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 is the cheapest airline that flies from Chicago to Jamaica?

JetBlue, American Airlines, and Delta 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 70% 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 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.

$158 Cheap Flights from Chicago to Jamaica in 2026

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.

7:00 am - 5:33 pm

ORD

MBJ

10h 33m

1 stop

12:55 pm - 11:44 pm

MBJ

ORD

10h 49m

1 stop

$355JetBlue

Fri, Aug 28 - Mon, Aug 31

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

3:59 pm - 11:44 pm

MBJ

ORD

8h 45m

1 stop

$361JetBlue

Wed, Nov 11 - Tue, Nov 17

7:00 am - 5:33 pm

ORD

MBJ

10h 33m

1 stop

12:55 pm - 11:44 pm

MBJ

ORD

10h 49m

1 stop

$364JetBlue

Fri, Aug 28 - Mon, Aug 31

6:05 am - 12:27 pm

MDW

MBJ

6h 22m

1 stop

1:32 pm - 10:03 pm

MBJ

MDW

8h 31m

1 stop

$452Frontier

Tue, Aug 4 - Wed, Aug 12

6:00 am - 12:59 pm

ORD

KIN

6h 59m

1 stop

2:00 pm - 12:35 am

KIN

ORD

10h 35m

1 stop

$456American Airlines

Sun, Aug 23 - Sat, Aug 29

5:22 am - 4:13 pm

ORD

KIN

10h 51m

2 stops

7:30 am - 5:52 pm

KIN

ORD

10h 22m

2 stops

$461American Airlines

Tue, Oct 20 - Wed, Oct 28

6:00 am - 12:21 pm

MDW

MBJ

6h 21m

1 stop

1:26 pm - 10:11 pm

MBJ

MDW

8h 45m

1 stop

$472Frontier

Fri, Aug 21 - Tue, Aug 25

3:21 pm - 1:54 pm

ORD

KIN

22h 33m

1 stop

2:56 pm - 4:00 am

KIN

ORD

13h 04m

1 stop

$510Copa Airlines

Sat, Jul 4 - Tue, Jul 7

6:05 am - 8:13 pm

MDW

KIN

14h 08m

1 stop

9:13 am - 10:36 pm

KIN

MDW

13h 23m

1 stop

$524Delta

Fri, Aug 21 - Sun, Aug 23

6:58 pm - 8:03 pm

MDW

KIN

25h 05m

2 stops

9:13 am - 9:17 am

KIN

MDW

24h 04m

2 stops

$529Delta

Tue, Jul 28 - Wed, Aug 5

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JetBlue flights from Chicago to Jamaica

Our best JetBlue deals on Chicago to Jamaica flight tickets

JetBlue

Aug 28

ORD7:00 amChicago O'Hare Intl

10h 33m

1 stop

MBJ5:33 pmMontego Bay Sangster Intl

Aug 31

MBJ12:55 pmMontego Bay Sangster Intl

10h 49m

1 stop

ORD11:44 pmChicago O'Hare Intl

$355

JetBlue

Nov 11

ORD7:00 amChicago O'Hare Intl

6h 54m

1 stop

MBJ2:54 pmMontego Bay Sangster Intl

Nov 17

MBJ3:59 pmMontego Bay Sangster Intl

8h 45m

1 stop

ORD11:44 pmChicago O'Hare Intl

$361

JetBlue

Aug 28

ORD7:00 amChicago O'Hare Intl

10h 33m

1 stop

MBJ5:33 pmMontego Bay Sangster Intl

Aug 31

MBJ12:55 pmMontego Bay Sangster Intl

10h 49m

1 stop

ORD11:44 pmChicago O'Hare Intl

$364

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets

Frontier

Aug 4

MDW6:05 amChicago Midway

6h 22m

1 stop

MBJ12:27 pmMontego Bay Sangster Intl

Aug 12

MBJ1:32 pmMontego Bay Sangster Intl

8h 31m

1 stop

MDW10:03 pmChicago Midway

$452

Frontier

Aug 21

MDW6:00 amChicago Midway

6h 21m

1 stop

MBJ12:21 pmMontego Bay Sangster Intl

Aug 25

MBJ1:26 pmMontego Bay Sangster Intl

8h 45m

1 stop

MDW10:11 pmChicago Midway

$472

Frontier

Jul 28

MDW12:11 pmChicago Midway

24h 16m

1 stop

MBJ12:27 pmMontego Bay Sangster Intl

Aug 2

MBJ1:39 pmMontego Bay Sangster Intl

8h 24m

1 stop

MDW10:03 pmChicago Midway

$473

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 8/28

7:00 am-5:33 pm

1 stop10h 33m

Montego Bay Sangster Intl

Mon 8/31

12:55 pm-11:44 pm

1 stop10h 49m

$355

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/11

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Tue 11/17

3:59 pm-11:44 pm

1 stop8h 45m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 8/28

7:00 am-5:33 pm

1 stop10h 33m

Montego Bay Sangster Intl

Mon 8/31

12:55 pm-11:44 pm

1 stop10h 49m

$364

Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 8/4

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Wed 8/12

1:32 pm-10:03 pm

1 stop8h 31m

$452

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 8/23

6:00 am-12:59 pm

1 stop6h 59m

Kingston Norman Manley

Sat 8/29

2:00 pm-12:35 am

1 stop10h 35m

$456

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 10/20

5:22 am-4:13 pm

2 stops10h 51m

Kingston Norman Manley

Wed 10/28

7:30 am-5:52 pm

2 stops10h 22m

$461

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 8/21

6:00 am-12:21 pm

1 stop6h 21m

Montego Bay Sangster Intl

Tue 8/25

1:26 pm-10:11 pm

1 stop8h 45m

$472

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 7/4

3:21 pm-1:54 pm

1 stop22h 33m

Kingston Norman Manley

Tue 7/7

2:56 pm-4:00 am

1 stop13h 04m

$510

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 8/21

6:05 am-8:13 pm

1 stop14h 08m

Kingston Norman Manley

Sun 8/23

9:13 am-10:36 pm

1 stop13h 23m

$524

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 7/28

6:58 pm-8:03 pm

2 stops25h 05m

Kingston Norman Manley

Wed 8/5

9:13 am-9:17 am

2 stops24h 04m

$529

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 $490. 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 $637.

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 $526 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 $466 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 20% 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 $450.

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 (75.21% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (14.87%), Airbus A321-100/200 (4.62%), and Boeing 737 (3.59%).

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 2,880 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.8 8,410 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 2,983 reviews	Search JetBlue flights
United Airlines	PriceFrom $297	Free Cancellation	Rating 7.4 9,859 reviews	Search United Airlines flights
American Airlines	PriceFrom $318	Free Cancellation	Rating 7.1 11,684 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 7.9 4,237 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 $323

Flights to Kingstonfrom $384

Flights to Ocho Rios

Cheap flights from Chicago to Jamaica from $158

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 8/29. 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

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JetBlue flights from Chicago to Jamaica

Our best JetBlue 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?

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