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$165+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — CHI
Nov 5 — Nov 121
1 adult
Tue 11/5
Tue 11/12
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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 October 31, 2024.

This FlightHub deal was found by Cheapflights users on 10/30. 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.
Wed 12/42:38 pmMBJ - ORD
1 stop7h 29mSpirit Airlines
Sun 12/85:00 amORD - MBJ
1 stop7h 33mSpirit Airlines
Deal found 10/30$313
This FlightHub deal was found by Cheapflights users on 10/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1010:14 amKIN - ORD
1 stop6h 52mSpirit Airlines
Sat 12/145:00 amORD - KIN
1 stop6h 07mSpirit Airlines
Deal found 10/31$326
This FlightHub deal was found by Cheapflights users on 10/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1711:38 amMBJ - MDW
1 stop26h 46mFrontier
Sun 1/52:40 pmMDW - MBJ
1 stop17h 14mFrontier
Deal found 10/31$419
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/42:48 pmMBJ - ORD
Nonstop4h 22mUnited Airlines
Sun 12/88:41 amORD - MBJ
Nonstop4h 05mUnited Airlines
Deal found 10/30$423
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/212:38 pmMBJ - ORD
1 stop6h 25mMultiple Airlines
Mon 12/166:07 pmORD - MBJ
2 stops18h 26mMultiple Airlines
Deal found 10/29$431
This American Airlines deal was found by Cheapflights users on 10/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/213:30 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Mon 1/69:05 amORD - MBJ
Nonstop4h 15mAmerican Airlines
Deal found 10/31$437
This Delta deal was found by Cheapflights users on 10/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/218:00 amMBJ - ORD
2 stops14h 17mDelta
Mon 1/67:00 amORD - MBJ
2 stops12h 49mDelta
Deal found 10/31$443
This American Airlines deal was found by Cheapflights users on 10/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/208:23 amKIN - ORD
1 stop11h 02mAmerican Airlines
Fri 1/179:45 amORD - KIN
2 stops8h 05mAmerican Airlines
Deal found 10/31$492
This JetBlue deal was found by Cheapflights users on 10/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/151:30 amKIN - ORD
1 stop8h 48mJetBlue
Sun 1/510:11 amORD - KIN
1 stop11h 55mJetBlue
Deal found 10/30$532
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/172:38 pmMBJ - MDW
2 stops28h 18mMultiple Airlines
Thu 11/216:05 amMDW - MBJ
1 stop9h 05mMultiple Airlines
Deal found 10/29$542
This Mytrip deal was found by Cheapflights users on 10/31. 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.
Tue 11/52:45 pmKIN - ORD
2 stops18h 17mMultiple Airlines
Thu 11/76:00 amORD - KIN
3 stops29h 09mMultiple Airlines
Deal found 10/31$596
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sun 11/171:45 pmMBJ - MDW
2 stops10h 25mSouthwest
Thu 11/217:55 pmMDW - MBJ
2 stops15h 50mSouthwest
Deal found 10/29$722

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/4

2:38 pm-9:07 pm

1 stop7h 29m

$165

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 12/10

2:17 pm-11:42 am

1 stop22h 25m

$183

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/18

2:45 pm-6:39 am

2 stops16h 54m

$200

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 12/16

5:50 pm-8:06 am

1 stop15h 16m

$222

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/20

2:48 pm-6:10 pm

Nonstop4h 22m

$251

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/19

4:14 pm-11:53 pm

1 stop8h 39m

$256

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 1/15

2:05 pm-12:09 am

2 stops11h 04m

$267

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/21

3:05 pm-6:30 pm

Nonstop4h 25m

$271

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 12/2

2:45 pm-2:45 pm

1 stop25h 00m

$306

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/5

10:04 am-11:51 pm

1 stop14h 47m

$195

Flights are sorted by cheapest first

Deals found on 10/30

Showing 1-10 of 31 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 October 31, 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.

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 October 31, 2024.
See what other customers who have flown with Spirit Airlines, United 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
5,116 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

Southwest
8.1
Very good
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

JetBlue
7.5
Good
3,514 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,240 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.3

Reviews

1 / 10

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

WestJet
7.3
Good
2,804 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.3

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.

  • Can I find flights from Jamaica to Chicago for under $400 on Cheapflights?

    Yes, there are multiple flights from Jamaica to Chicago for under $400. The cheapest flight booked recently is on Spirit Airlines for just $313, but on average you can expect to pay $559.

  • Are there nonstop flights from Jamaica to Chicago for under $500 on Cheapflights?

    Cheapflights has at least 2 direct flights from Jamaica to Chicago under $500. A good price for a nonstop flight from Jamaica to Chicago is less than $430.

  • Are there last-minute flights available from Jamaica to Chicago for under $500?

    There are currently 4+ open flights from Jamaica to Chicago within the next 7 days for less than $500.

  • What days are nonstop flights available from Jamaica to Chicago?

    Nonstop flights can be found on the following days: Saturday.

  • How many flights depart from Jamaica to Chicago on average per day?

    On average, you can expect to see 2 flights from Jamaica to Chicago a day.
    Afternoon (Noon - 6pm) - 100% of flight departures

  • How long is the flight from Jamaica to Chicago?

    Departing from Jamaica to Chicago will take you 4h 22m. There are 1734 mi between Jamaica and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $165. However, be on the lookout for offers from Frontier and JetBlue, 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 (81%), British Airways (75%) and United Airlines (33%).

  • What are the cheapest flights from Jamaica to Chicago?

    Looking for the cheapest flight from Jamaica to Chicago? While on average our users pay $443, our data indicates the cheapest price to be $220. The most popular route (Montego Bay Sangster Intl - Chicago O'Hare Intl), is priced around $313.

  • What does MBJ to ORD mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport flight would often be abbreviated as a MBJ to ORD flight. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Jamaica to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Jamaica to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Jamaica to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Jamaica to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Jamaica to Chicago that allow pets onboard?

    Many airlines flying from Jamaica to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Jamaica to Chicago?

    Yes, you can often find last-minute deals on Jamaica to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Jamaica to Chicago flight deals updated?

    The Jamaica to Chicago flight deals you see on this page were last updated on 10/31.

  • 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.

See more FAQs

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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
Punta Cana to Midway flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Nassau to O'Hare Intl flights
Kingston to O'Hare Intl flights
Nassau to Midway flights
Port of Spain to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Simpson Bay to Midway flights
Saint Thomas Island to St. Louis flights
Christiansted to O'Hare Intl flights
Nassau to St. Louis flights
George Town to O'Hare Intl flights
Oranjestad to St. Louis flights
Port of Spain to St. Louis flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
St. John's to O'Hare Intl flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
St. George's to St. Louis 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$241Average$351FlexibilityNo cancel feeOn-time65%
DeltaCheapest$312Average$554FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$336Average$435FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$357Average$524FlexibilityNo cancel feeOn-time71%
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