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

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from Jamaica to Chicago

What airlines fly to Chicago?

American Airlines, Spirit Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Jamaica according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

The number of flights available between Jamaica and Chicago is 6 per week as of December 2025. The most frequent departure day is Sat, with 33% of weekly flights leaving on this day.

How long does it take to fly to Chicago?

Average flight duration from Jamaica to Chicago depends on which airport you fly into and out of. Flying from Montego Bay to Chicago O'Hare Intl Airport is 4h 37m on average, while flying from Kingston to Chicago O'Hare Intl Airport is 6h 20m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

Prices for flights from Jamaica to Chicago refresh daily.

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

The number of operators available for flights from Jamaica to Chicago is 4 as of December 2025.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jamaica to Chicago.

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

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$150 Cheap Flights from Jamaica to Chicago in 2025/26

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Recent round-trip flight deals from Jamaica to Chicago

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12:57 pm - 9:03 pm

MBJ

ORD

9h 06m1 stop

5:15 am - 12:02 pm

ORD

MBJ

5h 47m1 stop

$232Spirit Airlines

Tue, Feb 10 - Sun, Feb 22

12:57 pm - 9:03 pm

MBJ

ORD

9h 06m1 stop

5:15 am - 12:02 pm

ORD

MBJ

5h 47m1 stop

$247Spirit Airlines

Mon, Feb 2 - Mon, Feb 9

12:57 pm - 10:46 pm

MBJ

ORD

10h 49m2 stops

8:43 pm - 12:02 pm

ORD

MBJ

14h 19m1 stop

$321Multiple Airlines

Mon, Feb 2 - Mon, Feb 9

12:57 pm - 9:03 pm

MBJ

ORD

9h 06m1 stop

1:17 pm - 12:02 pm

ORD

MBJ

21h 45m2 stops

$329Multiple Airlines

Tue, Feb 10 - Sun, Feb 22

4:27 pm - 9:53 am

MBJ

ORD

18h 26m1 stop

10:22 am - 3:28 pm

ORD

MBJ

4h 06mnonstop

$350American Airlines

Tue, Feb 10 - Sun, Feb 22

3:12 pm - 6:51 pm

MBJ

ORD

4h 39mnonstop

10:09 am - 3:22 pm

ORD

MBJ

4h 13mnonstop

$362American Airlines

Mon, Feb 2 - Mon, Feb 9

12:15 pm - 9:00 am

MBJ

ORD

20h 45m1 stop

8:20 pm - 11:20 am

ORD

MBJ

15h 00m1 stop

$384Air Canada

Mon, May 25 - Fri, Jun 5

9:00 am - 9:05 pm

KIN

ORD

13h 05m2 stops

9:55 am - 8:00 pm

ORD

KIN

9h 05m1 stop

$400Delta

Mon, Feb 2 - Mon, Feb 9

3:05 pm - 8:25 am

KIN

ORD

17h 20m2 stops

8:20 pm - 1:55 pm

ORD

KIN

17h 35m1 stop

$424Air Canada

Wed, May 13 - Tue, May 26

4:45 pm - 10:22 pm

MBJ

MDW

6h 37m1 stop

6:00 am - 12:53 pm

MDW

MBJ

5h 53m1 stop

$443Delta

Tue, Feb 10 - Sun, Feb 22

Spirit Airlines flights from Jamaica to Chicago

Our best Spirit Airlines deals on Jamaica to Chicago flight tickets

Spirit Airlines

Feb 10

MBJ12:57 pmMontego Bay Sangster Intl

9h 06m

1 stop

ORD9:03 pmChicago O'Hare Intl

Feb 22

ORD5:15 amChicago O'Hare Intl

5h 47m

1 stop

MBJ12:02 pmMontego Bay Sangster Intl

$232

Find similar

Spirit Airlines

Feb 2

MBJ12:57 pmMontego Bay Sangster Intl

9h 06m

1 stop

ORD9:03 pmChicago O'Hare Intl

Feb 9

ORD5:15 amChicago O'Hare Intl

5h 47m

1 stop

MBJ12:02 pmMontego Bay Sangster Intl

$247

Find similar

Spirit Airlines

Feb 2

KIN1:17 pmKingston Norman Manley

8h 46m

1 stop

ORD9:03 pmChicago O'Hare Intl

Feb 9

ORD5:15 amChicago O'Hare Intl

5h 57m

1 stop

KIN12:12 pmKingston Norman Manley

$303

Find similar

American Airlines flights from Jamaica to Chicago

Our best American Airlines deals on Jamaica to Chicago flight tickets

American Airlines

Feb 10

MBJ4:27 pmMontego Bay Sangster Intl

18h 26m

1 stop

ORD9:53 amChicago O'Hare Intl

Feb 22

ORD10:22 amChicago O'Hare Intl

4h 06m

MBJ3:28 pmMontego Bay Sangster Intl

$350

Find similar

American Airlines

Feb 2

MBJ3:12 pmMontego Bay Sangster Intl

4h 39m

ORD6:51 pmChicago O'Hare Intl

Feb 9

ORD10:09 amChicago O'Hare Intl

4h 13m

MBJ3:22 pmMontego Bay Sangster Intl

$362

Find similar

American Airlines

Feb 2

MBJ3:12 pmMontego Bay Sangster Intl

4h 39m

ORD6:51 pmChicago O'Hare Intl

Feb 9

ORD5:05 amChicago O'Hare Intl

9h 11m

1 stop

MBJ3:16 pmMontego Bay Sangster Intl

$367

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 2/10

12:57 pm-9:03 pm

1 stop9h 06m

Chicago O'Hare Intl

Sun 2/22

5:15 am-12:02 pm

1 stop5h 47m

$232

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 2/2

12:57 pm-9:03 pm

1 stop9h 06m

Chicago O'Hare Intl

Mon 2/9

5:15 am-12:02 pm

1 stop5h 47m

$247

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 2/2

12:57 pm-10:46 pm

2 stops10h 49m

Chicago O'Hare Intl

Mon 2/9

8:43 pm-12:02 pm

1 stop14h 19m

$321

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 2/10

12:57 pm-9:03 pm

1 stop9h 06m

Chicago O'Hare Intl

Sun 2/22

1:17 pm-12:02 pm

2 stops21h 45m

$329

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 2/10

4:27 pm-9:53 am

1 stop18h 26m

Chicago O'Hare Intl

Sun 2/22

10:22 am-3:28 pm

Nonstop4h 06m

$350

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 2/2

3:12 pm-6:51 pm

Nonstop4h 39m

Chicago O'Hare Intl

Mon 2/9

10:09 am-3:22 pm

Nonstop4h 13m

$362

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 5/25

12:15 pm-9:00 am

1 stop20h 45m

Chicago O'Hare Intl

Fri 6/5

8:20 pm-11:20 am

1 stop15h 00m

$384

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mon 2/2

9:00 am-9:05 pm

2 stops13h 05m

Chicago O'Hare Intl

Mon 2/9

9:55 am-8:00 pm

1 stop9h 05m

$400

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/13

3:05 pm-8:25 am

2 stops17h 20m

Chicago O'Hare Intl

Tue 5/26

8:20 pm-1:55 pm

