What airlines fly to Jamaica?

American Airlines, United Airlines and Delta 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 64% 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?

Delta, JetBlue, and Air Canada 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 September 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.

$175 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.

7:05 am - 5:20 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

33h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

2:18 pm - 9:40 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

8h 22m1 stop Atlanta Hartsfield-Jackson

$430Multiple Airlines

Tue, Dec 1 - Fri, Dec 4

3:50 pm - 1:13 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

20h 23m1 stop Atlanta Hartsfield-Jackson

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

22h 11m1 stop Atlanta Hartsfield-Jackson

$431Frontier

Thu, Dec 3 - Mon, Dec 7

6:42 pm - 3:08 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

19h 26m1 stop Atlanta Hartsfield-Jackson

4:43 pm - 5:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

26h 04m1 stop Atlanta Hartsfield-Jackson

$431Frontier

Thu, Nov 5 - Sun, Nov 8

7:15 am - 2:28 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 13m1 stop Atlanta Hartsfield-Jackson

6:20 pm - 7:58 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

26h 38m1 stop Toronto Pearson Intl

$435Multiple Airlines

Sat, Oct 31 - Sat, Nov 7

9:40 am - 2:52 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 12mnonstop

3:49 pm - 7:45 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 56mnonstop

$436American Airlines

Sun, Nov 15 - Fri, Nov 20

9:40 am - 2:52 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 12mnonstop

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

4h 50mnonstop

$436American Airlines

Mon, Nov 9 - Thu, Nov 12

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

$468United Airlines

Wed, Oct 28 - Sun, Nov 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

$468United Airlines

Tue, Nov 17 - Sun, Nov 22

7:00 am - 2:57 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

6h 57m1 stop Fort Lauderdale

1:07 pm - 11:36 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

11h 29m1 stop Fort Lauderdale

$472JetBlue

Mon, Nov 9 - Sat, Nov 14

7:00 am - 2:57 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

6h 57m1 stop Fort Lauderdale

3:00 pm - 11:38 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 38m1 stop Fort Lauderdale

$472JetBlue

Tue, Nov 17 - Sun, Nov 22

Cheap last minute flights

Enter your travel dates to find the best prices.

7:21 pm - 2:27 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

19h 06m1 stop Atlanta Hartsfield-Jackson

3:48 pm - 9:21 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

17h 33m1 stop Atlanta Hartsfield-Jackson

$433Frontier

Sat, Oct 3 - Sat, Oct 10

7:28 pm - 12:02 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

16h 34m1 stop Atlanta Hartsfield-Jackson

3:48 pm - 6:31 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

26h 43m1 stop Atlanta Hartsfield-Jackson

$470Frontier

Fri, Oct 2 - Fri, Oct 9

6:15 am - 11:55 amMDW Chicago Midway-MBJ Montego Bay Sangster Intl

5h 40m1 stop Orlando

3:45 pm - 10:55 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

8h 10m1 stop Orlando

$482Southwest

Tue, Sep 29 - Mon, Nov 2

6:15 am - 11:55 amMDW Chicago Midway-MBJ Montego Bay Sangster Intl

5h 40m1 stop Orlando

3:25 pm - 9:25 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

7h 00m1 stop Baltimore/Washington

$482Southwest

Tue, Sep 29 - Tue, Nov 3

3:40 pm - 1:55 pmORD Chicago O'Hare Intl-KIN Kingston Norman Manley

22h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

3:05 pm - 6:46 pmKIN Kingston Norman Manley-ORD Chicago O'Hare Intl

27h 41m2 stops Toronto Pearson Intl Ottawa

$545Air Canada

Wed, Sep 30 - Wed, Oct 7

7:21 pm - 2:27 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

19h 06m1 stop Atlanta Hartsfield-Jackson

12:30 pm - 7:44 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

19h 14m2 stops Toronto Pearson Intl Ottawa

$552Multiple Airlines

Sat, Oct 3 - Sat, Oct 10

5:20 am - 1:09 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 49m1 stop Charlotte Douglas

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

4h 50mnonstop

$576American Airlines

Tue, Sep 29 - Tue, Nov 3

6:45 am - 1:09 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

6h 24m1 stop Charlotte Douglas

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

4h 50mnonstop

$576American Airlines

Tue, Sep 29 - Mon, Nov 2

6:05 am - 1:01 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

6h 56m1 stop Atlanta Hartsfield-Jackson

8:00 am - 4:19 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

9h 19m1 stop Atlanta Hartsfield-Jackson

$766Delta

Tue, Sep 29 - Tue, Dec 29

5:30 am - 11:48 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

6h 18m1 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

$811Delta

Thu, Oct 1 - Thu, Oct 8

Cheap direct flights

Enter your travel dates to find the best prices.

9:40 am - 2:52 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 12mnonstop

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

4h 50mnonstop

$436American Airlines

Mon, Nov 9 - Thu, Nov 12

9:40 am - 2:52 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 12mnonstop

3:49 pm - 7:45 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 56mnonstop

$436American Airlines

Sun, Nov 15 - Fri, Nov 20

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

$437American Airlines

Sun, Jan 31 - Wed, Feb 3

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

$468United Airlines

Tue, Dec 8 - Fri, Dec 11

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

$468United Airlines

Tue, Nov 10 - Sat, Nov 14

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

$468United Airlines

Wed, Oct 28 - Thu, Oct 29

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

$549Southwest

Sat, Jan 30 - Sat, Feb 6

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

4h 08mnonstop

3:59 pm - 7:46 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 47mnonstop

$592Multiple Airlines

Mon, Oct 26 - Sun, Nov 1

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

4h 08mnonstop

3:59 pm - 7:46 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 47mnonstop

$594Multiple Airlines

Mon, Oct 26 - Sun, Nov 1

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

$607Southwest

Sat, Jan 23 - Sat, Jan 30

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Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets

