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$161+ Cheap flights from Jamaica to Illinois

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 — ORD
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
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Cheap flight deals from Jamaica to Illinois

Keep the following information in mind while searching for Jamaica to Illinois flight deals. Data was last updated abril 29, 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 Illinois
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One-way flight from Jamaica to Illinois
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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 Illinois.
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Price to beat on a one-way flight from Jamaica to Illinois.
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Find flight deals from Jamaica to Illinois

Cheapest flights from Jamaica to Illinois
Explore the most affordable flight options available from Jamaica to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 29, 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.
mar. 6/2412:07 pmMBJ - ORD
1 stop11h 38mSpirit Airlines
mar. 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.
mié. 6/41:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
dom. 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.
mié. 6/49:00 amKIN - ORD
2 stops11h 21mDelta
lun. 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.
mié. 6/42:57 pmKIN - ORD
1 stop9h 37mCopa Airlines
mar. 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.
mié. 6/46:30 amKIN - ORD
2 stops11h 21mAmerican Airlines
mié. 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.
jue. 5/152:25 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
dom. 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.
mar. 6/39:08 amMBJ - MDW
1 stop13h 36mFrontier
mar. 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.
dom. 5/251:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
dom. 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.
sáb. 5/310:11 amMBJ - ORD
1 stop12h 11mJetBlue
jue. 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.
vie. 5/212:11 pmMBJ - ORD
1 stop6h 49mDelta
mié. 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.
sáb. 6/213:53 pmMBJ - ORD
1 stop8h 21mFrontier
dom. 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.
sáb. 5/3111:31 amMBJ - MDW
1 stop9h 42mDelta
dom. 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 Illinois 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 abril 29, 2025.
Use the filters below to find and compare flights from Jamaica to Illinois that are best for you.

Fly from

Jamaica

Fly to

Illinois

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 6/24

12:07 pm-11:45 pm

1 stop11h 38m

Chicago O'Hare Intl

mar. 7/15

6:34 pm-9:14 am

1 stop14h 40m

$296

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mié. 6/4

1:34 pm-11:04 pm

1 stop9h 30m

Chicago O'Hare Intl

dom. 6/29

5:05 am-12:28 pm

1 stop7h 23m

$331

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mié. 6/4

9:00 am-8:21 pm

2 stops11h 21m

Chicago O'Hare Intl

lun. 6/30

7:05 am-8:00 pm

2 stops12h 55m

$382

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mié. 6/4

2:57 pm-12:34 am

1 stop9h 37m

Chicago O'Hare Intl

mar. 7/1

1:07 am-1:53 pm

1 stop12h 46m

$383

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mié. 6/4

6:30 am-5:51 pm

2 stops11h 21m

Chicago O'Hare Intl

mié. 7/2

8:05 am-7:55 pm

2 stops11h 50m

$396

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jue. 5/15

2:25 pm-7:00 pm

Nonstop4h 35m

Chicago O'Hare Intl

dom. 5/18

5:00 am-11:30 am

1 stop6h 30m

$402

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mar. 6/3

9:08 am-10:44 pm

1 stop13h 36m

Chicago Midway

mar. 6/10

5:36 pm-12:37 pm

1 stop19h 01m

$412

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

dom. 5/25

1:51 pm-6:20 pm

Nonstop4h 29m

Chicago O'Hare Intl

dom. 8/31

6:00 am-1:10 pm

1 stop7h 10m

$431

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sáb. 6/21

3:53 pm-12:14 am

1 stop8h 21m

Chicago O'Hare Intl

dom. 7/13

5:01 am-7:55 am

1 stop26h 54m

$462

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 5/31

11:31 am-9:13 pm

1 stop9h 42m

Chicago Midway

dom. 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 Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

Currently, August is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $245). Flying from Jamaica to Illinois 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 IL?

Find hourly flight availability from Jamaica to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 29, 2025.

When flying from Jamaica to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Jamaica to Illinois

Explore weekly flight availability from Jamaica to Illinois. 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 abril 29, 2025.

The most flights from JM0 to USIL 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 Illinois by month

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

In terms of precipitation, rainfall in Illinois 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 Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

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

If weather is an important factor for your trip to Illinois, 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 Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated abril 29, 2025.
To help decide which airline to fly from Jamaica to Illinois, see what other customers have to say about Southwest, Delta and Copa Airlines. 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
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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 Illinois. 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 Illinois 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 Illinois for a low price.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $245). Flying from Jamaica to Illinois 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

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Alternative routes for Jamaica to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Jamaica to Illinois

Discover the top 5 airlines that operate flights from Jamaica to Illinois. 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 abril 29, 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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