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

JetBlue, Delta, and Frontier are the most popular carriers operating from Chicago to Jamaica

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.

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.

$177 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:45 am - 12:50 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

27h 05m1 stop Toronto Pearson Intl

6:50 pm - 2:52 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

21h 02m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

$468Air Canada

Sun, Nov 29 - Thu, Jan 14

10:57 am - 1:25 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

25h 28m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

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

8h 20m1 stop Atlanta Hartsfield-Jackson

$468Multiple Airlines

Sat, Dec 5 - Thu, Dec 10

9:06 pm - 2:22 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

16h 16m1 stop Charlotte Douglas

11:05 am - 6:25 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

8h 20m1 stop Miami

$469American Airlines

Sun, Dec 6 - Wed, Dec 9

9:06 pm - 12:02 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

13h 56m1 stop Charlotte Douglas

1:02 pm - 12:01 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

11h 59m1 stop Charlotte Douglas

$469American Airlines

Mon, Nov 9 - Thu, Nov 12

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

5:45 am - 2:39 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 54m1 stop Houston George Bush Intcntl

1:25 pm - 9:33 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 08m1 stop Newark

$469United Airlines

Sun, Dec 6 - Fri, Dec 11

5:30 am - 3:25 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

8h 55m1 stop Atlanta Hartsfield-Jackson

3:25 pm - 9:33 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

19h 08m1 stop Boston Logan Intl

$470Delta

Mon, Jan 25 - Tue, Feb 2

7:00 pm - 12:55 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

16h 55m1 stop Atlanta Hartsfield-Jackson

3:25 pm - 9:33 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

19h 08m1 stop Boston Logan Intl

$470Delta

Sun, Jan 24 - Tue, Feb 2

3:50 pm - 1:17 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

20h 27m1 stop Atlanta Hartsfield-Jackson

2:22 pm - 11:33 amMBJ Montego Bay Sangster Intl-MDW Chicago Midway

22h 11m1 stop Atlanta Hartsfield-Jackson

$472Frontier

Sun, Dec 6 - Mon, Dec 14

12:28 pm - 1:17 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

23h 49m1 stop Atlanta Hartsfield-Jackson

2:22 pm - 2:55 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

25h 33m1 stop Atlanta Hartsfield-Jackson

$472Frontier

Sat, Dec 5 - Sat, Dec 12

Cheap last minute flights

Enter your travel dates to find the best prices.

6:24 am - 2:33 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

8h 09m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 6:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

26h 57m1 stop Atlanta Hartsfield-Jackson

$507Frontier

Sun, Oct 25 - Sat, Oct 31

3:40 pm - 11:50 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

20h 10m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

1:50 pm - 8:00 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

19h 10m2 stops Toronto Pearson Intl Ottawa

$552Air Canada

Sat, Oct 24 - Thu, Nov 19

9:21 pm - 11:50 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

14h 29m1 stop Toronto Pearson Intl

5:20 pm - 12:07 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

18h 47m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$600Air Canada

Sun, Oct 25 - Sat, Oct 31

6:21 am - 2:33 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

8h 12m1 stop Atlanta Hartsfield-Jackson

3:43 pm - 11:25 amMBJ Montego Bay Sangster Intl-MDW Chicago Midway

19h 42m2 stops Atlanta Hartsfield-Jackson Dallas/Fort Worth

$621Frontier

Sat, Oct 24 - Thu, Oct 29

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

4h 08mnonstop

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

4h 26mnonstop

$623United Airlines

Sun, Oct 25 - Sat, Oct 31

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

4h 08mnonstop

2:45 pm - 12:45 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

10h 00m1 stop Houston George Bush Intcntl

$633United Airlines

Sun, Oct 25 - Sat, Oct 31

7:00 am - 2:05 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 05m1 stop Fort Lauderdale

2:53 pm - 11:57 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 04m1 stop Fort Lauderdale

$655JetBlue

Wed, Oct 21 - Sun, Oct 25

5:45 am - 11:50 amMDW Chicago Midway-MBJ Montego Bay Sangster Intl

6h 05m1 stop Orlando

12:00 pm - 9:40 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

9h 40m1 stop Orlando

$664Southwest

Tue, Oct 20 - Fri, Oct 23

5:45 am - 11:50 amMDW Chicago Midway-MBJ Montego Bay Sangster Intl

6h 05m1 stop Orlando

12:00 pm - 11:55 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

11h 55m2 stops Orlando Nashville Intl

$681Southwest

Tue, Oct 20 - Fri, Oct 23

6:04 am - 11:51 amMDW Chicago Midway-MBJ Montego Bay Sangster Intl

5h 47m1 stop Atlanta Hartsfield-Jackson

1:16 pm - 10:33 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

9h 17m1 stop Atlanta Hartsfield-Jackson

$697Delta

Tue, Oct 20 - Fri, Oct 23

Cheap direct flights

Enter your travel dates to find the best prices.

