What is the cheapest airline that flies from Montego Bay Sangster Intl to Chicago?

JetBlue, United Airlines, and Delta are the most popular carriers operating from Montego Bay Sangster Intl to Chicago

What airlines fly to Chicago?

American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Chicago from Montego Bay according to our data. American Airlines is the first choice among our users, with 66% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Montego Bay Sangster Intl Airport to Chicago?

Prices for flights from Montego Bay Sangster Intl Airport to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Montego Bay Sangster Intl Airport to Chicago?

The number of operators available for flights from Montego Bay Sangster Intl Airport to Chicago is 2 as of September 2026.

How old do you have to be to fly from Montego Bay Sangster Intl Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Montego Bay Sangster Intl Airport to Chicago.

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

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$203 Cheap Flights from Montego Bay to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Montego Bay to Chicago

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Cheap round-trip flights

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4:23 pm - 11:47 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

8h 24m1 stop Atlanta Hartsfield-Jackson

6:16 am - 3:08 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

7h 52m1 stop Atlanta Hartsfield-Jackson

$360Frontier

Mon, Nov 2 - Mon, Nov 9

6:20 pm - 9:23 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

16h 03m1 stop Toronto Pearson Intl

4:30 pm - 5:20 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

23h 50m1 stop Toronto Pearson Intl

$369Air Canada

Mon, Nov 23 - Sun, Nov 29

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

$371Frontier

Sat, Oct 10 - Sun, Oct 18

6:20 pm - 9:23 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

16h 03m1 stop Toronto Pearson Intl

4:30 pm - 5:20 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

23h 50m1 stop Toronto Pearson Intl

$371Air Canada

Mon, Nov 23 - Sun, Nov 29

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

5:13 pm - 7:47 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

14h 34m1 stop Miami

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

4h 12mnonstop

$422American Airlines

Wed, Oct 21 - Tue, Nov 17

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

4h 26mnonstop

5:55 am - 2:14 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 19m1 stop Newark

$424United Airlines

Fri, Nov 6 - Sun, Nov 8

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

$424United Airlines

Fri, Nov 6 - Mon, Nov 9

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

10h 47m2 stops Charlotte Douglas New York LaGuardia

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

4h 12mnonstop

$426American Airlines

Wed, Oct 21 - Tue, Nov 17

3:49 pm - 7:45 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

4h 56mnonstop

8:47 pm - 12:45 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

14h 58m1 stop Philadelphia

$426American Airlines

Mon, Nov 23 - Sun, Nov 29

Cheap last minute flights

Enter your travel dates to find the best prices.

3:42 pm - 9:20 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

17h 38m1 stop Atlanta Hartsfield-Jackson

7:21 pm - 2:27 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

19h 06m1 stop Atlanta Hartsfield-Jackson

$412Frontier

Thu, Sep 24 - Sat, Sep 26

1:14 pm - 11:59 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

10h 45m1 stop Atlanta Hartsfield-Jackson

6:40 am - 1:01 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

6h 21m1 stop Atlanta Hartsfield-Jackson

$437Delta

Thu, Sep 24 - Mon, Sep 28

4:50 pm - 7:56 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

15h 06m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

5:30 am - 1:01 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 31m1 stop Atlanta Hartsfield-Jackson

$437Delta

Thu, Sep 24 - Mon, Sep 28

2:09 pm - 11:59 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 50m1 stop Charlotte Douglas

5:00 am - 4:16 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

11h 16m1 stop Dallas/Fort Worth

$446American Airlines

Fri, Sep 25 - Mon, Sep 28

5:16 pm - 7:58 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

14h 42m2 stops Miami Washington, D.C. Reagan-National

8:15 am - 4:16 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

8h 01m1 stop Dallas/Fort Worth

$451American Airlines

Thu, Sep 24 - Sat, Sep 26

5:16 pm - 7:58 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

14h 42m2 stops Miami Washington, D.C. Reagan-National

5:20 am - 12:53 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 33m2 stops Charlotte Douglas Miami

