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

Spirit Airlines, American Airlines, and Frontier 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 22m on average, while flying from Kingston to Chicago O'Hare Intl Airport is 9h 20m on average. Chicago O'Hare Intl Airport is the most popular airport in 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 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 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 14 per week as of August 2025. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

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

The number of flights available between Jamaica and Chicago is 2 per day as of August 2025. The most frequent departure time is 2:00PM, with 100% of daily flights leaving in the afternoon.

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 5 as of August 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.

$149 Cheap Flights from Jamaica to Chicago in 2025

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Find the cheapest flights from Jamaica to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Jamaica to Chicago

12:10 pm - 10:48 pmMBJ-ORD

10h 38m1 stop

5:05 am - 11:05 amORD-MBJ

6h 00m1 stop

$210Spirit Airlines

Find Deal

Wed, Sep 10 - Tue, Sep 16

12:10 pm - 10:48 pmMBJ-ORD

10h 38m1 stop

5:05 am - 11:05 amORD-MBJ

6h 00m1 stop

$239Spirit Airlines

Find Deal

Wed, Sep 10 - Tue, Sep 30

2:00 pm - 6:30 pmMBJ-ORD

4h 30mnonstop

8:30 am - 12:31 pmORD-MBJ

4h 01mnonstop

$334American Airlines

Find Deal

Thu, Aug 28 - Mon, Sep 1

2:00 pm - 6:30 pmMBJ-ORD

4h 30mnonstop

5:00 am - 1:49 pmORD-MBJ

8h 49m1 stop

$338American Airlines

Find Deal

Thu, Aug 28 - Mon, Sep 1

1:20 pm - 9:26 pmMBJ-MDW

8h 06m1 stop

6:00 am - 12:00 pmMDW-MBJ

6h 00m1 stop

$339Delta

Find Deal

Wed, Sep 10 - Tue, Sep 30

9:58 am - 11:08 pmMBJ-MDW

13h 10m1 stop

6:15 am - 12:45 pmMDW-MBJ

6h 30m1 stop

$366Frontier

Find Deal

Sat, Aug 30 - Sat, Sep 13

2:05 pm - 11:17 pmMBJ-MDW

9h 12m1 stop

9:00 am - 12:45 pmMDW-MBJ

27h 45m1 stop

$370Frontier

Find Deal

Sat, Sep 20 - Wed, Oct 1

3:00 pm - 10:25 pmMBJ-MDW

7h 25m1 stop

6:35 am - 2:00 pmMDW-MBJ

7h 25m1 stop

$413Southwest

Find Deal

Thu, Aug 28 - Mon, Sep 1

9:00 am - 4:18 pmKIN-ORD

8h 18m1 stop

7:00 am - 8:00 pmORD-KIN

12h 00m2 stops

$456Delta

Find Deal

Sat, Dec 27 - Sat, Jan 3

3:00 pm - 10:25 pmMBJ-MDW

7h 25m1 stop

5:40 am - 2:00 pmMDW-MBJ

8h 20m2 stops

$513Southwest

Find Deal

Thu, Aug 28 - Mon, Sep 1

Spirit Airlines flights from Jamaica to Chicago

Our best Spirit Airlines deals on Jamaica to Chicago flight tickets

Spirit Airlines

Sep 10

MBJ12:10 pmMontego Bay Sangster Intl

10h 38m

1 stop

ORD10:48 pmChicago O'Hare Intl

Sep 16

ORD5:05 amChicago O'Hare Intl

6h 00m

1 stop

MBJ11:05 amMontego Bay Sangster Intl

$210

Find similar

Spirit Airlines

Sep 10

MBJ12:10 pmMontego Bay Sangster Intl

10h 38m

1 stop

ORD10:48 pmChicago O'Hare Intl

Sep 30

ORD5:05 amChicago O'Hare Intl

6h 00m

1 stop

MBJ11:05 amMontego Bay Sangster Intl

$239

Find similar

Spirit Airlines

Aug 28

MBJ12:19 pmMontego Bay Sangster Intl

11h 40m

1 stop

ORD11:59 pmChicago O'Hare Intl

Sep 1

ORD5:05 amChicago O'Hare Intl

6h 09m

1 stop

MBJ11:14 amMontego Bay Sangster Intl

$260

Find similar

American Airlines flights from Jamaica to Chicago

Our best American Airlines deals on Jamaica to Chicago flight tickets

American Airlines

Aug 28

MBJ2:00 pmMontego Bay Sangster Intl

4h 30m

ORD6:30 pmChicago O'Hare Intl

Sep 1

ORD8:30 amChicago O'Hare Intl

4h 01m

MBJ12:31 pmMontego Bay Sangster Intl

$334

Find similar

American Airlines

Aug 28

MBJ2:00 pmMontego Bay Sangster Intl

4h 30m

ORD6:30 pmChicago O'Hare Intl

Sep 1

ORD5:00 amChicago O'Hare Intl

8h 49m

1 stop

MBJ1:49 pmMontego Bay Sangster Intl

$338

Find similar

American Airlines

Sep 10

MBJ1:55 pmMontego Bay Sangster Intl

9h 53m

2 stops

ORD11:48 pmChicago O'Hare Intl

Sep 30

ORD5:00 amChicago O'Hare Intl

8h 38m

1 stop

MBJ1:38 pmMontego Bay Sangster Intl

$353

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/10

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 9/16

5:05 am-11:05 am

1 stop6h 00m

$210

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/10

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 9/30

5:05 am-11:05 am

1 stop6h 00m

$239

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/28

