Jamaica

$118+ Cheap flights from Chicago (CHI) to Jamaica

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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Jun 2 — Jun 91
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Jamaica 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 Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/129:15 am
ORD
-
MBJ
Nonstop4h 16m
American Airlines
Thu 7/162:31 pm
MBJ
-
ORD
Nonstop4h 51m
American Airlines
Deal found 4/29$318
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.
Tue 11/37:10 am
ORD
-
MBJ
1 stop6h 40m
American Airlines
Tue 11/102:19 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 4/28$322
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.
Sun 12/138:10 am
ORD
-
MBJ
Nonstop4h 10m
American Airlines
Sun 12/204:27 pm
MBJ
-
ORD
Nonstop4h 37m
American Airlines
Deal found 4/28$323
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.
Sat 11/76:35 pm
ORD
-
MBJ
1 stop17h 19m
American Airlines
Sun 11/153:14 pm
MBJ
-
ORD
Nonstop4h 41m
American Airlines
Deal found 4/28$327
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Tue 5/121:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/28$328
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Fri 5/1510:17 am
MBJ
-
ORD
1 stop13h 37m
American Airlines
Deal found 4/29$328
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:30 am
ORD
-
MBJ
1 stop8h 00m
United Airlines
Thu 5/72:40 pm
MBJ
-
ORD
1 stop10h 05m
United Airlines
Deal found 4/29$332
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:05 am
ORD
-
MBJ
Nonstop4h 08m
American Airlines
Sat 5/210:13 am
MBJ
-
ORD
1 stop7h 45m
American Airlines
Deal found 4/29$333
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Tue 6/21:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/29$338
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.
Sat 9/196:35 pm
ORD
-
MBJ
1 stop14h 35m
American Airlines
Tue 9/293:15 pm
MBJ
-
ORD
1 stop17h 30m
American Airlines
Deal found 4/28$341
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Sun 5/171:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 4/29$348
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
MDW
-
MBJ
1 stop6h 11m
Frontier
Thu 5/211:16 pm
MBJ
-
MDW
1 stop8h 46m
Frontier
Deal found 5/3$358

Find flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated May 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$318
(American Airlines)

One-way from

$118
(Priceline)

Popular in

June

Cheapest in

January

Average price

$545

Good round-trip deal

$418 or less

Good one-way deal

$138 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
From Chicago (CHI) to Jamaica
One-way flight from Chicago (CHI) to Jamaica
Highest demand for flights based on searches. 4% potential increase in price ($27 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in May 2026
Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
Price to beat on a one-way flight from Chicago (CHI) to Jamaica.

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica 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 May 3, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 7/24

6:00 am-3:10 pm

1 stop9h 10m

Montego Bay Sangster Intl

Tue 7/28

4:12 pm-11:26 pm

1 stop7h 14m

$332

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 6/2

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Tue 6/9

4:12 pm-11:26 pm

1 stop7h 14m

$351

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 7/24

8:40 am-3:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Wed 7/29

4:12 pm-11:26 pm

1 stop7h 14m

$352

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 6/20

8:40 am-3:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Wed 6/24

4:12 pm-11:26 pm

1 stop7h 14m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 5/31

6:30 am-3:10 pm

1 stop8h 40m

Montego Bay Sangster Intl

Sun 6/7

4:12 pm-11:26 pm

1 stop7h 14m

$373

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 5/15

6:00 am-3:10 pm

1 stop9h 10m

Montego Bay Sangster Intl

Mon 5/18

4:12 pm-11:44 pm

1 stop7h 32m

$406

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 5/30

5:30 am-3:26 pm

1 stop9h 56m

Montego Bay Sangster Intl

Sat 6/6

4:12 pm-11:26 pm

1 stop7h 14m

$426

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 10/28

6:00 am-1:29 pm

1 stop7h 29m

Montego Bay Sangster Intl

Sun 11/1

2:48 pm-6:16 pm

Nonstop4h 28m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 7/22

6:00 am-2:55 pm

1 stop8h 55m

Montego Bay Sangster Intl

Wed 7/29

1:50 pm-5:50 pm

Nonstop4h 00m

$447

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 7/24

7:00 am-2:55 pm

1 stop7h 55m

Montego Bay Sangster Intl

Wed 7/29

1:50 pm-5:50 pm

Nonstop4h 00m

$450

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago 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 Chicago to Jamaica

How far ahead should I book a flight from Chicago to Jamaica?

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Jamaica. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, December is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $84). Flying from Chicago to Jamaica in May is currently the most expensive (average of $277). 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 CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 3, 2026.

When flying from Chicago to Jamaica, 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 Chicago to Jamaica

Explore weekly flight availability from Chicago to Jamaica. 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 May 3, 2026.

The most flights from CHI to JM0 are scheduled on a Saturday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated May 3, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Chicago to Jamaica?

    A quick flight from Chicago to Jamaica can take about 4h 16m. American Airlines provides one of the quickest options available for as low as $318. There are 1724 mi between Chicago and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Jamaica one-way?

    One-way options have recently been found by users for as low as $94 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $138 and United Airlines from $138 one-way.

  • What are the most popular routes from Chicago to Jamaica?

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $651 for a flight from Chicago to Jamaica. The cheapest flight overall is $138 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $332.

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

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

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

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

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

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

    Currently, December is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $84). Flying from Chicago to Jamaica in May is currently the most expensive (average of $277). 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

Browse 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.

Top 6 airlines flying from Chicago to Jamaica

Discover the top 6 airlines that operate flights from Chicago to Jamaica. 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 May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$457FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$675FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$537FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$302Average$526FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$323Average$651FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$468Average$653FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.