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$175+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Jamaica to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Jamaica (JM0) to Chicago (CHI). 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 21, 2024.

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 November 21, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/101:12 pmKIN - ORD
1 stop8h 55mSpirit Airlines
Sat 12/145:11 pmORD - KIN
1 stop14h 58mSpirit Airlines
Deal found 11/20$321
This FlightHub deal was found by Cheapflights users on 11/20. 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 12/42:38 pmMBJ - ORD
2 stops29h 12mSpirit Airlines
Fri 12/61:13 pmORD - MBJ
1 stop23h 32mSpirit Airlines
Deal found 11/20$358
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/121:50 pmKIN - ORD
1 stop11h 06mAmerican Airlines
Fri 2/282:55 pmORD - KIN
1 stop6h 30mAmerican Airlines
Deal found 11/20$377
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/232:48 pmMBJ - ORD
Nonstop4h 22mUnited Airlines
Thu 1/29:29 pmORD - MBJ
1 stop15h 31mUnited Airlines
Deal found 11/20$449
This Delta deal was found by Cheapflights users on 11/20. 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.
Sat 11/235:58 pmMBJ - ORD
1 stop7h 01mDelta
Thu 1/27:00 amORD - MBJ
2 stops12h 51mDelta
Deal found 11/20$473
This JetBlue deal was found by Cheapflights users on 11/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/111:30 amKIN - ORD
1 stop8h 48mJetBlue
Fri 2/2811:44 amORD - KIN
1 stop13h 47mJetBlue
Deal found 11/20$495
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/233:15 pmMBJ - ORD
Nonstop4h 30mAmerican Airlines
Thu 1/29:05 amORD - MBJ
Nonstop4h 15mAmerican Airlines
Deal found 11/20$505
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/41:45 pmMBJ - MDW
2 stops9h 35mSouthwest
Fri 12/68:35 pmMDW - MBJ
2 stops16h 30mSouthwest
Deal found 11/20$549
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/81:12 pmKIN - ORD
3 stops22h 05mMultiple Airlines
Fri 12/1311:55 amORD - KIN
3 stops20h 14mMultiple Airlines
Deal found 11/20$567
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/42:06 pmMBJ - MDW
1 stop8h 40mDelta
Fri 12/66:00 amMDW - MBJ
1 stop9h 26mDelta
Deal found 11/21$656
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 11/305:40 pmMBJ - MDW
1 stop18h 30mFrontier
Sat 12/77:15 amMDW - MBJ
1 stop24h 39mFrontier
Deal found 11/19$704
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/236:50 pmMBJ - ORD
2 stops17h 04mMultiple Airlines
Thu 1/211:12 amORD - MBJ
3 stops25h 18mMultiple Airlines
Deal found 11/20$773

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 1/22

1:15 pm-8:13 pm

1 stop7h 58m

Chicago O'Hare Intl

Wed 1/29

5:10 am-12:10 pm

1 stop6h 00m

$303

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/4

2:38 pm-6:50 pm

2 stops29h 12m

Chicago O'Hare Intl

Fri 12/6

1:13 pm-1:45 pm

1 stop23h 32m

$358

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 12/12

1:50 pm-11:56 pm

1 stop11h 06m

Chicago O'Hare Intl

Fri 2/28

2:55 pm-10:25 pm

1 stop6h 30m

$377

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 12/11

1:30 am-9:18 am

1 stop8h 48m

Chicago O'Hare Intl

Fri 2/28

11:44 am-2:31 am

1 stop13h 47m

$495

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/4

2:48 pm-6:10 pm

Nonstop4h 22m

Chicago O'Hare Intl

Fri 12/6

9:32 pm-2:00 pm

1 stop15h 28m

$495

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 1/13

1:15 pm-8:13 pm

1 stop7h 58m

Chicago O'Hare Intl

Fri 1/17

5:47 pm-12:10 pm

2 stops17h 23m

$497

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/4

11:20 am-11:55 pm

1 stop13h 35m

Chicago O'Hare Intl

Fri 12/6

9:18 am-2:23 pm

Nonstop4h 05m

$522

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/4

1:45 pm-10:25 pm

1 stop9h 40m

Chicago Midway

Fri 12/6

8:35 pm-2:05 pm

2 stops16h 30m

$549

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/4

2:06 pm-9:46 pm

1 stop8h 40m

Chicago Midway

Fri 12/6

6:00 am-4:26 pm

1 stop9h 26m

$656

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 1/14

9:00 am-8:53 pm

2 stops12h 53m

Chicago O'Hare Intl

Sat 1/18

6:55 am-8:00 pm

2 stops12h 05m

$703

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 28 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.

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, September is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $232). Flying from Jamaica to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Jamaica to Chicago as you normally would.

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 November 21, 2024.

The most flights from JM0 to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, 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 November 21, 2024.
See what other customers who have flown with United Airlines, Spirit Airlines and American 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
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,759 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

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

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

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
5,015 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

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

JetBlue
7.5
Good
3,395 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

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 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 Frontier, with whom users have recently found tickets for as low as $175. However, be on the lookout for offers from Spirit Airlines 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, 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 (98%), British Airways (97%) and United Airlines (95%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $419, our data indicates the cheapest price to be $249. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $336.

  • 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, September is the cheapest month in which you can book a flight from Jamaica to Chicago (average of $232). Flying from Jamaica to Chicago in June is currently the most expensive (average of $308). 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.

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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
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
George Town to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to Midway flights
Saint Thomas Island to St. Louis flights
Willemstad to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Road Town to O'Hare Intl flights
Port of Spain to St. Louis flights
Nassau to St. Louis flights
St. John's to O'Hare Intl flights
St. George's to St. Louis flights
Aguadilla to Midway flights
Oranjestad to St. Louis flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$250Average$368FlexibilityNo cancel feeOn-time65%
DeltaCheapest$312Average$472FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$336Average$432FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$357Average$534FlexibilityNo cancel feeOn-time71%
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