2:00 pm-6:30 pm

Nonstop4h 30m

Chicago O'Hare Intl

Mon 9/1

8:30 am-12:31 pm

Nonstop4h 01m

$334

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 8/28

2:00 pm-6:30 pm

Nonstop4h 30m

Chicago O'Hare Intl

Mon 9/1

5:00 am-1:49 pm

1 stop8h 49m

$338

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 9/10

1:20 pm-9:26 pm

1 stop8h 06m

Chicago Midway

Tue 9/30

6:00 am-12:00 pm

1 stop6h 00m

$339

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 8/30

9:58 am-11:08 pm

1 stop13h 10m

Chicago Midway

Sat 9/13

6:15 am-12:45 pm

1 stop6h 30m

$366

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 9/20

2:05 pm-11:17 pm

1 stop9h 12m

Chicago Midway

Wed 10/1

9:00 am-12:45 pm

1 stop27h 45m

$370

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 8/28

3:00 pm-10:25 pm

1 stop7h 25m

Chicago Midway

Mon 9/1

6:35 am-2:00 pm

1 stop7h 25m

$413

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Sat 12/27

9:00 am-4:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Sat 1/3

7:00 am-8:00 pm

2 stops12h 00m

$456

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 8/28

3:00 pm-10:25 pm

1 stop7h 25m

Chicago Midway

Mon 9/1

5:40 am-2:00 pm

2 stops8h 20m

$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 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 September is, on average, the cheapest month to fly to Chicago from Jamaica, with most prices found around $351. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Jamaica to Chicago during August average around $400.

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 $440. 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 $634.

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 $489. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $507.

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 4 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.

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	$149
Fastest flight time	4h 28m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Jamaica in the past 72 hours is $149. The best round-trip flight deal from Jamaica to Chicago found on momondo in the last 72 hours is $210.

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

Direct flights go from Jamaica to Chicago every day.

There are 2 airports near Chicago: 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 5 as of August 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 (28.74% of total bookings). The next most popular plane models are Boeing 737-800 (Scimitar Winglets) (20.36%), Airbus A321neo (16.17%), and Airbus A321-100/200 (8.38%).

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 $251	Free Cancellation	Rating 6.3 8,045 reviews	Search Spirit Airlines flights
Delta	PriceFrom $322	Free Cancellation	Rating 8.0 7,980 reviews	Search Delta flights
United Airlines	PriceFrom $383	Free Cancellation	Rating 7.4 8,916 reviews	Search United Airlines flights
Southwest	PriceFrom $392	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights
American Airlines	PriceFrom $402	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

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 $149

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 9/17. 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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Use the filters below to find and compare flights from Jamaica to Chicago that are best for you.

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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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Jamaica, with most prices found around $351. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Jamaica to Chicago during August average around $400.

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 $489. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $507.

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 4 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.

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

Spirit Airlines, American Airlines, and Frontier 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 day?

The number of flights available between Jamaica and Chicago is 2 per day as of August 2025. 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 14 per week as of August 2025. The most frequent departure day is Mon, with 14% 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