$451American Airlines

Thu, Sep 24 - Mon, Sep 28

1:54 pm - 11:36 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 42m2 stops Miami Washington, D.C. Reagan-National

5:00 am - 4:16 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

11h 16m1 stop Dallas/Fort Worth

$451American Airlines

Fri, Sep 25 - Mon, Sep 28

1:54 pm - 11:36 pmMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

9h 42m2 stops Miami Washington, D.C. Reagan-National

5:20 am - 12:53 pmORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

7h 33m2 stops Charlotte Douglas Miami

$451American Airlines

Fri, Sep 25 - Mon, Sep 28

12:30 pm - 7:44 amMBJ Montego Bay Sangster Intl-ORD Chicago O'Hare Intl

19h 14m2 stops Toronto Pearson Intl Ottawa

3:40 pm - 11:20 amORD Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl

19h 40m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$558Air Canada

Thu, Sep 24 - Sat, Sep 26

1:55 pm - 8:50 pmMBJ Montego Bay Sangster Intl-MDW Chicago Midway

6h 55m1 stop Baltimore/Washington

5:00 am - 1:05 pmMDW Chicago Midway-MBJ Montego Bay Sangster Intl

8h 05m1 stop Orlando

$886Southwest

Tue, Sep 29 - Sat, Oct 10

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Air Canada flights from Montego Bay to Chicago

Our best Air Canada deals on Montego Bay to Chicago flight tickets

Air Canada

Nov 5

MBJ1:50 pmMontego Bay Sangster Intl

20h 33m

1 stop

ORD9:23 amChicago O'Hare Intl

Nov 27

ORD12:50 pmChicago O'Hare Intl

27h 30m

1 stop

MBJ5:20 pmMontego Bay Sangster Intl

$334

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

$369

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

$371

JetBlue flights from Montego Bay to Chicago

Our best JetBlue deals on Montego Bay to Chicago flight tickets

JetBlue

Nov 2

MBJ4:02 pmMontego Bay Sangster Intl

8h 55m

1 stop

ORD11:57 pmChicago O'Hare Intl

Nov 9

ORD7:00 amChicago O'Hare Intl

6h 57m

1 stop

MBJ2:57 pmMontego Bay Sangster Intl

$387

JetBlue

Oct 21

MBJ12:03 pmMontego Bay Sangster Intl

11h 27m

1 stop

ORD11:30 pmChicago O'Hare Intl

Nov 11

ORD7:00 amChicago O'Hare Intl

6h 57m

1 stop

MBJ2:57 pmMontego Bay Sangster Intl

$409

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Mon 11/2

4:23 pm-11:47 pm

1 stop8h 24m

Chicago Midway

Mon 11/9

6:16 am-3:08 pm

1 stop7h 52m

$360

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Mon 11/23

6:20 pm-9:23 am

1 stop16h 03m

Chicago O'Hare Intl

Sun 11/29

4:30 pm-5:20 pm

1 stop23h 50m

$369

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Sat 10/10

3:48 pm-11:43 pm

1 stop7h 55m

Chicago Midway

Sun 10/18

6:24 am-2:33 pm

1 stop8h 09m

$371

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Mon 11/23

6:20 pm-9:23 am

1 stop16h 03m

Chicago O'Hare Intl

Sun 11/29

4:30 pm-5:20 pm

1 stop23h 50m

$371

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

Wed 10/21

5:13 pm-7:47 am

1 stop14h 34m

Chicago O'Hare Intl

Tue 11/17

9:40 am-2:52 pm

Nonstop4h 12m

$422

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Fri 11/6

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Sun 11/8

5:55 am-2:14 pm

1 stop7h 19m

$424

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Fri 11/6

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Mon 11/9

8:40 am-1:48 pm

Nonstop4h 08m

$424

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Wed 10/21

12:13 pm-11:00 pm

2 stops10h 47m

Chicago O'Hare Intl

Tue 11/17

9:40 am-2:52 pm

Nonstop4h 12m

$426

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Mon 11/23

3:49 pm-7:45 pm

Nonstop4h 56m

Chicago O'Hare Intl

Sun 11/29

8:47 pm-12:45 pm

1 stop14h 58m

$426

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 Montego Bay 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

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Montego Bay, with most prices found around $0. If you’re not able to fly to Chicago in January, then December is your next best option. Flight prices from Montego Bay to Chicago during December average around $300.

