What airlines fly to Jamaica?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Jamaica from Chicago according to our data. American Airlines is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 6 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Jamaica?

Air Canada, United Airlines, and Delta are the most popular carriers operating from Chicago to Jamaica

When did momondo last update prices for flights from Chicago to Jamaica?

Prices for flights from Chicago to Jamaica refresh daily.

How many operators does momondo search for flights from Chicago to Jamaica?

As of October 2026, there are 6 operators available to choose from for flights from Chicago to Jamaica.

How old do you have to be to fly from Chicago to Jamaica?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Jamaica.

What documentation or ID do you need to fly to Jamaica?

The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$178 Cheap Flights from Chicago to Jamaica in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Jamaica

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:45 am - 5:20 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 35m1 stop Toronto Pearson Intl

2:22 pm - 9:42 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

8h 20m1 stop Atlanta Hartsfield-Jackson

$464Multiple Airlines

Wed, Dec 2 - Sun, Dec 6

6:05 am - 2:35 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 30m1 stop Miami

4:18 pm - 7:58 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 40mnonstop

$465American Airlines

Wed, Jan 20 - Wed, Jan 27

7:45 pm - 9:38 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

12h 53m1 stop Fort Lauderdale

3:45 pm - 11:42 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

8h 57m1 stop Fort Lauderdale

$465JetBlue

Mon, Jan 25 - Fri, Jan 29

7:45 pm - 9:38 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

12h 53m1 stop Fort Lauderdale

3:45 pm - 11:42 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

8h 57m1 stop Fort Lauderdale

$465JetBlue

Sun, Jan 24 - Fri, Jan 29

10:05 am - 3:18 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 13mnonstop

1:25 pm - 11:30 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

11h 05m1 stop Philadelphia

$465American Airlines

Sun, Jan 24 - Fri, Jan 29

5:26 pm - 12:56 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

18h 30m1 stop Atlanta Hartsfield-Jackson

6:20 pm - 8:00 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

14h 40m2 stops Toronto Pearson Intl Ottawa

$466Multiple Airlines

Tue, Nov 24 - Mon, Nov 30

5:00 am - 2:14 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

8h 14m1 stop Newark

3:20 pm - 12:01 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 41m1 stop Newark

$469United Airlines

Wed, Nov 18 - Wed, Nov 25

5:00 am - 2:14 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

8h 14m1 stop Newark

3:20 pm - 12:01 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 41m1 stop Newark

$469United Airlines

Wed, Nov 18 - Wed, Nov 25

8:10 am - 2:45 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

5h 35m1 stop Orlando

1:50 pm - 7:35 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

6h 45m1 stop Orlando

$469Southwest

Tue, Dec 1 - Fri, Dec 4

5:05 am - 2:45 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

8h 40m2 stops Baltimore/Washington Orlando

1:50 pm - 8:35 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

7h 45m1 stop Orlando

$473Southwest

Mon, Nov 9 - Thu, Nov 12

Cheap last minute flights

Enter your travel dates to find the best prices.

8:40 am - 12:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

$508United Airlines

Tue, Oct 27 - Mon, Nov 2

6:00 am - 4:12 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

10h 12m1 stop Dallas/Fort Worth

3:56 pm - 7:46 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 50mnonstop

$512American Airlines

Tue, Oct 27 - Mon, Nov 2

5:59 am - 1:14 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 15m1 stop Newark

2:01 pm - 6:27 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

$512United Airlines

Mon, Oct 26 - Thu, Oct 29

5:05 am - 11:18 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

6h 13m1 stop Miami

3:56 pm - 7:46 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 50mnonstop

$517American Airlines

Wed, Oct 28 - Mon, Nov 2

8:05 am - 3:27 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 22m1 stop Atlanta Hartsfield-Jackson

4:42 pm - 7:41 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

14h 59m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

$527Delta

Mon, Oct 26 - Thu, Oct 29

7:28 pm - 2:29 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

19h 01m1 stop Atlanta Hartsfield-Jackson

1:50 pm - 9:23 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

20h 33m1 stop Toronto Pearson Intl

$533Multiple Airlines

Wed, Oct 28 - Mon, Nov 2

7:28 pm - 2:29 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

19h 01m1 stop Atlanta Hartsfield-Jackson

6:20 pm - 8:00 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

14h 40m2 stops Toronto Pearson Intl Ottawa

$533Multiple Airlines

Wed, Oct 28 - Mon, Nov 2

6:42 pm - 2:29 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

19h 47m1 stop Atlanta Hartsfield-Jackson

4:43 pm - 11:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

8h 04m1 stop Atlanta Hartsfield-Jackson

$576Frontier

Wed, Oct 28 - Sun, Nov 1

6:42 pm - 2:29 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

19h 47m1 stop Atlanta Hartsfield-Jackson

4:43 pm - 11:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

8h 04m1 stop Atlanta Hartsfield-Jackson

$646Frontier

Wed, Oct 28 - Sun, Nov 1

7:00 am - 3:27 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

8h 27m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

4:42 pm - 7:41 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

14h 59m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

$806Delta

Mon, Oct 26 - Thu, Oct 29

Cheap direct flights

Enter your travel dates to find the best prices.

