$187+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Jamaica to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Chicago
Keep the following information in mind while searching for Jamaica to Chicago flight deals. Data was last updated junio 12, 2025.
Round-trip from | $303 (Cheapflightsfares) |
|---|---|
One-way from | $187 (SmartFares) |
Popular in | January |
Cheapest in | September |
Average price | $597 |
Good round-trip deal | $463 or less |
Good one-way deal | $262 or less |
Find flight deals from Jamaica to Chicago
Cheapest flights from Jamaica to ChicagoExplore 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 junio 12, 2025.
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 junio 12, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
This United Airlines deal was found by Cheapflights users on 6/11. 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.
This Booking.com deal was found by Cheapflights users on 6/12. 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.
This SmartFares deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Mytrip deal was found by Cheapflights users on 6/10. 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.
This Mytrip deal was found by Cheapflights users on 6/10. 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.
This Orbitz deal was found by Cheapflights users on 6/9. 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.
This Southwest deal was found by Cheapflights users on 6/11. 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.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
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 junio 12, 2025.
Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
mié. 7/23
12:10 pm-11:13 pm
1 stop11h 03m
Chicago O'Hare Intl
sáb. 8/2
5:38 pm-9:53 am
1 stop16h 15m
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
vie. 6/27
2:23 pm-7:00 pm
Nonstop4h 37m
Chicago O'Hare Intl
lun. 6/30
8:44 am-12:42 pm
Nonstop3h 58m
KingstonChicago
KIN - ORD
KINORD
Kingston Norman Manley
vie. 7/11
1:37 pm-11:53 pm
1 stop10h 16m
Chicago O'Hare Intl
lun. 7/14
5:05 am-12:42 pm
1 stop7h 37m
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
dom. 7/27
1:51 pm-6:20 pm
Nonstop4h 29m
Chicago O'Hare Intl
dom. 8/3
8:42 am-12:49 pm
Nonstop4h 07m
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
vie. 8/1
3:53 pm-10:25 am
1 stop18h 32m
Chicago O'Hare Intl
sáb. 8/2
5:07 pm-7:55 am
1 stop14h 48m
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
dom. 6/15
9:18 am-11:18 pm
1 stop14h 00m
Chicago Midway
sáb. 6/21
6:20 am-2:43 pm
1 stop8h 23m
KingstonChicago
KIN - ORD
KINORD
Kingston Norman Manley
vie. 7/25
6:25 pm-9:09 am
1 stop14h 44m
Chicago O'Hare Intl
vie. 8/1
5:40 pm-7:47 am
1 stop14h 07m
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
jue. 7/3
3:05 pm-8:23 pm
2 stops29h 18m
Chicago O'Hare Intl
sáb. 7/12
5:05 am-11:05 am
1 stop6h 00m
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
mié. 6/18
2:55 pm-11:45 pm
1 stop8h 50m
Chicago Midway
lun. 6/23
7:45 am-1:20 pm
1 stop5h 35m
KingstonChicago
KIN - ORD
KINORD
Kingston Norman Manley
mié. 7/9
6:00 am-7:35 pm
1 stop13h 35m
Chicago O'Hare Intl
vie. 8/22
6:00 am-7:55 pm
1 stop13h 55m
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.
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 junio 12, 2025.
Unlike in the morning, when flights are generally more expensive, you can save up to 14% on flights from Jamaica to Chicago by exploring options for tickets at noon.
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 junio 12, 2025.
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 (2 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 junio 12, 2025.
See what other customers who have flown with Southwest, Delta and Copa 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.
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
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.
Traveling to a place near Jamaica?
Book flights to Jamaica if you plan to visit one of these locationsBrowse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Jamaica to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$251 | Average$358 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$255 | Average$480 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$322 | Average$410 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$357 | Average$543 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$509 | Average$608 | FlexibilityNo cancel fee | On-time63% |