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$161+ Cheap flights from Jamaica to Chicago (CHI)

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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Jamaica to Chicago

Keep the following information in mind while searching for Jamaica to Chicago flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$263
(Cheapflightsfares)

One-way from

$161
(Cheapflightsfares)

Popular in

January

Cheapest in

April

Average price

$480

Good round-trip deal

$400 or less

Good one-way deal

$322 or less
Provider with most accurate pricing for Montego Bay Sangster Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Chicago (CHI) flights.
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From Jamaica to Chicago (CHI)
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One-way flight from Jamaica to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Jamaica to Chicago (CHI).
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Price to beat on a one-way flight from Jamaica to Chicago (CHI).
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Find flight deals from Jamaica to Chicago

Cheapest flights from Jamaica to Chicago
Explore the most affordable flight options available from Jamaica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Wed 3/1912:07 pmMBJ - ORD
1 stop6h 43mSpirit Airlines
Wed 3/267:21 pmORD - MBJ
1 stop15h 41mSpirit Airlines
Deal found 2/19$263
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Wed 2/261:26 pmKIN - ORD
1 stop9h 37mSpirit Airlines
Wed 3/55:10 amORD - KIN
1 stop7h 18mSpirit Airlines
Deal found 2/19$346
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 3/125:00 amKIN - ORD
2 stops9h 24mAmerican Airlines
Sun 3/168:05 amORD - KIN
2 stops11h 30mAmerican Airlines
Deal found 2/18$404
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/191:48 pmMBJ - ORD
Nonstop4h 22mUnited Airlines
Wed 3/266:00 amORD - MBJ
1 stop7h 37mUnited Airlines
Deal found 2/19$404
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/197:00 amMBJ - MDW
2 stops11h 02mDelta
Wed 3/266:00 amMDW - MBJ
1 stop9h 23mDelta
Deal found 2/19$414
This American Airlines deal was found by Cheapflights users on 2/19. 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 8/122:15 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Sun 8/318:05 amORD - MBJ
Nonstop4h 00mAmerican Airlines
Deal found 2/19$440
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Sat 4/512:07 pmMBJ - ORD
3 stops45h 52mMultiple Airlines
Sat 4/127:49 pmORD - MBJ
1 stop16h 56mMultiple Airlines
Deal found 2/18$458
This Mytrip deal was found by Cheapflights users on 2/18. 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 3/121:36 pmKIN - ORD
2 stops18h 08mMultiple Airlines
Sun 3/165:55 amORD - KIN
3 stops38h 40mMultiple Airlines
Deal found 2/18$512
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/193:00 pmMBJ - MDW
1 stop8h 00mSouthwest
Wed 3/266:30 amMDW - MBJ
1 stop7h 30mSouthwest
Deal found 2/19$544
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 8/121:15 pmMBJ - ORD
1 stop8h 06mDelta
Sun 8/317:00 amORD - MBJ
2 stops8h 36mDelta
Deal found 2/18$549
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/189:09 amKIN - ORD
1 stop14h 16mJetBlue
Tue 7/2211:35 amORD - KIN
1 stop12h 18mJetBlue
Deal found 2/19$560
This Air Canada deal was found by Cheapflights users on 2/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/28:20 pmMBJ - ORD
2 stops13h 34mAir Canada
Sat 8/3010:00 amORD - MBJ
1 stop9h 25mAir Canada
Deal found 2/19$656

Find flights from Jamaica to Chicago within your budget

Customize your flight search to find flights from Jamaica to Chicago 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 February 20, 2025.

Fly from

Jamaica

Fly to

Chicago

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 3/19

12:07 pm-6:50 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 3/26

7:21 pm-11:02 am

1 stop15h 41m

$263

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 4/5

1:36 pm-8:44 am

2 stops19h 08m

Chicago O'Hare Intl

Sat 4/12

7:49 pm-12:31 pm

1 stop16h 42m

$360

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 3/12

5:00 am-2:24 pm

2 stops9h 24m

Chicago O'Hare Intl

Sun 3/16

8:05 am-7:35 pm

2 stops11h 30m

$404

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 3/19

1:48 pm-6:10 pm

Nonstop4h 22m

Chicago O'Hare Intl

Wed 3/26

6:00 am-1:37 pm

1 stop7h 37m

$404

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 3/19

7:00 am-6:02 pm

2 stops11h 02m

Chicago Midway

Wed 3/26

6:00 am-3:23 pm

1 stop9h 23m

$414

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 8/12

2:15 pm-6:50 pm

Nonstop4h 35m

Chicago O'Hare Intl

Sun 8/31

8:05 am-12:05 pm

Nonstop4h 00m

$440

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 4/5

12:07 pm-9:59 am

3 stops45h 52m

Chicago O'Hare Intl

Sat 4/12

7:49 pm-12:45 pm

1 stop16h 56m

$458

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 3/12

1:36 pm-7:44 am

2 stops18h 08m

Chicago O'Hare Intl

Sun 3/16

5:55 am-8:35 pm

3 stops38h 40m

$512

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 3/19

3:00 pm-11:00 pm

1 stop8h 00m

Chicago Midway

Wed 3/26

6:30 am-2:00 pm

1 stop7h 30m

$544

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 8/12

1:15 pm-9:21 pm

1 stop8h 06m

Chicago O'Hare Intl

Sun 8/31

7:00 am-3:36 pm

2 stops8h 36m

$549

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 29 results
1
2
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Best time to book a flight from Jamaica to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Jamaica 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 Jamaica to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $245). Flying from Jamaica to Chicago in March is currently the most expensive (average of $321). 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 JM to CHI?

Find hourly flight availability from Jamaica to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 2% on flights from Jamaica to Chicago by exploring options for tickets in the morning.

Weekly flight availability from Jamaica to Chicago

Explore weekly flight availability from Jamaica to Chicago. 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 February 20, 2025.

The most flights from JM0 to CHI are scheduled on a Monday (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 Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 20, 2025.
See what other customers who have flown with Southwest, Delta and JetBlue from Jamaica to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Jamaica to Chicago. 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 Jamaica to Chicago one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $161. However, be on the lookout for offers from Frontier and United Airlines, as they are both options that can get you from Jamaica to Chicago for a low price.

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

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

  • What are the most reliable airlines from Jamaica to Chicago?

    The top 3 most reliable airlines when flying from Jamaica to Chicago are American Airlines (71%), United Airlines (63%) and British Airways (56%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $435, our data indicates the cheapest price to be $256. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $263.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jamaica to Chicago 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 Jamaica to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $245). Flying from Jamaica to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Jamaica?

Book flights to Jamaica if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Jamaica to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
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Saint Thomas Island to St. Louis flights
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Saint Thomas Island to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Simpson Bay to Midway flights
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Roseau to O'Hare Intl flights
Port Au Prince to Midway flights
St. John's to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Vieques to O'Hare Intl flights
Oranjestad to St. Louis flights
St. George's to St. Louis flights
Culebra to O'Hare Intl flights
Aguadilla to Midway flights

Top 4 airlines flying from Jamaica to Chicago

Discover the top 4 airlines that operate flights from Jamaica to Chicago. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$355FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$436FlexibilityNo cancel feeOn-time69%
DeltaCheapest$322Average$415FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$357Average$537FlexibilityNo cancel feeOn-time71%
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