What airlines fly to Chicago?

American Airlines, United Airlines and Southwest 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 61% 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 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 26m on average, while flying from Kingston to Chicago O'Hare Intl Airport is 10h 05m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

JetBlue, Delta, and United Airlines are the most popular carriers operating from Jamaica to 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 September 2026.

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.

$199 Cheap Flights from Jamaica to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Jamaica to Chicago

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One-way

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Recent round-trip flight deals from Jamaica to Chicago

Enter your travel dates to find the best prices.

12:13 pm - 11:00 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

10h 47m1 stop Charlotte Douglas

6:55 am - 4:12 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

9h 17m1 stop Dallas/Fort Worth

$326American Airlines

Thu, Oct 22 - Sun, Oct 25

12:13 pm - 11:36 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

11h 23m2 stops Charlotte Douglas Washington, D.C. Reagan-National

6:00 am - 4:12 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

10h 12m1 stop Dallas/Fort Worth

$331American Airlines

Thu, Oct 22 - Sun, Oct 25

3:48 pm - 11:43 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

7h 55m1 stop Atlanta Hartsfield-Jackson

6:24 am - 2:33 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

8h 09m1 stop Atlanta Hartsfield-Jackson

$368Frontier

Thu, Oct 22 - Sun, Oct 25

12:30 pm - 9:00 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

20h 30m1 stop Toronto Pearson Intl

8:45 am - 4:20 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 35m1 stop Toronto Pearson Intl

$372Air Canada

Wed, Oct 21 - Mon, Oct 26

12:18 pm - 11:00 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

10h 42m1 stop Dallas/Fort Worth

9:40 am - 2:52 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 12mnonstop

$402American Airlines

Thu, Oct 29 - Tue, Nov 3

2:54 pm - 6:20 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 26mnonstop

8:40 am - 1:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$421United Airlines

Mon, Nov 23 - Sun, Nov 29

12:52 pm - 11:21 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

10h 29m1 stop Newark

8:40 am - 12:48 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

4h 08mnonstop

$422United Airlines

Thu, Oct 22 - Sun, Oct 25

12:00 pm - 6:35 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

6h 35m1 stop Orlando

5:00 am - 11:50 amMDW Chicago Midway-MBJ Montego Bay Sangster Intl

6h 50m1 stop Orlando

$490Southwest

Wed, Oct 21 - Mon, Oct 26

12:00 pm - 10:15 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

10h 15m2 stops Orlando Nashville Intl

5:00 am - 11:50 amMDW Chicago Midway-MBJ Montego Bay Sangster Intl

6h 50m1 stop Orlando

$511Southwest

Wed, Oct 21 - Mon, Oct 26

5:02 pm - 11:57 pmKIN Kingston Norman Manley-ORD Chicago O'Hare Intl

7h 55m1 stop Fort Lauderdale

7:00 am - 6:28 pmORD Chicago O'Hare Intl-KIN Kingston Norman Manley

10h 28m1 stop Fort Lauderdale

$1,452JetBlue

Sun, Nov 1 - Sun, Dec 13

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Air Canada flights from Jamaica to Chicago

