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$149+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$294
(FlightHub)

One-way from

$149
(FlightHub)

Popular in

January

Cheapest in

September

Average price

$508

Good round-trip deal

$410 or less

Good one-way deal

$209 or less
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. 9% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/1312:19 pmMBJ - ORD
1 stop6h 48mSpirit Airlines
mié. 10/155:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 7/29$294
This Delta deal was found by Cheapflights users on 7/29. 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.
jue. 10/22:35 pmMBJ - MDW
1 stop7h 01mDelta
lun. 10/66:00 amMDW - MBJ
1 stop9h 34mDelta
Deal found 7/29$339
This Mytrip deal was found by Cheapflights users on 7/31. 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.
jue. 8/1410:22 amMBJ - ORD
1 stop8h 45mMultiple Airlines
jue. 8/216:00 pmORD - MBJ
1 stop13h 55mMultiple Airlines
Deal found 7/31$348
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/212:50 pmMBJ - MDW
2 stops7h 50mSouthwest
lun. 10/65:00 amMDW - MBJ
1 stop8h 55mSouthwest
Deal found 7/29$348
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
sáb. 9/2012:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
sáb. 9/276:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Deal found 7/31$351
This Frontier deal was found by Cheapflights users on 7/31. 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.
dom. 9/142:12 pmMBJ - MDW
1 stop9h 08mFrontier
dom. 9/216:20 amMDW - MBJ
1 stop6h 21mFrontier
Deal found 7/31$352
This FlightHub deal was found by Cheapflights users on 7/30. 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.
jue. 8/79:10 amMBJ - ORD
1 stop15h 12mFrontier
mar. 8/125:38 pmORD - MBJ
1 stop14h 17mFrontier
Deal found 7/30$359
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/121:55 pmMBJ - ORD
2 stops9h 53mAmerican Airlines
vie. 9/196:52 pmORD - MBJ
1 stop15h 40mAmerican Airlines
Deal found 7/29$378
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/52:17 pmMBJ - ORD
1 stop9h 24mUnited Airlines
mar. 8/128:52 amORD - MBJ
1 stop6h 18mUnited Airlines
Deal found 7/29$401
This American Airlines deal was found by Cheapflights users on 7/30. 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.
sáb. 9/131:00 pmKIN - ORD
2 stops10h 48mAmerican Airlines
sáb. 9/208:37 amORD - KIN
2 stops11h 01mAmerican Airlines
Deal found 7/30$416
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/122:20 amKIN - ORD
1 stop14h 01mJetBlue
sáb. 9/208:34 amORD - KIN
1 stop16h 36mJetBlue
Deal found 7/30$489
This Kiwi.com deal was found by Cheapflights users on 7/30. 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. 8/79:10 amMBJ - MDW
1 stop14h 07mMultiple Airlines
lun. 8/116:20 amMDW - MBJ
2 stops28h 45mMultiple Airlines
Deal found 7/30$550

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 julio 31, 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

mié. 8/13

12:19 pm-7:07 pm

1 stop6h 48m

Chicago O'Hare Intl

mié. 10/15

5:05 am-11:05 am

1 stop6h 00m

$294

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jue. 10/2

2:35 pm-9:36 pm

1 stop7h 01m

Chicago Midway

lun. 10/6

6:00 am-3:34 pm

1 stop9h 34m

$339

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jue. 8/14

10:22 am-7:07 pm

1 stop8h 45m

Chicago O'Hare Intl

jue. 8/21

6:00 pm-7:55 am

1 stop13h 55m

$348

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jue. 10/2

12:50 pm-8:40 pm

2 stops7h 50m

Chicago Midway

lun. 10/6

5:00 am-1:55 pm

1 stop8h 55m

$348

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

sáb. 9/20

12:08 pm-10:48 pm

1 stop10h 40m

Chicago O'Hare Intl

sáb. 9/27

6:44 pm-11:02 am

1 stop16h 18m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

dom. 9/14

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

dom. 9/21

6:20 am-12:41 pm

1 stop6h 21m

$352

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

dom. 9/14

2:12 pm-12:10 am

1 stop9h 58m

Chicago O'Hare Intl

dom. 9/21

5:10 am-12:41 pm

1 stop7h 31m

$362

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

vie. 9/12

1:55 pm-11:48 pm

2 stops9h 53m

Chicago O'Hare Intl

vie. 9/19

6:52 pm-10:32 am

1 stop15h 40m

$378

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

sáb. 9/13

1:00 pm-11:48 pm

2 stops10h 48m

Chicago O'Hare Intl

sáb. 9/20

8:37 am-7:38 pm

2 stops11h 01m

$416

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

vie. 9/12

2:20 am-4:21 pm

1 stop14h 01m

Chicago O'Hare Intl

sáb. 9/20

8:34 am-1:10 am

1 stop16h 36m

$489

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 25 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 julio 31, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 3% on flights from Jamaica to Chicago by exploring options for tickets at noon.

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 julio 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Jamaica to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $149. However, be on the lookout for offers from United Airlines and Delta, 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 Qatar Airways (100%), United Airlines (88%) and American Airlines (85%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $388, our data indicates the cheapest price to be $167. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $301.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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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Santo Domingo to Midway flights
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Nassau to O'Hare Intl flights
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Nassau to Midway flights
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George Town to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
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Montego Bay to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
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Willemstad to O'Hare Intl flights
Simpson Bay to Midway flights
Bridgetown to O'Hare Intl flights
Oranjestad to St. Louis flights
St. John's to O'Hare Intl flights
Kingston to O'Hare Intl flights
Port of Spain to St. Louis flights
Roseau to O'Hare Intl flights
Nassau to St. Louis flights
St. George's to St. Louis flights
Saint Thomas Island to St. Louis flights
Vieques to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$360FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$255Average$480FlexibilityNo cancel feeOn-time69%
DeltaCheapest$322Average$411FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$392Average$550FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$392Average$529FlexibilityNo cancel feeOn-time71%

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