9:40 am - 2:53 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 13mnonstop

3:58 pm - 7:45 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 47mnonstop

$476American Airlines

Sun, Dec 6 - Wed, Dec 9

10:05 am - 3:18 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 13mnonstop

4:18 pm - 7:58 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 40mnonstop

$477American Airlines

Sun, Jan 24 - Fri, Jan 29

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

$481United Airlines

Mon, Nov 16 - Sat, Nov 21

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

$481United Airlines

Sun, Nov 8 - Wed, Nov 11

10:05 am - 3:18 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 13mnonstop

4:18 pm - 7:58 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 40mnonstop

$482American Airlines

Sun, Jan 24 - Mon, Feb 1

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

$482United Airlines

Mon, Jan 25 - Sat, Jan 30

7:55 am - 12:50 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

3h 55mnonstop

1:25 pm - 4:30 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

4h 05mnonstop

$557Southwest

Sat, Jan 23 - Sat, Jan 30

7:55 am - 12:50 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

3h 55mnonstop

1:25 pm - 4:30 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

4h 05mnonstop

$557Southwest

Sat, Jan 23 - Sat, Jan 30

8:40 am - 12:50 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 10mnonstop

1:52 pm - 6:15 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 23mnonstop

$1,795Virgin Australia

Sat, Apr 17 - Sat, Apr 24

10:21 am - 2:28 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 07mnonstop

3:00 pm - 7:46 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 46mnonstop

$2,745Multiple Airlines

Sat, Mar 27 - Sat, Apr 3

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American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets

