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

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

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 28m on average, while flying from Kingston to Chicago O'Hare Intl Airport is 7h 39m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

The number of flights available between Jamaica and Chicago is 1 per day as of June 2026. The most frequent departure time is 2:00PM, with 100% of daily flights leaving in the afternoon.

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

The number of flights available between Jamaica and Chicago is 7 per week as of June 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

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 2 as of June 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.

$183 Cheap Flights from Jamaica to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Jamaica to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Jamaica to Chicago

Enter your travel dates to find the best prices.

4:33 pm - 9:05 am

MBJ

ORD

16h 32m

1 stop

11:15 am - 3:10 pm

ORD

MBJ

27h 55m

1 stop

$321United Airlines

Sat, Jul 4 - Sat, Jul 11

4:12 pm - 11:31 pm

MBJ

ORD

7h 19m

1 stop

6:29 am - 3:26 pm

ORD

MBJ

8h 57m

1 stop

$326United Airlines

Fri, Jul 17 - Sun, Jul 19

3:59 pm - 11:44 pm

MBJ

ORD

8h 45m

1 stop

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

$334JetBlue

Thu, Nov 12 - Mon, Nov 16

4:12 pm - 11:40 pm

MBJ

ORD

7h 28m

1 stop

8:45 am - 3:10 pm

ORD

MBJ

6h 25m

1 stop

$347United Airlines

Thu, Aug 13 - Mon, Aug 17

2:12 pm - 6:55 pm

MBJ

ORD

4h 43mnonstop

9:00 am - 1:12 pm

ORD

MBJ

4h 12mnonstop

$396American Airlines

Thu, Aug 13 - Mon, Aug 17

2:12 pm - 6:55 pm

MBJ

ORD

4h 43mnonstop

7:30 am - 1:28 pm

ORD

MBJ

5h 58m

1 stop

$401American Airlines

Thu, Aug 13 - Mon, Aug 17

4:59 pm - 7:56 am

MBJ

ORD

14h 57m

2 stops

6:40 am - 3:34 pm

ORD

MBJ

8h 54m

1 stop

$412Delta

Thu, Aug 13 - Mon, Aug 17

1:26 pm - 10:11 pm

MBJ

MDW

8h 45m

1 stop

6:00 am - 12:21 pm

MDW

MBJ

6h 21m

1 stop

$435Frontier

Sat, Jul 4 - Tue, Sep 1

1:26 pm - 10:11 pm

MBJ

MDW

8h 45m

1 stop

6:05 am - 12:27 pm

MDW

MBJ

6h 22m

1 stop

$455Frontier

Sat, Jul 4 - Sat, Jul 11

6:00 am - 1:39 pm

KIN

ORD

7h 39m

1 stop

6:27 pm - 8:14 pm

ORD

KIN

25h 47m

1 stop

$460JetBlue

Tue, Sep 1 - Tue, Sep 1

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United Airlines flights from Jamaica to Chicago

Our best United Airlines deals on Jamaica to Chicago flight tickets

United Airlines

Jul 4

MBJ4:33 pmMontego Bay Sangster Intl

16h 32m

1 stop

ORD9:05 amChicago O'Hare Intl

Jul 11

ORD11:15 amChicago O'Hare Intl

27h 55m

1 stop

MBJ3:10 pmMontego Bay Sangster Intl

$321

United Airlines

Jul 17

MBJ4:12 pmMontego Bay Sangster Intl

7h 19m

1 stop

ORD11:31 pmChicago O'Hare Intl

Jul 19

ORD6:29 amChicago O'Hare Intl

8h 57m

1 stop

MBJ3:26 pmMontego Bay Sangster Intl

$326

United Airlines

Aug 13

MBJ4:12 pmMontego Bay Sangster Intl

7h 28m

1 stop

ORD11:40 pmChicago O'Hare Intl

Aug 17

ORD8:45 amChicago O'Hare Intl

6h 25m

1 stop

MBJ3:10 pmMontego Bay Sangster Intl

$347

Air Canada flights from Jamaica to Chicago

Our best Air Canada deals on Jamaica to Chicago flight tickets

Air Canada

Jun 12

KIN3:05 pmKingston Norman Manley

17h 55m

1 stop

ORD9:00 amChicago O'Hare Intl

Jun 14

ORD6:22 pmChicago O'Hare Intl

19h 33m

2 stops

KIN1:55 pmKingston Norman Manley

$483

Air Canada

Jun 12

KIN3:05 pmKingston Norman Manley

19h 13m

2 stops

ORD10:18 amChicago O'Hare Intl

Jun 14

ORD6:22 pmChicago O'Hare Intl

19h 33m

2 stops

KIN1:55 pmKingston Norman Manley

$487

Air Canada

Jun 12

MBJ12:30 pmMontego Bay Sangster Intl

21h 15m

1 stop

ORD9:45 amChicago O'Hare Intl

Jun 14

ORD6:22 pmChicago O'Hare Intl

16h 58m

2 stops

MBJ11:20 amMontego Bay Sangster Intl

$490

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 7/4

4:33 pm-9:05 am

1 stop16h 32m

Chicago O'Hare Intl

Sat 7/11

11:15 am-3:10 pm

1 stop27h 55m

$321

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 7/17

4:12 pm-11:31 pm

1 stop7h 19m

Chicago O'Hare Intl

Sun 7/19

6:29 am-3:26 pm

1 stop8h 57m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/12

3:59 pm-11:44 pm

1 stop8h 45m

Chicago O'Hare Intl

Mon 11/16

7:00 am-2:54 pm

1 stop6h 54m

$334

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

4:12 pm-11:40 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 8/17

8:45 am-3:10 pm

1 stop6h 25m

$347

Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Mon 8/17

9:00 am-1:12 pm

Nonstop4h 12m

$396

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Mon 8/17

7:30 am-1:28 pm

1 stop5h 58m

$401

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/13

4:59 pm-7:56 am

2 stops14h 57m

Chicago O'Hare Intl

Mon 8/17

6:40 am-3:34 pm

1 stop8h 54m

$412

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Tue 9/1

6:00 am-12:21 pm

1 stop6h 21m

$435

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sat 7/11

6:05 am-12:27 pm

1 stop6h 22m

$455

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Tue 9/1

6:00 am-1:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Tue 9/1

6:27 pm-8:14 pm

1 stop25h 47m

$460

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 April is, on average, the cheapest month to fly to Chicago from Jamaica, with most prices found around $146. If you’re not able to fly to Chicago in April, then May is your next best option. Flight prices from Jamaica to Chicago during May average around $204.

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 Thursday when prices can be found for as low as $395. 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 $543.

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 $457.

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 5% 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	$289
Fastest flight time	4h 28m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Jamaica in the past 72 hours is $289. The best round-trip flight deal from Jamaica to Chicago found on momondo in the last 72 hours is $422.

The fastest flight from Jamaica to Chicago takes 4h 28m

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 2 as of June 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 737-800 (21.79% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (17.95%), Airbus A321-100/200 (17.95%), and Boeing 737-800 Passenger/BBJ2 (winglets) (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
United Airlines	PriceFrom $280	Free Cancellation	Rating 7.4 9,805 reviews		Search United Airlines flights
American Airlines	PriceFrom $281	Free Cancellation	Rating 7.1 11,640 reviews		Search American Airlines flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Saint Joseph

Lansing

Valparaiso

Schererville

Munster

Crown Point

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 $183

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 12/4. 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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United Airlines flights from Jamaica to Chicago

Our best United Airlines deals on Jamaica to Chicago flight tickets

Air Canada flights from Jamaica to Chicago

Our best Air Canada 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?

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

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

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

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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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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