How many flights depart from Chicago to Jamaica on average per week?

As of June 2026, there are 6 flights per week flying from Chicago to Jamaica. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.

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 71% 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, Southwest, and American Airlines 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 June 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.

$138 Cheap Flights from Chicago to Jamaica in 2026

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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.

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

3:59 pm - 11:44 pm

MBJ

ORD

8h 45m

1 stop

$346JetBlue

Tue, Nov 3 - Tue, Nov 10

5:00 am - 12:42 pm

ORD

MBJ

6h 42m

1 stop

3:14 pm - 6:55 pm

MBJ

ORD

4h 41mnonstop

$347American Airlines

Wed, Nov 18 - Wed, Nov 25

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

3:59 pm - 11:44 pm

MBJ

ORD

8h 45m

1 stop

$348JetBlue

Tue, Nov 3 - Tue, Nov 10

6:05 am - 3:34 pm

MDW

MBJ

9h 29m

1 stop

1:09 pm - 10:36 pm

MBJ

MDW

9h 27m

1 stop

$352Delta

Sun, Aug 30 - Wed, Sep 2

6:40 am - 1:01 pm

ORD

MBJ

6h 21m

1 stop

4:59 pm - 12:02 am

MBJ

ORD

7h 03m

1 stop

$352Delta

Sun, Aug 16 - Thu, Aug 20

6:00 am - 12:07 pm

MDW

MBJ

6h 07m

1 stop

1:32 pm - 8:45 am

MBJ

MDW

19h 13m

2 stops

$357Delta

Tue, Oct 13 - Thu, Oct 15

6:00 am - 12:21 pm

MDW

MBJ

6h 21m

1 stop

1:32 pm - 10:03 pm

MBJ

MDW

8h 31m

1 stop

$452Frontier

Tue, Jun 30 - Wed, Jul 8

10:10 am - 2:00 pm

MDW

MBJ

3h 50mnonstop

2:30 pm - 11:15 pm

MBJ

MDW

8h 45m

1 stop

$456Southwest

Sat, Jul 4 - Sat, Jul 11

5:05 am - 1:30 pm

MDW

MBJ

8h 25m

1 stop

2:20 pm - 10:05 pm

MBJ

MDW

7h 45m

1 stop

$457Southwest

Sat, Jul 25 - Wed, Jul 29

2:35 pm - 11:37 pm

ORD

KIN

9h 02m

1 stop

3:05 pm - 2:55 pm

KIN

ORD

23h 50m

1 stop

$501Multiple Airlines

Thu, Jul 16 - Mon, Jul 20

Copa Airlines flights from Chicago to Jamaica

Our best Copa Airlines deals on Chicago to Jamaica flight tickets

Copa Airlines

Jul 22

ORD3:21 pmChicago O'Hare Intl

22h 33m

1 stop

KIN1:54 pmKingston Norman Manley

Jul 28

KIN2:56 pmKingston Norman Manley

13h 04m

1 stop

ORD4:00 amChicago O'Hare Intl

$512

Copa Airlines

Jul 1

ORD3:21 pmChicago O'Hare Intl

22h 33m

1 stop

KIN1:54 pmKingston Norman Manley

Jul 7

KIN2:56 pmKingston Norman Manley

13h 04m

1 stop

ORD4:00 amChicago O'Hare Intl

$530

Copa Airlines

Jun 5

ORD3:21 pmChicago O'Hare Intl

19h 54m

1 stop

MBJ11:15 amMontego Bay Sangster Intl

Jun 10

MBJ12:22 pmMontego Bay Sangster Intl

15h 38m

1 stop

ORD4:00 amChicago O'Hare Intl

$534

Air Canada flights from Chicago to Jamaica

Our best Air Canada deals on Chicago to Jamaica flight tickets

Air Canada

Jun 13

ORD8:20 pmChicago O'Hare Intl

15h 00m

1 stop

MBJ11:20 amMontego Bay Sangster Intl

Jun 17

MBJ12:30 pmMontego Bay Sangster Intl

24h 52m

1 stop

ORD1:22 pmChicago O'Hare Intl

$453

Air Canada

Jun 13

ORD3:40 pmChicago O'Hare Intl

19h 40m

2 stops

MBJ11:20 amMontego Bay Sangster Intl

Jun 15

MBJ12:30 pmMontego Bay Sangster Intl

20h 30m

1 stop

ORD9:00 amChicago O'Hare Intl

$457

Air Canada

Jun 14

ORD8:20 pmChicago O'Hare Intl

15h 00m

1 stop

MBJ11:20 amMontego Bay Sangster Intl

Jun 18

MBJ12:30 pmMontego Bay Sangster Intl

26h 25m

1 stop

ORD2:55 pmChicago O'Hare Intl

$464

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 11/3

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Tue 11/10

3:59 pm-11:44 pm

1 stop8h 45m

$346

Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/18

5:00 am-12:42 pm

1 stop6h 42m

Montego Bay Sangster Intl

Wed 11/25

3:14 pm-6:55 pm

Nonstop4h 41m

$347

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 11/3

