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Jamaica

$117+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Chicago to Jamaica

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Jamaica (JM0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$277
(Mytrip)

One-way from

$117
(Cheapflightsfares)

Good round-trip deal

$518 or less

Good one-way deal

$236 or less
From Chicago (CHI) to Jamaica
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One-way flight from Chicago (CHI) to Jamaica
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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 enero 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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.
mié. 3/57:42 pmORD - KIN
1 stop16h 46mSpirit Airlines
mié. 3/121:36 pmKIN - ORD
1 stop10h 31mSpirit Airlines
Deal found 1/20$277
This American Airlines deal was found by Cheapflights users on 1/19. 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.
dom. 2/237:09 pmORD - KIN
1 stop16h 16mAmerican Airlines
jue. 2/276:00 amKIN - ORD
2 stops10h 41mAmerican Airlines
Deal found 1/19$366
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/2712:59 pmORD - KIN
2 stops22h 22mMultiple Airlines
mié. 3/52:36 pmKIN - ORD
1 stop10h 31mMultiple Airlines
Deal found 1/20$392
This FlightHub deal was found by Cheapflights users on 1/21. 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.
mar. 2/257:13 pmORD - MBJ
2 stops17h 30mSpirit Airlines
lun. 3/32:48 pmMBJ - ORD
1 stop10h 10mSpirit Airlines
Deal found 1/21$397
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/86:30 pmMDW - MBJ
1 stop18h 31mFrontier
lun. 5/122:21 pmMBJ - MDW
1 stop9h 18mFrontier
Deal found 1/21$403
This Frontier deal was found by Cheapflights users on 1/21. 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.
vie. 4/256:30 amORD - MBJ
1 stop6h 31mFrontier
lun. 4/282:21 pmMBJ - ORD
1 stop8h 50mFrontier
Deal found 1/21$407
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/185:22 pmORD - MBJ
2 stops17h 40mMultiple Airlines
mar. 3/253:05 pmMBJ - ORD
1 stop9h 02mMultiple Airlines
Deal found 1/21$416
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/246:48 pmMDW - KIN
2 stops16h 33mMultiple Airlines
mié. 2/263:30 pmKIN - MDW
1 stop21h 40mMultiple Airlines
Deal found 1/19$436
This American Airlines deal was found by Cheapflights users on 1/21. 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.
lun. 2/249:30 amORD - MBJ
Nonstop4h 05mAmerican Airlines
jue. 2/273:37 pmMBJ - ORD
Nonstop4h 40mAmerican Airlines
Deal found 1/21$456
This United Airlines deal was found by Cheapflights users on 1/21. 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.
mié. 2/266:00 amORD - MBJ
1 stop7h 37mUnited Airlines
mié. 3/52:48 pmMBJ - ORD
Nonstop4h 22mUnited Airlines
Deal found 1/21$461
This Southwest deal was found by Cheapflights users on 1/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/69:05 amMDW - MBJ
Nonstop4h 00mSouthwest
mié. 4/912:00 pmMBJ - MDW
1 stop7h 50mSouthwest
Deal found 1/21$476
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 3/255:45 amORD - MBJ
1 stop6h 15mDelta
jue. 3/277:00 amMBJ - ORD
1 stop9h 20mDelta
Deal found 1/21$481

Find flights from Chicago to Jamaica within your budget

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

mié. 3/5

7:42 pm-1:28 pm

1 stop16h 46m

Kingston Norman Manley

mié. 3/12

1:36 pm-12:07 am

1 stop10h 31m

$277

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

dom. 2/23

7:09 pm-12:25 pm

1 stop16h 16m

Kingston Norman Manley

jue. 2/27

6:00 am-3:41 pm

2 stops10h 41m

$366

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

jue. 2/27

12:59 pm-12:21 pm

2 stops22h 22m

Kingston Norman Manley

mié. 3/5

2:36 pm-12:07 am

1 stop10h 31m

$392

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 2/25

7:13 pm-1:43 pm

2 stops17h 30m

Montego Bay Sangster Intl

lun. 3/3

2:48 pm-11:58 pm

1 stop10h 10m

$397

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jue. 5/8

6:30 pm-1:01 pm

1 stop18h 31m

Montego Bay Sangster Intl

lun. 5/12

2:21 pm-11:39 pm

1 stop9h 18m

$403

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

vie. 4/25

6:30 am-1:01 pm

1 stop6h 31m

Montego Bay Sangster Intl

lun. 4/28

2:21 pm-11:11 pm

1 stop8h 50m

$407

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 3/25

5:22 pm-11:02 am

2 stops17h 40m

Montego Bay Sangster Intl

mar. 4/1

3:05 pm-9:29 am

1 stop18h 24m

$409

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

lun. 2/24

6:48 pm-12:21 pm

2 stops16h 33m

Kingston Norman Manley

mié. 2/26

3:30 pm-12:10 pm

1 stop21h 40m

$436

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 2/24

9:30 am-2:35 pm

Nonstop4h 05m

Montego Bay Sangster Intl

jue. 2/27

3:37 pm-7:17 pm

Nonstop4h 40m

$456

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 4/6

9:05 am-1:05 pm

Nonstop4h 00m

Montego Bay Sangster Intl

mié. 4/9

12:00 pm-7:50 pm

1 stop7h 50m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 35 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.

Travel insights for flights from Chicago to Jamaica

Get recent, data-driven insights about flights from Chicago to Jamaica including ideal travel times, pricing trends, and more.

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 enero 21, 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.

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 enero 21, 2025.

The most flights from CHI to JM0 are scheduled on a Saturday (4 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 enero 21, 2025.
See what other customers who have flown with United Airlines, Delta and Spirit 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
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $117 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $154 and American Airlines from $212 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 $742 for a flight from Chicago to Jamaica. The cheapest flight overall is $211 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $280.

  • 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.

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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
O'Hare Intl to Punta Cana flights
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Nassau flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to Saint Thomas Island flights
Midway to Montego Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Saint Thomas Island flights
O'Hare Intl to Providenciales flights
Midway to Nassau flights
Midway to Oranjestad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Christiansted flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
O'Hare Intl to Castries flights
Midway to Simpson Bay flights
Midway to Santo Domingo flights
St. Louis to Montego Bay flights
O'Hare Intl to St. John's flights
St. Louis to Nassau flights
Midway to George Town flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Puerto Plata flights
St. Louis to Oranjestad flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Castries flights
O'Hare Intl to Kingston flights
St. Louis to George Town flights
O'Hare Intl to Basseterre flights
St. Louis to Providenciales flights
O'Hare Intl to Road Town flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Freeport flights
Midway to Castries flights
St. Louis to Christiansted flights
O'Hare Intl to St. George's flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Port of Spain flights
St. Louis to Simpson Bay flights
O'Hare Intl to Gregory Town 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$205Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$266Average$440FlexibilityNo cancel feeOn-time65%
DeltaCheapest$368Average$650FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$382Average$584FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$393Average$707FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$579Average$724FlexibilityNo cancel feeOn-time63%
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