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 $402. 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 Montego Bay 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 at noon. Flights from Montego Bay to Chicago during this time can be as low as $457. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $486.

What is the cheapest Montego Bay Sangster Intl to Chicago flight route?

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

What cabin class options are available on Montego Bay to Chicago flights?

There are 2 cabin classes available to choose from on Montego Bay 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 Montego Bay to Chicago flights?

You could potentially save up to 12% on your flight if you consider stops on a Montego Bay to Chicago flight.

How have Montego Bay to Chicago flight prices changed over time?

As of September 2026, prices for Montego Bay to Chicago flights are approximately 14% more expensive when compared to flights at the same time last year.

When to book flights from Montego Bay to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Montego Bay to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Montego Bay to Chicago (MBJ to CHI) flight deals and tips

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

Best Price Found	$203
Fastest flight time	4h 10m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Montego Bay in the past 72 hours is $203. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $360.

The fastest flight from Montego Bay to Chicago takes 4h 10m

Direct flights go from Montego Bay to Chicago every day.

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

Search flight deals

Frequently asked questions about flying from Montego Bay to Chicago

How far is Montego Bay Sangster Intl to Chicago by plane?
The distance between Montego Bay Sangster Intl and Chicago is about 1713.9 mi. 4h 10m is a normal flight duration for this route.
When did momondo last update prices for flights from Montego Bay Sangster Intl Airport to Chicago?
Prices for flights from Montego Bay Sangster Intl Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Montego Bay Sangster Intl Airport to Chicago?
The number of operators available for flights from Montego Bay Sangster Intl Airport to Chicago is 2 as of September 2026.
How old do you have to be to fly from Montego Bay Sangster Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Montego Bay Sangster Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Montego Bay to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Montego Bay 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%).
What is the most popular airline from Montego Bay to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Montego Bay to Chicago is American Airlines (100% of total bookings).

Best airlines flying from Montego Bay to Chicago

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

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $281	Free Cancellation	Rating 7.4 10,226 reviews		Search United Airlines flights
American Airlines	PriceFrom $281	Free Cancellation	Rating 7.0 12,076 reviews		Search American Airlines flights

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Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Montego Bay to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from Montego Bay with this policy.

How can momondo help me find flights from Montego Bay to Chicago?

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 Montego Bay to Chicago.

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

If you are not ready to book a flight from Montego Bay to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Fly into one of these airports located in Chicago

Chicago Midway Airport

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Chicago Greater Rockford Airport

Cheap flights from Montego Bay to Chicago from $203

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montego Bay to Chicago departing on 11/20. 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 Montego Bay to Chicago

Our best Air Canada deals on Montego Bay to Chicago flight tickets

JetBlue flights from Montego Bay to Chicago

Our best JetBlue deals on Montego Bay to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Montego Bay 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 Montego Bay Sangster Intl to Chicago flight route?

What cabin class options are available on Montego Bay to Chicago flights?

Can stopping save me money on Montego Bay to Chicago flights?

How have Montego Bay to Chicago flight prices changed over time?

What is the cheapest airline that flies from Montego Bay Sangster Intl to Chicago?

What airlines fly to Chicago?

When to book flights from Montego Bay to Chicago

Cheap Montego Bay to Chicago (MBJ to CHI) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Montego Bay to Chicago

Best airlines flying from Montego Bay to Chicago

Compare and see reviews for airlines that fly from Montego Bay 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.

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

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.

Popular cities in the United States

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

Fly to other destinations from Montego Bay

According to popular flight searches on momondo this year

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