American Airlines

Jan 24

ORD10:05 amChicago O'Hare Intl

4h 13m

MBJ3:18 pmMontego Bay Sangster Intl

Jan 29

MBJ1:25 pmMontego Bay Sangster Intl

11h 05m

1 stop

ORD11:30 pmChicago O'Hare Intl

$467

American Airlines

Dec 5

ORD6:47 pmChicago O'Hare Intl

16h 37m

1 stop

MBJ12:24 pmMontego Bay Sangster Intl

Dec 8

MBJ2:26 pmMontego Bay Sangster Intl

9h 34m

1 stop

ORD11:00 pmChicago O'Hare Intl

$471

American Airlines

Jan 24

ORD10:05 amChicago O'Hare Intl

4h 13m

MBJ3:18 pmMontego Bay Sangster Intl

Jan 29

MBJ4:18 pmMontego Bay Sangster Intl

4h 40m

ORD7:58 pmChicago O'Hare Intl

$477

Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets

Southwest

Dec 1

MDW8:10 amChicago Midway

5h 35m

1 stop

MBJ2:45 pmMontego Bay Sangster Intl

Dec 4

MBJ1:50 pmMontego Bay Sangster Intl

6h 45m

1 stop

MDW7:35 pmChicago Midway

$469

Southwest

Nov 9

MDW5:05 amChicago Midway

8h 40m

2 stops

MBJ2:45 pmMontego Bay Sangster Intl

Nov 12

MBJ1:50 pmMontego Bay Sangster Intl

7h 45m

1 stop

MDW8:35 pmChicago Midway

$473

Southwest

Dec 1

MDW6:00 amChicago Midway

7h 25m

1 stop

MBJ2:25 pmMontego Bay Sangster Intl

Dec 4

MBJ1:00 pmMontego Bay Sangster Intl

9h 30m

1 stop

MDW9:30 pmChicago Midway

$475

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Wed 12/2

8:45 am-5:20 pm

1 stop7h 35m

Montego Bay Sangster Intl

Sun 12/6

2:22 pm-9:42 pm

1 stop8h 20m

$464

Quickest round-trip

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Wed 1/20

6:05 am-2:35 pm

1 stop7h 30m

Montego Bay Sangster Intl

Wed 1/27

4:18 pm-7:58 pm

Nonstop4h 40m

$465

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Mon 1/25

7:45 pm-9:38 am

1 stop12h 53m

Montego Bay Sangster Intl

Fri 1/29

3:45 pm-11:42 pm

1 stop8h 57m

$465

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sun 1/24

7:45 pm-9:38 am

1 stop12h 53m

Montego Bay Sangster Intl

Fri 1/29

3:45 pm-11:42 pm

1 stop8h 57m

$465

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sun 1/24

10:05 am-3:18 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Fri 1/29

1:25 pm-11:30 pm

1 stop11h 05m

$465

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Tue 11/24

5:26 pm-12:56 pm

1 stop18h 30m

Montego Bay Sangster Intl

Mon 11/30

6:20 pm-8:00 am

2 stops14h 40m

$466

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Wed 11/18

5:00 am-2:14 pm

1 stop8h 14m

Montego Bay Sangster Intl

Wed 11/25

3:20 pm-12:01 am

1 stop9h 41m

$469

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Wed 11/18

5:00 am-2:14 pm

1 stop8h 14m

Montego Bay Sangster Intl

Wed 11/25

3:20 pm-12:01 am

1 stop9h 41m

$469

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Tue 12/1

8:10 am-2:45 pm

1 stop5h 35m

Montego Bay Sangster Intl

Fri 12/4

1:50 pm-7:35 pm

1 stop6h 45m

$469

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Mon 11/9

5:05 am-2:45 pm

2 stops8h 40m

Montego Bay Sangster Intl

Thu 11/12

1:50 pm-8:35 pm

1 stop7h 45m

$473

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Jamaica

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Jamaica?

The cheapest month to fly to Jamaica from Chicago is in April. Flight prices, which tend to average around $475, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of April, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $517.

What is the cheapest day to depart on your flight to Jamaica?

The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $485. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $627.

What is the cheapest Chicago to Jamaica flight route?

Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago - Jamaica flight prices

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

You are more likely to see cheaper flights to Jamaica from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $559 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Chicago for as low as $481 on momondo.

What cabin class options are available on Chicago to Jamaica flights?

There are 3 cabin classes available to choose from on Chicago to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Jamaica flights?

No. A direct flight is the cheapest option for a flight between Chicago to Jamaica.

Cheap Chicago to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Jamaica

Best Price Found	$178
Fastest flight time	3h 55m
Direct flights	Mon, Tue, Wed, Thu, Sat and Sun
Airports in Jamaica	11 airports

The best one-way flight to Jamaica from Chicago in the past 72 hours is $178. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $464.

The fastest flight from Chicago to Jamaica takes 3h 55m

Direct flights go from Chicago to Jamaica on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.

There are 11 airports in Jamaica. From Chicago there are direct flights to Montego Bay Sangster Intl (MBJ).

Search flight deals

Frequently asked questions about flying from Chicago to Jamaica

When did momondo last update prices for flights from Chicago to Jamaica?
Prices for flights from Chicago to Jamaica refresh daily.
How many operators does momondo search for flights from Chicago to Jamaica?
As of October 2026, there are 6 operators available to choose from for flights from Chicago to Jamaica.
How old do you have to be to fly from Chicago to Jamaica?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Jamaica.
What documentation or ID do you need to fly to Jamaica?
The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Jamaica?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Jamaica is Boeing 737-800 (84.23% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (7.06%), Boeing 737 (3.45%), and Boeing 737 MAX 8 (3.30%).

Best airlines flying from Chicago to Jamaica

Compare and see reviews for airlines that fly from Chicago to Jamaica with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $158	Free Cancellation	Rating 7.8 8,667 reviews	Search Delta flights
Frontier	PriceFrom $172	Free Cancellation	Rating 5.5 2,520 reviews	Search Frontier flights
JetBlue	PriceFrom $301	Free Cancellation	Rating 7.1 3,063 reviews	Search JetBlue flights
American Airlines	PriceFrom $312	Free Cancellation	Rating 7.0 12,189 reviews	Search American Airlines flights
United Airlines	PriceFrom $317	Free Cancellation	Rating 7.3 10,415 reviews	Search United Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 7.9 4,210 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jamaica?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Jamaica. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?

Flights from Chicago to Jamaica with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Jamaica?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Jamaica.

I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Jamaica from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Jamaica trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

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Complete your trip

Feeling lucky

Popular cities in Jamaica

Flights to Montego Bayfrom $241

Flights to Kingstonfrom $409

Flights to Ocho Rios

Cheap flights from Chicago to Jamaica from $178

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Jamaica departing on 11/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Chicago to Jamaica

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

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American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets

Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

See travel insights to Jamaica from

How to get the cheapest flight ticket from Chicago to Jamaica

What is the cheapest month to fly to Jamaica?

What is the cheapest day to depart on your flight to Jamaica?

What is the cheapest Chicago to Jamaica flight route?

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

What cabin class options are available on Chicago to Jamaica flights?

Can stopping save me money on Chicago to Jamaica flights?

What is the cheapest airline that flies from Chicago to Jamaica?

What airlines fly to Jamaica?

Cheap Chicago to Jamaica flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Jamaica

Frequently asked questions about flying from Chicago to Jamaica

Best airlines flying from Chicago to Jamaica

Compare and see reviews for airlines that fly from Chicago to Jamaica with momondo

Why use momondo?

An easier way to manage your Jamaica trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Jamaica

Popular cities in Jamaica

Popular flights according to clicks in the last 7 days on momondo

Chicago flight routes

According to popular flight searches on momondo this year

Jamaica flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Jamaica

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Jamaica

List of cabin classes available on flights landing in Jamaica. Availability may vary depending on flight origin and airline.

Complete your trip to Jamaica

Explore popular destinations other users love

According to popular flight searches on momondo this year