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$131+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

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 November 20, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/38:27 pmORD - KIN
1 stop14h 40mSpirit Airlines
Sat 12/710:14 amKIN - ORD
1 stop6h 52mSpirit Airlines
Deal found 11/19$346
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Sat 12/76:45 pmORD - KIN
1 stop17h 05mAmerican Airlines
Tue 12/106:35 amKIN - ORD
2 stops10h 34mAmerican Airlines
Deal found 11/19$363
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/167:45 pmORD - MBJ
2 stops40h 45mSpirit Airlines
Fri 12/202:45 pmMBJ - ORD
1 stop8h 08mSpirit Airlines
Deal found 11/19$448
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Tue 12/107:00 amORD - MBJ
1 stop6h 25mAmerican Airlines
Thu 12/123:23 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Deal found 11/19$458
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Sun 12/15:00 amORD - MBJ
1 stop7h 33mMultiple Airlines
Sat 12/72:19 pmMBJ - ORD
2 stops17h 24mMultiple Airlines
Deal found 11/19$462
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/96:00 amMDW - MBJ
1 stop7h 04mDelta
Fri 12/133:29 pmMBJ - MDW
1 stop7h 37mDelta
Deal found 11/19$468
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/18:41 amORD - MBJ
Nonstop4h 05mUnited Airlines
Tue 12/103:36 pmMBJ - ORD
1 stop8h 24mUnited Airlines
Deal found 11/19$488
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Tue 12/246:49 pmMDW - MBJ
1 stop17h 56mMultiple Airlines
Tue 12/312:38 pmMBJ - MDW
2 stops23h 46mMultiple Airlines
Deal found 11/19$494
This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:15 amMDW - MBJ
1 stop24h 39mFrontier
Tue 12/102:17 pmMBJ - MDW
1 stop22h 25mFrontier
Deal found 11/19$511
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/216:00 amORD - MBJ
1 stop9h 33mDelta
Sun 11/242:06 pmMBJ - ORD
1 stop10h 53mDelta
Deal found 11/19$518
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Sat 12/287:10 amORD - MBJ
1 stop28h 09mFrontier
Mon 12/3010:14 amMBJ - ORD
1 stop12h 58mFrontier
Deal found 11/19$543
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2510:00 amORD - KIN
3 stops22h 09mMultiple Airlines
Tue 12/311:12 pmKIN - ORD
2 stops19h 35mMultiple Airlines
Deal found 11/19$601

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 12/3

8:27 pm-12:07 pm

1 stop14h 40m

Kingston Norman Manley

Sat 12/7

10:14 am-4:06 pm

1 stop6h 52m

$346

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 12/7

6:45 pm-12:50 pm

1 stop17h 05m

Kingston Norman Manley

Tue 12/10

6:35 am-4:09 pm

2 stops10h 34m

$363

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 1/5

12:58 pm-1:45 pm

1 stop23h 47m

Montego Bay Sangster Intl

Sat 1/11

2:49 pm-9:55 am

1 stop20h 06m

$445

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/5

7:00 am-1:45 pm

3 stops29h 45m

Montego Bay Sangster Intl

Fri 1/10

2:42 pm-11:12 am

2 stops21h 30m

$445

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/9

4:08 pm-1:09 pm

2 stops44h 01m

Montego Bay Sangster Intl

Thu 1/16

11:44 am-6:01 pm

2 stops31h 17m

$448

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/13

6:00 am-2:37 pm

1 stop7h 37m

Montego Bay Sangster Intl

Thu 1/16

2:48 pm-6:10 pm

Nonstop4h 22m

$449

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/10

7:00 am-2:25 pm

1 stop6h 25m

Montego Bay Sangster Intl

Thu 12/12

3:23 pm-6:58 pm

Nonstop4h 35m

$458

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 12/1

5:00 am-1:33 pm

1 stop7h 33m

Montego Bay Sangster Intl

Sat 12/7

2:19 pm-6:43 am

2 stops17h 24m

$462

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 12/9

6:00 am-2:04 pm

1 stop7h 04m

Montego Bay Sangster Intl

Fri 12/13

3:29 pm-10:06 pm

1 stop7h 37m

$468

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/18

5:45 am-3:24 pm

1 stop8h 39m

Montego Bay Sangster Intl

Fri 2/28

8:00 am-1:45 pm

1 stop6h 45m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 $401). 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 November 20, 2024.

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 November 20, 2024.

The most flights from CHI to JM0 are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, 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 November 20, 2024.
See what other customers who have flown with Frontier, Southwest 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
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

KLM
7.8
Good
1,350 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,785 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $131 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $133 and United Airlines from $202 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 $700 for a flight from Chicago to Jamaica. The cheapest flight overall is $221 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $305.

  • 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 $401). 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
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
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
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O'Hare Intl to Castries flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Oranjestad flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Willemstad flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Puerto Plata flights
St. Louis to Saint Thomas Island flights
Midway to Providenciales flights
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St. Louis to Montego Bay flights
O'Hare Intl to Kralendijk flights
Midway to George Town flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
O'Hare Intl to Basseterre flights
St. Louis to Christiansted flights
Midway to Santo Domingo flights
St. Louis to Oranjestad flights
St. Louis to George Town flights
O'Hare Intl to Santiago de los Caballeros flights
Moline to Montego Bay flights
O'Hare Intl to Gregory Town flights
St. Louis to Providenciales flights
St. Louis to Willemstad flights
St. Louis to Nassau flights
O'Hare Intl to St. George's flights
St. Louis to Simpson Bay flights
St. Louis to Castries flights
O'Hare Intl to Georgetown flights
Midway to Castries flights
Peoria to Punta Cana flights
O'Hare Intl to Freeport flights
O'Hare Intl to Road 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$300FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$267Average$413FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$368Average$818FlexibilityNo cancel feeOn-time71%
DeltaCheapest$368Average$600FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$393Average$599FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$598Average$723FlexibilityNo cancel feeOn-time63%
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