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

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

$486American Airlines

Mon, Jan 25 - Tue, Feb 2

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

$486American Airlines

Sun, Jan 24 - Fri, Feb 5

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

$496United Airlines

Tue, Dec 1 - Tue, Dec 8

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

$496United Airlines

Mon, Nov 9 - Wed, Nov 18

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

$496United Airlines

Tue, Dec 1 - Fri, Dec 4

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

$589Southwest

Sat, Jan 30 - Sat, Feb 6

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

$716Southwest

Sat, Jan 9 - Sat, Jan 16

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

$1,073Virgin Australia

Sun, Nov 1 - Wed, Nov 4

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

$1,215Virgin Australia

Mon, Jan 11 - Fri, Jan 15

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American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets

American Airlines

Feb 8

ORD10:05 amChicago O'Hare Intl

4h 13m

MBJ3:18 pmMontego Bay Sangster Intl

Feb 9

MBJ6:05 pmMontego Bay Sangster Intl

8h 00m

1 stop

ORD1:05 amChicago O'Hare Intl

$467

American Airlines

Feb 21

ORD8:52 pmChicago O'Hare Intl

12h 20m

1 stop

MBJ10:12 amMontego Bay Sangster Intl

Feb 26

MBJ6:03 pmMontego Bay Sangster Intl

7h 56m

1 stop

ORD12:59 amChicago O'Hare Intl

$472

American Airlines

Nov 9

ORD9:40 amChicago O'Hare Intl

4h 12m

MBJ2:52 pmMontego Bay Sangster Intl

Nov 14

MBJ1:10 pmMontego Bay Sangster Intl

10h 20m

1 stop

ORD10:30 pmChicago O'Hare Intl

$491

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets

Frontier

Dec 5

MDW12:28 pmChicago Midway

23h 49m

1 stop

MBJ1:17 pmMontego Bay Sangster Intl

Dec 13

MBJ2:22 pmMontego Bay Sangster Intl

25h 33m

1 stop

MDW2:55 pmChicago Midway

$472

Frontier

Nov 9

MDW6:08 amChicago Midway

8h 00m

1 stop

MBJ3:08 pmMontego Bay Sangster Intl

Nov 15

MBJ4:43 pmMontego Bay Sangster Intl

8h 04m

1 stop

MDW11:47 pmChicago Midway

$488

Frontier

Nov 8

ORD10:19 amChicago O'Hare Intl

27h 49m

1 stop

MBJ3:08 pmMontego Bay Sangster Intl

Nov 12

MBJ4:43 pmMontego Bay Sangster Intl

17h 31m

1 stop

ORD9:14 amChicago O'Hare Intl

$489

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

Sun 11/29

8:45 am-12:50 pm

1 stop27h 05m

Montego Bay Sangster Intl

Thu 1/14

6:50 pm-2:52 pm

2 stops21h 02m

$468

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sat 12/5

10:57 am-1:25 pm

2 stops25h 28m

Montego Bay Sangster Intl

Thu 12/10

2:22 pm-9:42 pm

1 stop8h 20m

$468

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sun 12/6

9:06 pm-2:22 pm

1 stop16h 16m

Montego Bay Sangster Intl

Wed 12/9

11:05 am-6:25 pm

1 stop8h 20m

$469

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Mon 11/9

9:06 pm-12:02 pm

1 stop13h 56m

Montego Bay Sangster Intl

Thu 11/12

1:02 pm-12:01 am

1 stop11h 59m

$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

Quickest round-trip

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sun 12/6

5:45 am-2:39 pm

1 stop7h 54m

Montego Bay Sangster Intl

Fri 12/11

1:25 pm-9:33 pm

1 stop9h 08m

$469

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Mon 1/25

5:30 am-3:25 pm

1 stop8h 55m

Montego Bay Sangster Intl

Tue 2/2

3:25 pm-9:33 am

1 stop19h 08m

$470

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sun 1/24

7:00 pm-12:55 pm

1 stop16h 55m

Montego Bay Sangster Intl

Tue 2/2

3:25 pm-9:33 am

1 stop19h 08m

$470

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Sun 12/6

3:50 pm-1:17 pm

1 stop20h 27m

Montego Bay Sangster Intl

Mon 12/14

2:22 pm-11:33 am

1 stop22h 11m

$472

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Sat 12/5

12:28 pm-1:17 pm

1 stop23h 49m

Montego Bay Sangster Intl

Sat 12/12

2:22 pm-2:55 pm

1 stop25h 33m

$472

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	$177
Fastest flight time	3h 55m
Direct flights	Every day
Airports in Jamaica	11 airports

The best one-way flight to Jamaica from Chicago in the past 72 hours is $177. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $468.

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

Direct flights go from Chicago to Jamaica every day.

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 8,651 reviews	Search Delta flights
Frontier	PriceFrom $172	Free Cancellation	Rating 5.5 2,527 reviews	Search Frontier flights
JetBlue	PriceFrom $301	Free Cancellation	Rating 7.1 3,059 reviews	Search JetBlue flights
American Airlines	PriceFrom $312	Free Cancellation	Rating 7.0 12,175 reviews	Search American Airlines flights
United Airlines	PriceFrom $317	Free Cancellation	Rating 7.3 10,388 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.

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Complete your trip

Feeling lucky

Popular cities in Jamaica

Flights to Montego Bayfrom $239

Flights to Kingstonfrom $403

Flights to Ocho Rios

Cheap flights from Chicago to Jamaica from $177

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

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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

Frontier flights from Chicago to Jamaica

Our best Frontier 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