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Jamaica

$111+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Apr 5 — Apr 121
Sa 4/5
Sa 4/12
1 adult, Economy
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Cheap flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated März 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$346
(Booking.com)

One-way from

$111
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$666

Good round-trip deal

$533 or less

Good one-way deal

$217 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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From Chicago (CHI) to Jamaica
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One-way flight from Chicago (CHI) to Jamaica
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Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
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Price to beat on a one-way flight from Chicago (CHI) to Jamaica.
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Find 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 März 31, 2025.

This Booking.com deal was found by Cheapflights users on 3/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 5/145:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Mi 5/211:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
Deal found 3/30$346
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Mi 5/147:00 amORD - KIN
2 stops12h 40mAmerican Airlines
Mi 5/216:30 amKIN - ORD
2 stops10h 59mAmerican Airlines
Deal found 3/30$437
This Delta deal was found by Cheapflights users on 3/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/2812:48 pmMDW - KIN
1 stop7h 12mDelta
Mo 5/59:00 amKIN - MDW
1 stop8h 59mDelta
Deal found 3/29$443
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 5/149:39 amORD - KIN
1 stop10h 21mDelta
Mi 5/219:00 amKIN - ORD
1 stop8h 11mDelta
Deal found 3/30$443
This Booking.com deal was found by Cheapflights users on 3/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/246:15 pmORD - KIN
2 stops42h 20mMultiple Airlines
Sa 5/311:34 pmKIN - ORD
1 stop10h 31mMultiple Airlines
Deal found 3/30$461
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/277:47 amORD - MBJ
2 stops27h 15mMultiple Airlines
Sa 5/313:05 pmMBJ - ORD
1 stop9h 00mMultiple Airlines
Deal found 3/30$462
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 9/217:10 amORD - MBJ
1 stop8h 23mDelta
Mi 10/11:12 pmMBJ - ORD
1 stop8h 00mDelta
Deal found 3/30$463
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 9/36:00 amMDW - MBJ
1 stop9h 36mDelta
Mi 9/101:12 pmMBJ - MDW
1 stop8h 32mDelta
Deal found 3/30$463
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Do 5/154:50 pmORD - MBJ
1 stop19h 04mAmerican Airlines
Do 5/222:25 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Deal found 3/31$464
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/48:45 amORD - MBJ
1 stop6h 25mUnited Airlines
Fr 4/111:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Deal found 3/30$465
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/246:20 amMDW - MBJ
1 stop26h 00mFrontier
Sa 5/318:55 amMBJ - MDW
1 stop13h 22mFrontier
Deal found 3/30$465
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Do 5/17:33 pmORD - MBJ
1 stop15h 22mSpirit Airlines
Mo 5/512:00 pmMBJ - ORD
1 stop12h 58mSpirit Airlines
Deal found 3/31$469

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 März 31, 2025.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Chicago

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mi 5/14

5:05 am-12:29 pm

1 stop7h 24m

Kingston Norman Manley

Mi 5/21

1:34 pm-11:04 pm

1 stop9h 30m

$346

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mi 5/14

7:00 am-7:40 pm

2 stops12h 40m

Kingston Norman Manley

Mi 5/21

6:30 am-5:29 pm

2 stops10h 59m

$437

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mo 4/28

12:48 pm-8:00 pm

1 stop7h 12m

Kingston Norman Manley

Mo 5/5

9:00 am-5:59 pm

1 stop8h 59m

$443

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mi 5/14

9:39 am-8:00 pm

1 stop10h 21m

Kingston Norman Manley

Mi 5/21

9:00 am-5:11 pm

1 stop8h 11m

$443

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sa 5/24

6:15 pm-12:35 pm

2 stops42h 20m

Kingston Norman Manley

Sa 5/31

1:34 pm-12:05 am

1 stop10h 31m

$461

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Di 5/27

7:47 am-11:02 am

2 stops27h 15m

Montego Bay Sangster Intl

Sa 5/31

3:05 pm-12:05 am

1 stop9h 00m

$462

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

So 9/21

6:00 am-12:58 pm

1 stop6h 58m

Montego Bay Sangster Intl

Fr 9/26

4:58 pm-11:53 pm

1 stop6h 55m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mi 9/3

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

Mi 9/10

1:12 pm-9:44 pm

1 stop8h 32m

$463

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Do 5/15

4:50 pm-11:54 am

1 stop19h 04m

Montego Bay Sangster Intl

Do 5/22

2:25 pm-7:00 pm

Nonstop4h 35m

$464

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sa 5/24

6:20 am-8:20 am

1 stop26h 00m

Montego Bay Sangster Intl

Sa 5/31

8:55 am-10:17 pm

1 stop13h 22m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 38 results
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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, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $569). 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 März 31, 2025.

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.

What is the cheapest day to fly from Chicago to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Jamaica. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Jamaica flight should consider departing on Sunday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Jamaica

Explore weekly flight availability from Chicago to Jamaica. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated März 31, 2025.

The most flights from CHI to JM0 are scheduled on a Sunday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 März 31, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines from Chicago to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,400 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
SWISS
7.5
Good
1,570 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,614 reviews
Southwest
8.0
Very good
4,275 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

  • 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 $111 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $183 and Frontier from $191 one-way.

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

    The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $434 for a flight from Chicago to Jamaica. The cheapest flight overall is $196 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $301.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $569). 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

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Alternative routes for Chicago to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
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O'Hare Intl to Ponce flights
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Midway to Providenciales flights
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St. Louis to Providenciales flights
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Moline to Montego Bay flights
O'Hare Intl to Port of Spain flights
Midway to George Town flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Basseterre flights
O'Hare Intl to The Valley flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Road Town flights
St. Louis to Simpson Bay flights
O'Hare Intl to Kralendijk flights
Moline to Punta Cana flights
O'Hare Intl to Freeport flights

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 März 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$205Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$273Average$440FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$679FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$393Average$696FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$393Average$610FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$579Average$735FlexibilityNo cancel feeOn-time63%
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