1 stop17h 35m

$424

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 2/10

4:45 pm-10:22 pm

1 stop6h 37m

Chicago Midway

Sun 2/22

6:00 am-12:53 pm

1 stop5h 53m

$443

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 Jamaica to Chicago

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $436. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Jamaica to Chicago for around $557.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Jamaica to Chicago during this time can be as low as $454. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $502.

What is the cheapest Jamaica to Chicago flight route?

Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Jamaica - Chicago flight prices

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

There are 3 cabin classes available to choose from on Jamaica to Chicago 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 Jamaica to Chicago flights?

You could potentially save up to 10% on your flight if you consider stops on a Jamaica to Chicago flight.

Cheap Jamaica to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jamaica to Chicago

Best Price Found	$235
Fastest flight time	4h 37m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Jamaica in the past 72 hours is $235. The best round-trip flight deal from Jamaica to Chicago found on momondo in the last 72 hours is $433.

The fastest flight from Jamaica to Chicago takes 4h 37m

Direct flights go from Jamaica to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There are 3 airports in Chicago. From Jamaica there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Jamaica to Chicago?
Prices for flights from Jamaica to Chicago refresh daily.
How many operators does momondo search for flights from Jamaica to Chicago?
The number of operators available for flights from Jamaica to Chicago is 4 as of December 2025.
How old do you have to be to fly from Jamaica to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jamaica to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Jamaica to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Jamaica to Chicago is Boeing 737 MAX 8 (37.18% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (10.26%), Airbus A321-100/200 (7.69%), and Boeing 737-800 (7.69%).

Best airlines flying from Jamaica to Chicago

Compare and see reviews for airlines that fly from Jamaica to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $256	Free Cancellation	Rating 6.3 8,191 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $348	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights
United Airlines	PriceFrom $349	Free Cancellation	Rating 7.4 9,099 reviews	Search United Airlines flights
Southwest	PriceFrom $392	Free Cancellation	Rating 8.0 4,256 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Jamaica to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for Jamaica to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Jamaica to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Jamaica. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Jamaica to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Jamaica to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from Jamaica to Chicago from $152

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jamaica to Chicago departing on 2/10. 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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Filter for what you want

Filter for what you want

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Find the cheapest flights from Jamaica to Chicago

Recent round-trip flight deals from Jamaica to Chicago

Recent one-way flight deals from Jamaica to Chicago

Recent last minute flight deals from Jamaica to Chicago

Recent direct flight deals from Jamaica to Chicago

Spirit Airlines flights from Jamaica to Chicago

Our best Spirit Airlines deals on Jamaica to Chicago flight tickets

American Airlines flights from Jamaica to Chicago

Our best American Airlines deals on Jamaica to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Jamaica to Chicago

What is the cheapest day to depart on your flight to Chicago?

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Jamaica to Chicago during this time can be as low as $454. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $502.

What is the cheapest Jamaica to Chicago flight route?

Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Jamaica - Chicago flight prices

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

There are 3 cabin classes available to choose from on Jamaica to Chicago 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 Jamaica to Chicago flights?

You could potentially save up to 10% on your flight if you consider stops on a Jamaica to Chicago flight.

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

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from Jamaica to Chicago

What airlines fly to Chicago?

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

The number of flights available between Jamaica and Chicago is 6 per week as of December 2025. The most frequent departure day is Sat, with 33% of weekly flights leaving on this day.

How long does it take to fly to Chicago?

Cheap Jamaica to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jamaica to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

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

What is the most popular plane model from Jamaica to Chicago?

Best airlines flying from Jamaica to Chicago

Compare and see reviews for airlines that fly from Jamaica to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights from Jamaica to Chicago?

I’m not ready to book a flight from Jamaica to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago