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

Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from Chicago to Jamaica

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

1 flights are operational daily from Chicago to Jamaica as of December 2025. The most popular departure time for this route is 10:00AM, with 100% of flights per day taking off at noon.

What airlines fly to Jamaica?

American Airlines, United Airlines and Spirit Airlines 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.

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

As of December 2025, there are 7 flights per week flying from Chicago to Jamaica. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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 December 2025, 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.

$106 Cheap Flights from Chicago to Jamaica in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:11 am - 3:51 pm

ORD

MBJ

8h 40m1 stop

3:49 pm - 10:24 pm

MBJ

ORD

7h 35m1 stop

$353Frontier

Sat, Dec 13 - Wed, Dec 24

6:11 am - 3:51 pm

ORD

MBJ

8h 40m1 stop

3:34 pm - 10:46 pm

MBJ

ORD

8h 12m1 stop

$354Frontier

Sat, Dec 13 - Sat, Dec 27

5:15 am - 12:02 pm

ORD

MBJ

5h 47m1 stop

1:00 pm - 7:29 pm

MBJ

ORD

7h 29m1 stop

$355Multiple Airlines

Fri, Jan 30 - Thu, Feb 12

7:59 pm - 12:02 pm

ORD

MBJ

15h 03m1 stop

1:00 pm - 12:18 am

MBJ

ORD

12h 18m1 stop

$356Spirit Airlines

Mon, Feb 23 - Sat, Feb 28

5:15 am - 12:02 pm

ORD

MBJ

5h 47m1 stop

12:57 pm - 7:38 pm

MBJ

ORD

7h 41m1 stop

$359Spirit Airlines

Fri, Jan 9 - Thu, Jan 22

8:56 pm - 12:02 pm

MDW

MBJ

14h 06m2 stops

4:51 pm - 11:25 pm

MBJ

MDW

7h 34m1 stop

$380Multiple Airlines

Mon, Feb 23 - Sat, Feb 28

5:31 pm - 11:13 am

MDW

MBJ

16h 42m1 stop

2:19 pm - 10:22 pm

MBJ

MDW

9h 03m1 stop

$391Delta

Tue, Jan 6 - Wed, Jan 28

6:45 am - 8:00 pm

MDW

KIN

12h 15m1 stop

9:00 am - 5:29 pm

KIN

MDW

9h 29m1 stop

$445Delta

Wed, Jan 7 - Tue, Jan 27

7:56 pm - 10:17 am

ORD

KIN

13h 21m2 stops

3:22 pm - 8:48 am

KIN

ORD

18h 26m1 stop

$460American Airlines

Wed, Feb 11 - Tue, Feb 17

7:30 pm - 12:47 pm

ORD

KIN

16h 17m1 stop

7:00 am - 11:08 pm

KIN

ORD

17h 08m1 stop

$485American Airlines

Fri, Jan 16 - Tue, Jan 20

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets

Frontier

Dec 13

ORD6:11 amChicago O'Hare Intl

8h 40m

1 stop

MBJ3:51 pmMontego Bay Sangster Intl

Dec 24

MBJ3:49 pmMontego Bay Sangster Intl

7h 35m

1 stop

ORD10:24 pmChicago O'Hare Intl

$353

Find similar

Frontier

Dec 13

ORD6:11 amChicago O'Hare Intl

8h 40m

1 stop

MBJ3:51 pmMontego Bay Sangster Intl

Dec 26

MBJ10:14 amMontego Bay Sangster Intl

9h 19m

1 stop

ORD6:33 pmChicago O'Hare Intl

$354

Find similar

Frontier

Feb 21

MDW6:00 amChicago Midway

8h 31m

1 stop

MBJ3:31 pmMontego Bay Sangster Intl

Feb 28

MBJ4:51 pmMontego Bay Sangster Intl

7h 34m

1 stop

MDW11:25 pmChicago Midway

$362

Find similar

American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets

American Airlines

Feb 17

ORD10:22 amChicago O'Hare Intl

4h 06m

MBJ3:28 pmMontego Bay Sangster Intl

Feb 25

MBJ4:38 pmMontego Bay Sangster Intl

4h 37m

ORD8:15 pmChicago O'Hare Intl

$377

Find similar

American Airlines

Feb 17

ORD6:10 amChicago O'Hare Intl

7h 49m

1 stop

MBJ2:59 pmMontego Bay Sangster Intl

Feb 25

MBJ4:38 pmMontego Bay Sangster Intl

4h 37m

ORD8:15 pmChicago O'Hare Intl

$381

Find similar

American Airlines

Jan 5

ORD10:11 amChicago O'Hare Intl

4h 13m

MBJ3:24 pmMontego Bay Sangster Intl

Jan 14

MBJ4:27 pmMontego Bay Sangster Intl

17h 11m

1 stop

ORD8:38 amChicago O'Hare Intl

$387

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 12/13

6:11 am-3:51 pm

1 stop8h 40m

Montego Bay Sangster Intl

Wed 12/24

3:49 pm-10:24 pm

1 stop7h 35m

$353

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 12/13

6:11 am-3:51 pm

1 stop8h 40m

Montego Bay Sangster Intl

Sat 12/27

3:34 pm-10:46 pm

1 stop8h 12m

$354

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/30

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Thu 2/12

1:00 pm-7:29 pm

1 stop7h 29m

$355

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/23

7:59 pm-12:02 pm

1 stop15h 03m

Montego Bay Sangster Intl

Sat 2/28

1:00 pm-12:18 am

1 stop12h 18m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/9

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Thu 1/22

12:57 pm-7:38 pm

1 stop7h 41m

$359

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/23

8:56 pm-12:02 pm

2 stops14h 06m

Montego Bay Sangster Intl

Sat 2/28

4:51 pm-11:25 pm

1 stop7h 34m

$380

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/6

5:31 pm-11:13 am

1 stop16h 42m

Montego Bay Sangster Intl

Wed 1/28

2:19 pm-10:22 pm

1 stop9h 03m

$391

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 1/7

6:45 am-8:00 pm

1 stop12h 15m

Kingston Norman Manley

Tue 1/27

9:00 am-5:29 pm

1 stop9h 29m

$445

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 2/11

7:56 pm-10:17 am

2 stops13h 21m

Kingston Norman Manley

Tue 2/17

3:22 pm-8:48 am

1 stop18h 26m

$460

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 1/16

7:30 pm-12:47 pm

1 stop16h 17m

Kingston Norman Manley

Tue 1/20

7:00 am-11:08 pm