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Tue 11/10

3:59 pm-11:44 pm

1 stop8h 45m

$348

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/30

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Wed 9/2

1:09 pm-10:36 pm

1 stop9h 27m

$352

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

6:40 am-1:01 pm

1 stop6h 21m

Montego Bay Sangster Intl

Thu 8/20

4:59 pm-12:02 am

1 stop7h 03m

$352

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 10/13

6:00 am-12:07 pm

1 stop6h 07m

Montego Bay Sangster Intl

Thu 10/15

1:32 pm-8:45 am

2 stops19h 13m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 6/30

6:00 am-12:21 pm

1 stop6h 21m

Montego Bay Sangster Intl

Wed 7/8

1:32 pm-10:03 pm

1 stop8h 31m

$452

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/4

10:10 am-2:00 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 7/11

2:30 pm-11:15 pm

1 stop8h 45m

$456

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/25

5:05 am-1:30 pm

1 stop8h 25m

Montego Bay Sangster Intl

Wed 7/29

2:20 pm-10:05 pm

1 stop7h 45m

$457

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 7/16

2:35 pm-11:37 pm

1 stop9h 02m

Kingston Norman Manley

Mon 7/20

3:05 pm-2:55 pm

1 stop23h 50m

$501

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

Other information

What is the cheapest month to fly to Jamaica?

The cheapest month to fly to Jamaica from Chicago is in December. Flight prices, which tend to average around $84, 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 December, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $93.

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 $493. 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 $638.

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 $531 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 $465 on momondo.

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

There are 2 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?

You could potentially save up to 14% on your flight if you consider stops on a Chicago to Jamaica flight.

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	$148
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 $148. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $408.

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 June 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 (73.09% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (18.24%), Airbus A321-100/200 (4.19%), and Boeing 737 (2.99%).

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 2,919 reviews	Search Frontier flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 8,398 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 2,982 reviews	Search JetBlue flights
United Airlines	PriceFrom $302	Free Cancellation	Rating 7.4 9,771 reviews	Search United Airlines flights
American Airlines	PriceFrom $319	Free Cancellation	Rating 7.1 11,640 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 8.0 4,254 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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Popular cities in Jamaica

Flights to Montego Bayfrom $302

Flights to Kingstonfrom $373

Flights to Ocho Rios

Cheap flights from Chicago to Jamaica from $138

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 8/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Copa Airlines flights from Chicago to Jamaica

Our best Copa Airlines deals on Chicago to Jamaica flight tickets

Air Canada flights from Chicago to Jamaica

Our best Air Canada deals on Chicago to Jamaica flight tickets

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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?

How many flights depart from Chicago to Jamaica on average per week?

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

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