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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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$296
(SmartFares)

One-way from

$161
(Cheapflightsfares)

Popular in

January

Cheapest in

May

Average price

$406

Good round-trip deal

$479 or less

Good one-way deal

$287 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. 8% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This SmartFares deal was found by Cheapflights users on 4/27. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2412:07 pmMBJ - ORD
1 stop11h 38mSpirit Airlines
Tue 7/156:34 pmORD - MBJ
1 stop14h 40mSpirit Airlines
Deal found 4/27$296
This Booking.com deal was found by Cheapflights users on 4/28. 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.
Wed 6/41:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
Sun 6/295:05 amORD - KIN
1 stop7h 23mSpirit Airlines
Deal found 4/28$331
This Delta deal was found by Cheapflights users on 4/28. 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 6/49:00 amKIN - ORD
2 stops11h 21mDelta
Mon 6/307:05 amORD - KIN
2 stops12h 55mDelta
Deal found 4/28$382
This Copa Airlines deal was found by Cheapflights users on 4/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/42:57 pmKIN - ORD
1 stop9h 37mCopa Airlines
Tue 7/11:07 amORD - KIN
1 stop12h 46mCopa Airlines
Deal found 4/28$383
This American Airlines deal was found by Cheapflights users on 4/28. 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 6/46:30 amKIN - ORD
2 stops11h 21mAmerican Airlines
Wed 7/28:05 amORD - KIN
2 stops11h 50mAmerican Airlines
Deal found 4/28$396
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 5/152:25 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Sun 5/185:00 amORD - MBJ
1 stop6h 30mAmerican Airlines
Deal found 4/28$402
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/39:08 amMBJ - MDW
1 stop13h 36mFrontier
Tue 6/105:36 pmMDW - MBJ
1 stop19h 01mFrontier
Deal found 4/29$412
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/251:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Sun 8/316:00 amORD - MBJ
1 stop7h 10mUnited Airlines
Deal found 4/28$431
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/310:11 amMBJ - ORD
1 stop12h 11mJetBlue
Thu 7/316:00 amORD - MBJ
1 stop9h 06mJetBlue
Deal found 4/29$443
This Delta deal was found by Cheapflights users on 4/28. 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.
Fri 5/212:11 pmMBJ - ORD
1 stop6h 49mDelta
Wed 5/77:05 amORD - MBJ
1 stop5h 53mDelta
Deal found 4/28$455
This Booking.com deal was found by Cheapflights users on 4/27. 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.
Sat 6/213:53 pmMBJ - ORD
1 stop8h 21mFrontier
Sun 7/135:01 amORD - MBJ
1 stop26h 54mFrontier
Deal found 4/27$462
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/3111:31 amMBJ - MDW
1 stop9h 42mDelta
Sun 6/86:00 amMDW - MBJ
1 stop9h 25mDelta
Deal found 4/29$462

Cheapflights Fare Finder

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 April 30, 2025.
Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.

Fly from

Jamaica

Fly to

Chicago

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/24

12:07 pm-11:45 pm

1 stop11h 38m

Chicago O'Hare Intl

Tue 7/15

6:34 pm-9:14 am

1 stop14h 40m

$296

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/4

1:34 pm-11:04 pm

1 stop9h 30m

Chicago O'Hare Intl

Sun 6/29

5:05 am-12:28 pm

1 stop7h 23m

$331

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/4

9:00 am-8:21 pm

2 stops11h 21m

Chicago O'Hare Intl

Mon 6/30

7:05 am-8:00 pm

2 stops12h 55m

$382

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/4

2:57 pm-12:34 am

1 stop9h 37m

Chicago O'Hare Intl

Tue 7/1

1:07 am-1:53 pm

1 stop12h 46m

$383

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 6/4

6:30 am-5:51 pm

2 stops11h 21m

Chicago O'Hare Intl

Wed 7/2

8:05 am-7:55 pm

2 stops11h 50m

$396

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/15

2:25 pm-7:00 pm

Nonstop4h 35m

Chicago O'Hare Intl

Sun 5/18

5:00 am-11:30 am

1 stop6h 30m

$402

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 6/3

9:08 am-10:44 pm

1 stop13h 36m

Chicago Midway

Tue 6/10

5:36 pm-12:37 pm

1 stop19h 01m

$412

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 5/25

1:51 pm-6:20 pm

Nonstop4h 29m

Chicago O'Hare Intl

Sun 8/31

6:00 am-1:10 pm

1 stop7h 10m

$431

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 6/21

3:53 pm-12:14 am

1 stop8h 21m

Chicago O'Hare Intl

Sun 7/13

5:01 am-7:55 am

1 stop26h 54m

$462

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/31

11:31 am-9:13 pm

1 stop9h 42m

Chicago Midway

Sun 6/8

6:00 am-3:25 pm

1 stop9h 25m

$462

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 33 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Jamaica to Chicago

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 April 30, 2025.

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

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 April 30, 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 (2 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 April 30, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines 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
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,411 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 American Airlines and Frontier, 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, Kingston Norman Manley - Chicago O'Hare Intl and Montego Bay Sangster Intl - Chicago Midway.

  • 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 (74%), British Airways (74%) and United Airlines (70%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $408, our data indicates the cheapest price to be $241. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $296.

  • 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
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.
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Luis Munoz Marin Intl to Midway flights
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Nassau to Midway flights
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Willemstad to O'Hare Intl flights
St. George's to St. Louis flights
Nassau to St. Louis flights
Aguadilla to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
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Simpson Bay to Midway flights
Culebra to O'Hare Intl flights
St. John's to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Port of Spain to St. Louis flights
Aguadilla to Midway flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights

Top 5 airlines flying from Jamaica to Chicago

Discover the top 5 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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$358FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$491FlexibilityNo cancel feeOn-time69%
DeltaCheapest$322Average$411FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$357Average$547FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$451Average$657FlexibilityNo cancel feeOn-time63%

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