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

1 flights are operational daily from Chicago to Jamaica as of June 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

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

As of June 2026, there are 8 flights per week flying from Chicago to Jamaica. The most common day of the week flights depart is Sat, with 25% 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 69% 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?

JetBlue, American 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 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.

$160 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 - 2:54 pm

ORD

MBJ

6h 54m

1 stop

2:00 pm - 11:44 pm

MBJ

ORD

10h 44m

1 stop

$384JetBlue

Tue, Nov 3 - Tue, Nov 10

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

2:00 pm - 11:44 pm

MBJ

ORD

10h 44m

1 stop

$394JetBlue

Tue, Nov 3 - Thu, Nov 5

6:00 am - 4:02 pm

ORD

KIN

10h 02m

1 stop

1:08 pm - 11:32 pm

KIN

ORD

10h 24m

1 stop

$398American Airlines

Sun, Sep 13 - Thu, Sep 17

5:00 am - 4:02 pm

ORD

KIN

11h 02m

2 stops

1:08 pm - 11:56 pm

KIN

ORD

10h 48m

2 stops

$403American Airlines

Sun, Sep 13 - Thu, Sep 17

6:05 am - 1:01 pm

MDW

MBJ

6h 56m

1 stop

1:09 pm - 10:36 pm

MBJ

MDW

9h 27m

1 stop

$448Delta

Sun, Aug 16 - Fri, Aug 21

7:25 am - 1:31 pm

MDW

MBJ

6h 06m

1 stop

2:49 pm - 9:58 pm

MBJ

MDW

7h 09m

1 stop

$452Frontier

Sat, Sep 19 - Sat, Sep 26

12:46 pm - 8:13 pm

MDW

KIN

7h 27m

1 stop

9:13 am - 4:15 pm

KIN

MDW

7h 02m

1 stop

$464Delta

Fri, Aug 21 - Sun, Aug 23

6:05 am - 12:24 pm

MDW

MBJ

6h 19m

1 stop

1:32 pm - 10:03 pm

MBJ

MDW

8h 31m

1 stop

$472Frontier

Sun, Aug 2 - Wed, Aug 5

5:00 am - 1:30 pm

MDW

MBJ

8h 30m

2 stops

2:15 pm - 9:30 pm

MBJ

MDW

7h 15m

1 stop

$473Southwest

Sun, Aug 16 - Fri, Aug 21

5:10 am - 1:30 pm

MDW

MBJ

8h 20m

1 stop

12:55 pm - 9:00 pm

MBJ

MDW

8h 05m

1 stop

$513Southwest

Sun, Aug 16 - Wed, Aug 19

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets

Frontier

Sep 19

MDW7:25 amChicago Midway

6h 06m

1 stop

MBJ1:31 pmMontego Bay Sangster Intl

Sep 26

MBJ2:49 pmMontego Bay Sangster Intl

7h 09m

1 stop

MDW9:58 pmChicago Midway

$452

Frontier

Aug 2

MDW6:05 amChicago Midway

6h 19m

1 stop

MBJ12:24 pmMontego Bay Sangster Intl

Aug 5

MBJ1:32 pmMontego Bay Sangster Intl

8h 31m

1 stop

MDW10:03 pmChicago Midway

$472

Frontier

Jul 18

MDW6:05 amChicago Midway

6h 22m

1 stop

MBJ12:27 pmMontego Bay Sangster Intl

Aug 2

MBJ1:39 pmMontego Bay Sangster Intl

8h 24m

1 stop

MDW10:03 pmChicago Midway

$492

Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets

Southwest

Nov 1

MDW8:40 pmChicago Midway

16h 45m

2 stops

MBJ2:25 pmMontego Bay Sangster Intl

Nov 5

MBJ1:50 pmMontego Bay Sangster Intl

10h 05m

1 stop

MDW10:55 pmChicago Midway

$453

Southwest

Aug 16

MDW5:00 amChicago Midway

8h 30m

2 stops

MBJ1:30 pmMontego Bay Sangster Intl

Aug 21

MBJ2:15 pmMontego Bay Sangster Intl

7h 15m

1 stop

MDW9:30 pmChicago Midway

$473

Southwest

Nov 3

MDW8:10 amChicago Midway

5h 35m

1 stop

MBJ2:45 pmMontego Bay Sangster Intl

Nov 10

MBJ1:50 pmMontego Bay Sangster Intl

6h 45m

1 stop

MDW7:35 pmChicago Midway

$498

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

2:00 pm-11:44 pm

1 stop10h 44m

$384

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

Thu 11/5

2:00 pm-11:44 pm

1 stop10h 44m

$394

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 9/13

6:00 am-4:02 pm

1 stop10h 02m

Kingston Norman Manley

Thu 9/17

1:08 pm-11:32 pm

1 stop10h 24m

$398

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 9/13

5:00 am-4:02 pm

2 stops11h 02m

Kingston Norman Manley

Thu 9/17

1:08 pm-11:56 pm

2 stops10h 48m

$403

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

6:05 am-1:01 pm

1 stop6h 56m

Montego Bay Sangster Intl

Fri 8/21

1:09 pm-10:36 pm

1 stop9h 27m

$448

Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/19

7:25 am-1:31 pm

1 stop6h 06m

Montego Bay Sangster Intl

Sat 9/26

2:49 pm-9:58 pm

1 stop7h 09m

$452

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 8/21

12:46 pm-8:13 pm

1 stop7h 27m

Kingston Norman Manley

Sun 8/23

9:13 am-4:15 pm

1 stop7h 02m

$464

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/2

6:05 am-12:24 pm

1 stop6h 19m

Montego Bay Sangster Intl

Wed 8/5

1:32 pm-10:03 pm

1 stop8h 31m

$472

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

5:00 am-1:30 pm

2 stops8h 30m

Montego Bay Sangster Intl

Fri 8/21

2:15 pm-9:30 pm

1 stop7h 15m

$473

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

5:10 am-1:30 pm

1 stop8h 20m

Montego Bay Sangster Intl

Wed 8/19

12:55 pm-9:00 pm

1 stop8h 05m

$513

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 $492. 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 $622.

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 $523 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	$252
Fastest flight time	3h 50m
Direct flights	Every day
Airports in Jamaica	11 airports

The best one-way flight to Jamaica from Chicago in the past 72 hours is $252. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $540.

The fastest flight from Chicago to Jamaica takes 3h 50m

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 (75.93% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (14.44%), Boeing 737 (4.07%), and Airbus A321-100/200 (3.70%).

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 2,858 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.8 8,455 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 3,014 reviews	Search JetBlue flights
United Airlines	PriceFrom $297	Free Cancellation	Rating 7.4 9,900 reviews	Search United Airlines flights
American Airlines	PriceFrom $318	Free Cancellation	Rating 7.1 11,779 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 7.9 4,246 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

Find my bookings

Get notified when prices go down

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

1 adult

Tue 7/28

Tue 8/4

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Jamaica

Popular cities

Other flights from Chicago

Other flights to Jamaica

Airlines

Cabin classes

Complete your trip

Feeling lucky

Popular cities in Jamaica

Flights to Montego Bayfrom $324

Flights to Kingstonfrom $386

Flights to Ocho Rios

Cheap flights from Chicago to Jamaica from $160

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 9/21. 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

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Frontier flights from Chicago to Jamaica

Our best Frontier 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?

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

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