Jamaica

$129+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Dec 27 — Jan 31
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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 December 22, 2024.

Round-trip from

$324
(Priceline)

One-way from

$129
(Cheapflightsfares)
From Chicago (CHI) to Jamaica
One-way flight from Chicago (CHI) to Jamaica

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 December 22, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:00 amORD - MBJ
1 stop7h 30mSpirit Airlines
Wed 1/221:16 pmMBJ - ORD
1 stop11h 16mSpirit Airlines
Deal found 12/21$470
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Tue 12/319:05 amORD - MBJ
Nonstop4h 15mAmerican Airlines
Wed 1/222:05 pmMBJ - ORD
1 stop8h 48mAmerican Airlines
Deal found 12/21$500
This Booking.com deal was found by Cheapflights users on 12/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:00 amORD - MBJ
1 stop7h 30mMultiple Airlines
Wed 1/110:29 amMBJ - ORD
1 stop12h 16mMultiple Airlines
Deal found 12/21$624
This United deal was found by Cheapflights users on 12/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:41 amORD - MBJ
Nonstop4h 05mUnited Airlines
Wed 1/222:48 pmMBJ - ORD
Nonstop4h 22mUnited Airlines
Deal found 12/21$663
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/2510:50 amMDW - MBJ
2 stops25h 40mMultiple Airlines
Fri 12/2710:14 amMBJ - MDW
1 stop14h 00mMultiple Airlines
Deal found 12/21$717
This FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:14 pmORD - KIN
2 stops14h 53mSpirit Airlines
Sun 12/2910:14 amKIN - ORD
2 stops22h 33mSpirit Airlines
Deal found 12/20$728
This Orbitz deal was found by Cheapflights users on 12/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/248:25 pmORD - MBJ
2 stops16h 20mAir Canada
Mon 12/302:45 pmMBJ - ORD
2 stops23h 26mAir Canada
Deal found 12/21$741
This Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/292:40 pmMDW - MBJ
1 stop17h 14mFrontier
Wed 1/110:29 amMBJ - MDW
1 stop11h 48mFrontier
Deal found 12/21$754
This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:45 amORD - MBJ
1 stop6h 18mDelta
Mon 12/308:00 amMBJ - ORD
1 stop9h 12mDelta
Deal found 12/20$801
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Mon 12/304:28 pmORD - MBJ
1 stop15h 41mFrontier
Sun 1/51:29 pmMBJ - ORD
1 stop8h 40mFrontier
Deal found 12/21$822
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Sun 12/225:35 pmORD - KIN
1 stop16h 00mAmerican Airlines
Sat 12/283:18 pmKIN - ORD
1 stop10h 08mAmerican Airlines
Deal found 12/21$849
This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2510:08 amMDW - KIN
1 stop9h 51mDelta
Sun 12/2910:00 amKIN - MDW
1 stop7h 17mDelta
Deal found 12/20$861

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 2/1

5:11 am-1:33 pm

1 stop7h 22m

Kingston Norman Manley

Tue 2/4

2:38 pm-8:13 pm

1 stop6h 35m

$324

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 2/1

5:11 am-1:33 pm

1 stop7h 22m

Kingston Norman Manley

Tue 2/4

2:38 pm-12:45 pm

2 stops23h 07m

$387

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 1/29

10:09 am-6:50 pm

1 stop7h 41m

Kingston Norman Manley

Thu 2/6

6:48 am-4:14 pm

2 stops10h 26m

$432

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 2/15

5:35 am-1:36 pm

2 stops31h 01m

Montego Bay Sangster Intl

Wed 2/19

2:41 pm-4:38 pm

2 stops26h 57m

$445

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/22

8:01 pm-10:34 am

1 stop13h 33m

Montego Bay Sangster Intl

Sun 1/26

11:48 am-9:32 pm

1 stop10h 44m

$446

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/17

8:12 pm-1:10 pm

1 stop15h 58m

Montego Bay Sangster Intl

Tue 1/21

1:16 pm-11:20 am

2 stops47h 04m

$446

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/20

8:41 am-1:46 pm

Nonstop4h 05m

Montego Bay Sangster Intl

Thu 1/23

2:48 pm-6:10 pm

Nonstop4h 22m

$465

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/4

6:00 am-12:47 pm

1 stop5h 47m

Montego Bay Sangster Intl

Tue 2/11

12:36 pm-10:20 pm

1 stop10h 44m

$479

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/25

11:20 am-8:37 pm

1 stop9h 17m

Montego Bay Sangster Intl

Wed 4/2

7:00 am-4:19 pm

1 stop9h 19m

$479

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/26

9:13 am-2:23 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Mon 2/3

3:23 pm-6:58 pm

Nonstop4h 35m

$490

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 36 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 December 22, 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 December 22, 2024.

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 December 22, 2024.
See what other customers who have flown with Spirit Airlines, American Airlines and United 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.
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

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.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

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.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

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.

7.4
Good
3,265 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

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.

7.4
Good
9,028 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

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.

7.2
Good
10,000 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

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 $129 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $132 and United Airlines from $212 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 $726 for a flight from Chicago to Jamaica. The cheapest flight overall is $167 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $291.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$267Average$417FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$368Average$778FlexibilityNo cancel feeOn-time71%
DeltaCheapest$368Average$589FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$393Average$596FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$579Average$723FlexibilityNo cancel feeOn-time63%
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