1 stop17h 08m

$485

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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 January. Flight prices, which tend to average around $532, 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 January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $540.

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 $546. 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 $683.

What is the cheapest time of day to depart on your flight to Jamaica?

Our most recent data shows that the best time of day to fly to Jamaica is at noon. Flights from Chicago to Jamaica during this time can be as low as $287. In the morning is when there is more demand to fly to Jamaica, so prices are often more expensive at around $603 per ticket.

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 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 $583 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 $554 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?

You could potentially save up to 3% 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	$215
Fastest flight time	3h 50m
Direct flights	Every day
Airports in Jamaica	1 airport

The best one-way flight to Jamaica from Chicago in the past 72 hours is $215. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $477.

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

Direct flights go from Chicago to Jamaica every day.

There is 1 airport near Jamaica: Montego Bay Sangster Intl (MBJ)

Search flight deals

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 December 2025, 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 (56.73% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (36.22%), Airbus A321-100/200 (5.20%), and Boeing 737-900 (0.61%).

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
Spirit Airlines	PriceFrom $174	Free Cancellation	Rating 6.3 8,166 reviews	Search Spirit Airlines flights
Delta	PriceFrom $186	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
United Airlines	PriceFrom $356	Free Cancellation	Rating 7.4 9,078 reviews	Search United Airlines flights
Frontier	PriceFrom $370	Free Cancellation	Rating 5.8 3,087 reviews	Search Frontier flights
American Airlines	PriceFrom $433	Free Cancellation	Rating 7.2 11,044 reviews	Search American Airlines flights
Southwest	PriceFrom $549	Free Cancellation	Rating 8.0 4,252 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

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Find better results for your trip to Jamaica

Popular cities in Jamaica

Flights to Montego Bayfrom $221

Flights to Kingstonfrom $252

Flights to Ocho Rios

Cheap flights from Chicago to Jamaica from $106

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 2/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

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Trusted and free

Price Alerts

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Find the cheapest flights from Chicago to Jamaica

Cheap round-trip flights

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Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets

American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets

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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

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

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 time of day to depart on your flight to Jamaica?

Our most recent data shows that the best time of day to fly to Jamaica is at noon. Flights from Chicago to Jamaica during this time can be as low as $287. In the morning is when there is more demand to fly to Jamaica, so prices are often more expensive at around $603 per ticket.

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 to Jamaica?

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?

You could potentially save up to 3% on your flight if you consider stops on a Chicago to Jamaica flight.

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

Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from Chicago to Jamaica

What airlines fly to Jamaica?

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

1 flights are operational daily from Chicago to Jamaica as of December 2025. The most popular departure time for this route is 10:00AM, with 100% of flights per day taking off at noon.

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

As of December 2025, there are 7 flights per week flying from Chicago to Jamaica. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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

When did momondo last update prices for flights from Chicago to Jamaica?

How many operators does momondo search for flights from Chicago to Jamaica?

How old do you have to be to fly from Chicago to Jamaica?

What documentation or ID do you need to fly to Jamaica?

What is the most popular plane model 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?

Why should I use momondo to find a flight deal from Chicago to Jamaica?

Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?

How can momondo help me find flights 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?

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