$149+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — ORD
Feb 28 — Mar 71
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Jamaica to Illinois
Cheapest flights from Jamaica to IllinoisExplore 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 January 29, 2026.
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 January 29, 2026.
This Orbitz deal was found by Cheapflights users on 1/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:00 pm
MBJ
- ORD
1 stop9h 13m
Spirit Airlines
Wed 3/45:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:00 pm
MBJ
- ORD
1 stop7h 46m
Spirit Airlines
Tue 4/148:41 pm
ORD
- MBJ
1 stop14h 21m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:14 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Tue 4/148:10 am
ORD
- MBJ
Nonstop4h 05m
American Airlines
Deal found 1/27![American Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Tue 4/148:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 1/27![United Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:20 pm
MBJ
- ORD
1 stop8h 33m
American Airlines
Mon 5/186:58 pm
ORD
- MBJ
1 stop16h 53m
American Airlines
Deal found 1/27![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/131:15 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Tue 4/218:10 am
ORD
- MBJ
Nonstop4h 05m
American Airlines
Deal found 1/27![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2411:15 am
MBJ
- ORD
1 stop12h 39m
Delta
Tue 4/147:00 am
ORD
- MBJ
2 stops8h 17m
Delta
Deal found 1/27![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:40 pm
MBJ
- MDW
1 stop7h 05m
Delta
Mon 5/186:00 am
MDW
- MBJ
1 stop7h 16m
Delta
Deal found 1/27![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Tue 4/218:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 1/27![United Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:00 pm
KIN
- ORD
1 stop9h 17m
Multiple Airlines
Mon 8/315:32 pm
ORD
- KIN
1 stop17h 33m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:40 pm
MBJ
- ORD
1 stop10h 59m
Multiple Airlines
Sat 3/146:01 pm
ORD
- MBJ
2 stops16h 57m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$373
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:00 pm
KIN
- ORD
1 stop7h 48m
Spirit Airlines
Wed 5/275:32 pm
ORD
- KIN
1 stop17h 33m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$389
Find flight deals from Jamaica to Illinois
Keep the following information in mind while searching for Jamaica to Illinois flight deals. Data was last updated January 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $230 (Orbitz) |
One-way from | $149 (Super.com) |
Popular in | June |
Cheapest in | November |
Average price | $449 |
Good round-trip deal | $365 or less |
Good one-way deal | $282 or less |
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 January 29, 2026.
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
Tue 3/24
1:48 pm-6:13 pm
Nonstop4h 25m
Chicago O'Hare Intl
Tue 4/14
8:45 am-3:10 pm
1 stop6h 25m
$325
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 5/14
3:20 pm-11:53 pm
1 stop8h 33m
Chicago O'Hare Intl
Mon 5/18
6:58 pm-11:51 am
1 stop16h 53m
$335
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Mon 4/13
1:15 pm-5:58 pm
Nonstop4h 43m
Chicago O'Hare Intl
Tue 4/21
5:00 am-11:24 am
1 stop6h 24m
$350
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 5/14
4:55 pm-7:26 am
2 stops14h 31m
Chicago O'Hare Intl
Mon 5/18
7:10 am-1:16 pm
1 stop6h 06m
$351
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Tue 3/24
11:15 am-11:54 pm
1 stop12h 39m
Chicago O'Hare Intl
Tue 4/14
7:00 am-3:17 pm
2 stops8h 17m
$351
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Thu 5/14
2:40 pm-9:45 pm
1 stop7h 05m
Chicago Midway
Mon 5/18
6:00 am-1:16 pm
1 stop7h 16m
$351
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Mon 4/13
4:12 pm-11:43 pm
1 stop7h 31m
Chicago O'Hare Intl
Tue 4/21
8:45 am-3:10 pm
1 stop6h 25m
$365
KingstonChicago
KIN - ORD
KINORD
Kingston Norman Manley
Tue 5/19
12:00 pm-9:17 pm
1 stop9h 17m
Chicago O'Hare Intl
Mon 8/31
5:32 pm-11:05 am
1 stop17h 33m
$372
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 2/28
12:40 pm-10:39 pm
1 stop10h 59m
Chicago O'Hare Intl
Sat 3/14
6:01 pm-10:58 am
2 stops16h 57m
$373
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 4/17
1:52 pm-6:15 pm
Nonstop4h 23m
Chicago O'Hare Intl
Fri 5/1
8:05 pm-1:30 pm
1 stop17h 25m
$380
Showing 1-10 of 42 results
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, October is the cheapest month in which you can book a flight from Jamaica to Illinois (average of $289). Flying from Jamaica to Illinois in March is currently the most expensive (average of $455). 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 January 29, 2026.
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.
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 January 29, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Jamaica to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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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.
Top 4 airlines flying from Jamaica to Illinois
Discover the top 4 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 January 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$256 | Average$371 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$348 | Average$495 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$349 | Average$480 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$392 | Average$536 | FlexibilityNo cancel fee | On-time63% |