Southwest

Sep 29

MDW6:15 amChicago Midway

5h 40m

1 stop

MBJ11:55 amMontego Bay Sangster Intl

Nov 3

MBJ3:25 pmMontego Bay Sangster Intl

7h 00m

1 stop

MDW9:25 pmChicago Midway

$482

Southwest

Nov 15

MDW5:05 amChicago Midway

8h 20m

1 stop

MBJ2:25 pmMontego Bay Sangster Intl

Nov 20

MBJ1:00 pmMontego Bay Sangster Intl

11h 10m

1 stop

MDW11:10 pmChicago Midway

$512

Southwest

Nov 15

MDW6:30 pmChicago Midway

16h 30m

2 stops

MBJ12:00 pmMontego Bay Sangster Intl

Nov 20

MBJ3:45 pmMontego Bay Sangster Intl

8h 15m

1 stop

MDW11:00 pmChicago Midway

$517

Copa Airlines flights from Chicago to Jamaica

Our best Copa Airlines deals on Chicago to Jamaica flight tickets

Copa Airlines

Oct 23

ORD3:20 pmChicago O'Hare Intl

19h 57m

1 stop

MBJ11:17 amMontego Bay Sangster Intl

Oct 25

MBJ12:24 pmMontego Bay Sangster Intl

12h 41m

1 stop

ORD1:05 amChicago O'Hare Intl

$470

Copa Airlines

Feb 20

ORD2:13 pmChicago O'Hare Intl

20h 02m

1 stop

MBJ11:15 amMontego Bay Sangster Intl

Feb 27

MBJ2:28 pmMontego Bay Sangster Intl

10h 43m

1 stop

ORD12:11 amChicago O'Hare Intl

$471

Copa Airlines

Oct 4

ORD3:20 pmChicago O'Hare Intl

19h 57m

1 stop

MBJ11:17 amMontego Bay Sangster Intl

Oct 6

MBJ12:22 pmMontego Bay Sangster Intl

12h 35m

1 stop

ORD12:57 amChicago O'Hare Intl

$510

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

Tue 12/1

7:05 am-5:20 pm

2 stops33h 15m

Montego Bay Sangster Intl

Fri 12/4

2:18 pm-9:40 pm

1 stop8h 22m

$430

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 12/3

3:50 pm-1:13 pm

1 stop20h 23m

Montego Bay Sangster Intl

Mon 12/7

2:22 pm-11:33 am

1 stop22h 11m

$431

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 11/5

6:42 pm-3:08 pm

1 stop19h 26m

Montego Bay Sangster Intl

Sun 11/8

4:43 pm-5:47 pm

1 stop26h 04m

$431

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sat 10/31

7:15 am-2:28 pm

1 stop7h 13m

Montego Bay Sangster Intl

Sat 11/7

6:20 pm-7:58 pm

1 stop26h 38m

$435

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Sun 11/15

9:40 am-2:52 pm

Nonstop4h 12m

Montego Bay Sangster Intl

Fri 11/20

3:49 pm-7:45 pm

Nonstop4h 56m

$436

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Mon 11/9

9:40 am-2:52 pm

Nonstop4h 12m

Montego Bay Sangster Intl

Thu 11/12

3:56 pm-7:46 pm

Nonstop4h 50m

$436

Quickest round-trip

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Wed 10/28

8:40 am-12:48 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Sun 11/1

2:54 pm-6:20 pm

Nonstop4h 26m

$468

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Tue 11/17

8:40 am-1:48 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Sun 11/22

2:54 pm-6:20 pm

Nonstop4h 26m

$468

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Mon 11/9

7:00 am-2:57 pm

1 stop6h 57m

Montego Bay Sangster Intl

Sat 11/14

1:07 pm-11:36 pm

1 stop11h 29m

$472

ChicagoMontego Bay

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

ORDMBJ

Chicago O'Hare Intl

Tue 11/17

7:00 am-2:57 pm

1 stop6h 57m

Montego Bay Sangster Intl

Sun 11/22

3:00 pm-11:38 pm

1 stop9h 38m

$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 $474, 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 October is also cheap. Prices for this month can be found on momondo for an average of $507.

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 $476. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday 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 $596.

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 $547 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 $462 on momondo.

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

There are 4 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	$175
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 $175. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $430.

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 September 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 (84.55% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (5.45%), Boeing 737 (4.18%), and Boeing 737 MAX 8 (3.09%).

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
Frontier	PriceFrom $144	Free Cancellation	Rating 5.6 2,572 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.8 8,605 reviews	Search Delta flights
JetBlue	PriceFrom $301	Free Cancellation	Rating 7.1 3,038 reviews	Search JetBlue flights
United Airlines	PriceFrom $302	Free Cancellation	Rating 7.4 10,247 reviews	Search United Airlines flights
American Airlines	PriceFrom $315	Free Cancellation	Rating 7.0 12,098 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 8.0 4,200 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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Find better results for your trip to Jamaica

Popular cities

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Complete your trip

Feeling lucky

Popular cities in Jamaica

Flights to Montego Bayfrom $300

Flights to Kingstonfrom $429

Flights to Ocho Rios

Cheap flights from Chicago to Jamaica from $175

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 10/23. 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

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

Filter for what you want

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Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets

Copa Airlines flights from Chicago to Jamaica

Our best Copa Airlines 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