicago to Jamaica?

    Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Jamaica?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $84). Flying from Chicago to Jamaica in September is currently the most expensive (average of $238). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 6 airlines flying from Chicago to Jamaica

Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$715FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$599FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$297Average$510FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$297Average$520FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$318Average$645FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$467Average$653FlexibilityNo cancel feeOn-time63%

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