Our best Air Canada deals on Jamaica to Chicago flight tickets

Air Canada

Oct 21

MBJ12:30 pmMontego Bay Sangster Intl

20h 30m

1 stop

ORD9:00 amChicago O'Hare Intl

Oct 26

ORD8:45 amChicago O'Hare Intl

7h 35m

1 stop

MBJ4:20 pmMontego Bay Sangster Intl

$372

Air Canada

Nov 23

MBJ6:20 pmMontego Bay Sangster Intl

16h 03m

1 stop

ORD9:23 amChicago O'Hare Intl

Nov 29

ORD4:30 pmChicago O'Hare Intl

23h 50m

1 stop

MBJ5:20 pmMontego Bay Sangster Intl

$373

Air Canada

Nov 23

MBJ6:20 pmMontego Bay Sangster Intl

17h 47m

2 stops

ORD11:07 amChicago O'Hare Intl

Nov 29

ORD4:30 pmChicago O'Hare Intl

23h 50m

1 stop

MBJ5:20 pmMontego Bay Sangster Intl

$376

United Airlines flights from Jamaica to Chicago

Our best United Airlines deals on Jamaica to Chicago flight tickets

United Airlines

Nov 23

MBJ2:54 pmMontego Bay Sangster Intl

4h 26m

ORD6:20 pmChicago O'Hare Intl

Nov 29

ORD8:40 amChicago O'Hare Intl

4h 08m

MBJ1:48 pmMontego Bay Sangster Intl

$421

United Airlines

Oct 22

MBJ12:52 pmMontego Bay Sangster Intl

10h 29m

1 stop

ORD11:21 pmChicago O'Hare Intl

Oct 25

ORD8:40 amChicago O'Hare Intl

4h 08m

MBJ12:48 pmMontego Bay Sangster Intl

$422

United Airlines

Nov 23

MBJ2:54 pmMontego Bay Sangster Intl

4h 26m

ORD6:20 pmChicago O'Hare Intl

Nov 28

ORD12:01 amChicago O'Hare Intl

13h 38m

1 stop

MBJ2:39 pmMontego Bay Sangster Intl

$426

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Thu 10/22

12:13 pm-11:00 pm

1 stop10h 47m

Chicago O'Hare Intl

Sun 10/25

6:55 am-4:12 pm

1 stop9h 17m

$326

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Thu 10/22

12:13 pm-11:36 pm

2 stops11h 23m

Chicago O'Hare Intl

Sun 10/25

6:00 am-4:12 pm

1 stop10h 12m

$331

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Thu 10/22

3:48 pm-11:43 pm

1 stop7h 55m

Chicago Midway

Sun 10/25

6:24 am-2:33 pm

1 stop8h 09m

$368

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 10/21

12:30 pm-9:00 am

1 stop20h 30m

Chicago O'Hare Intl

Mon 10/26

8:45 am-4:20 pm

1 stop7h 35m

$372

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Thu 10/29

12:18 pm-11:00 pm

1 stop10h 42m

Chicago O'Hare Intl

Tue 11/3

9:40 am-2:52 pm

Nonstop4h 12m

$402

Quickest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Mon 11/23

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Sun 11/29

8:40 am-1:48 pm

Nonstop4h 08m

$421

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Thu 10/22

12:52 pm-11:21 pm

1 stop10h 29m

Chicago O'Hare Intl

Sun 10/25

8:40 am-12:48 pm

Nonstop4h 08m

$422

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Wed 10/21

12:00 pm-6:35 pm

1 stop6h 35m

Chicago Midway

Mon 10/26

5:00 am-11:50 am

1 stop6h 50m

$490

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Wed 10/21

12:00 pm-10:15 pm

2 stops10h 15m

Chicago Midway

Mon 10/26

5:00 am-11:50 am

1 stop6h 50m

$511

KingstonChicago

KIN Kingston Norman Manley - ORD Chicago O'Hare Intl

KINORD

Kingston Norman Manley

Sun 11/1

5:02 pm-11:57 pm

1 stop7h 55m

Chicago O'Hare Intl

Sun 12/13

7:00 am-6:28 pm

1 stop10h 28m

$1,452

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 month to fly to Chicago?

The month of December is, on average, the cheapest month to fly to Chicago from Jamaica, with most prices found around $300. If you’re not able to fly to Chicago in December, then April is your next best option. Flight prices from Jamaica to Chicago during April average around $356.

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 $413. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Jamaica to Chicago for around $547.

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 $460.

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 2 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	$199
Fastest flight time	4h 10m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Jamaica in the past 72 hours is $199. The best round-trip flight deal from Jamaica to Chicago found on momondo in the last 72 hours is $326.

The fastest flight from Jamaica to Chicago takes 4h 10m

Direct flights go from Jamaica to Chicago every day.

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

Search flight deals

Frequently asked questions about flying from Jamaica to 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 September 2026.
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 (32.35% of total bookings). The next most popular plane models are Boeing 737-800 (10.29%), Boeing 737 (10.29%), and Airbus A321-100/200 (8.82%).

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
United Airlines	PriceFrom $281	Free Cancellation	Rating 7.4 10,209 reviews	Search United Airlines flights
Southwest	PriceFrom $281	Free Cancellation	Rating 8.0 4,190 reviews	Search Southwest flights
American Airlines	PriceFrom $281	Free Cancellation	Rating 7.1 12,060 reviews	Search American Airlines flights
JetBlue	PriceFrom $446	Free Cancellation	Rating 7.1 3,038 reviews	Search JetBlue flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

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 $199

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 11/13. 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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Air Canada flights from Jamaica to Chicago

Our best Air Canada deals on Jamaica to Chicago flight tickets

United Airlines flights from Jamaica to Chicago

Our best United Airlines deals on Jamaica to Chicago flight tickets

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How to get the cheapest flight ticket from Jamaica to Chicago

What is the cheapest month to fly 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?

What is the cheapest Jamaica to Chicago flight route?

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

Can stopping save me money on Jamaica to Chicago flights?

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

What airlines fly to Chicago?

How long does it take to fly to Chicago?

Cheap Jamaica to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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?

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.

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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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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