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

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

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

1 flights are operational daily from Montego Bay to Chicago as of April 2026. The most popular departure time for this route is 1:00PM, with 100% of flights per day taking off in the afternoon.

What airlines fly to Chicago?

American Airlines, United Airlines and Spirit Airlines 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 64% 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 Montego Bay to Chicago on average per week?

The number of flights available between Montego Bay and Chicago is 11 per week as of April 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

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 3 as of April 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.

$170 Cheap Flights from Montego Bay to Chicago in 2026

Q: What is the typical price of a round-trip flight between Montego Bay and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $487 to $456. The lowest price recently found on this route was $281.

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0 bags

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Find the cheapest flights from Montego Bay to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

9:10 am - 1:17 pm

ORD

MBJ

4h 07mnonstop

$281American Airlines

Thu, May 14 - Mon, Aug 31

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

7:00 pm - 11:42 am

ORD

MBJ

16h 42m

1 stop

$286American Airlines

Thu, May 14 - Mon, Aug 31

4:12 pm - 7:27 am

MBJ

ORD

15h 15m

1 stop

6:30 am - 3:10 pm

ORD

MBJ

8h 40m

1 stop

$289United Airlines

Tue, Jun 2 - Fri, Jun 5

2:40 pm - 1:26 am

MBJ

ORD

10h 46m

1 stop

7:45 pm - 11:43 am

ORD

MBJ

15h 58m

1 stop

$290United Airlines

Wed, May 20 - Mon, Sep 14

2:40 pm - 7:53 am

MBJ

ORD

17h 13m

1 stop

9:56 pm - 1:30 pm

ORD

MBJ

15h 34m

1 stop

$291United Airlines

Sat, May 16 - Mon, May 18

1:16 pm - 10:02 pm

MBJ

MDW

8h 46m

1 stop

6:00 am - 12:11 pm

MDW

MBJ

6h 11m

1 stop

$334Frontier

Wed, May 20 - Tue, May 26

1:26 pm - 10:11 pm

MBJ

MDW

8h 45m

1 stop

6:00 am - 12:21 pm

MDW

MBJ

6h 21m

1 stop

$354Frontier

Wed, Jun 17 - Sun, Jun 21

11:35 am - 3:45 pm

MBJ

MDW

4h 10mnonstop

9:55 am - 1:45 pm

MDW

MBJ

3h 50mnonstop

$399Southwest

Sat, May 23 - Sat, May 30

4:59 pm - 12:42 pm

MBJ

MDW

19h 43m

2 stops

6:00 am - 3:34 pm

MDW

MBJ

9h 34m

1 stop

$411Delta

Thu, May 14 - Sat, Aug 29

11:35 am - 3:45 pm

MBJ

MDW

4h 10mnonstop

6:10 am - 1:30 pm

MDW

MBJ

7h 20m

1 stop

$449Southwest

Sat, May 23 - Sat, May 30

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American Airlines flights from Montego Bay to Chicago

Our best American Airlines deals on Montego Bay to Chicago flight tickets

American Airlines

May 14

MBJ1:15 pmMontego Bay Sangster Intl

4h 40m

ORD5:55 pmChicago O'Hare Intl

Aug 31

ORD9:10 amChicago O'Hare Intl

4h 07m

MBJ1:17 pmMontego Bay Sangster Intl

$281

American Airlines

May 14

MBJ1:15 pmMontego Bay Sangster Intl

4h 40m

ORD5:55 pmChicago O'Hare Intl

Aug 29

ORD8:20 amChicago O'Hare Intl

7h 53m

1 stop

MBJ4:13 pmMontego Bay Sangster Intl

$286

American Airlines

May 2

MBJ10:13 amMontego Bay Sangster Intl

9h 09m

1 stop

ORD7:22 pmChicago O'Hare Intl

May 4

ORD8:05 amChicago O'Hare Intl

4h 08m

MBJ12:13 pmMontego Bay Sangster Intl

$292

United Airlines flights from Montego Bay to Chicago

Our best United Airlines deals on Montego Bay to Chicago flight tickets

United Airlines

May 2

MBJ1:52 pmMontego Bay Sangster Intl

4h 23m

ORD6:15 pmChicago O'Hare Intl

May 4

ORD8:10 pmChicago O'Hare Intl

17h 20m

1 stop

MBJ1:30 pmMontego Bay Sangster Intl

$283

United Airlines

Jun 2

MBJ4:12 pmMontego Bay Sangster Intl

15h 15m

1 stop

ORD7:27 amChicago O'Hare Intl

Jun 5

ORD6:30 amChicago O'Hare Intl

8h 40m

1 stop

MBJ3:10 pmMontego Bay Sangster Intl

$289

United Airlines

May 20

MBJ2:40 pmMontego Bay Sangster Intl

10h 46m

1 stop

ORD1:26 amChicago O'Hare Intl

Sep 14

ORD7:45 pmChicago O'Hare Intl

15h 58m

1 stop

MBJ11:43 amMontego Bay Sangster Intl

$290

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Mon 8/31

9:10 am-1:17 pm

Nonstop4h 07m

$281

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Mon 8/31

7:00 pm-11:42 am

1 stop16h 42m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/2

4:12 pm-7:27 am

1 stop15h 15m

Chicago O'Hare Intl

Fri 6/5

6:30 am-3:10 pm

1 stop8h 40m

$289

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 5/20

2:40 pm-1:26 am

1 stop10h 46m

Chicago O'Hare Intl

Mon 9/14

7:45 pm-11:43 am

1 stop15h 58m

$290

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

2:40 pm-7:53 am

1 stop17h 13m

Chicago O'Hare Intl

Mon 5/18

9:56 pm-1:30 pm

1 stop15h 34m

$291

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 5/20

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Tue 5/26

6:00 am-12:11 pm

1 stop6h 11m

$334

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/17

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sun 6/21

6:00 am-12:21 pm

1 stop6h 21m

$354

Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/23

11:35 am-3:45 pm

Nonstop4h 10m

Chicago Midway

Sat 5/30

9:55 am-1:45 pm

Nonstop3h 50m

$399

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 5/14

4:59 pm-12:42 pm

2 stops19h 43m

Chicago Midway

Sat 8/29

6:00 am-3:34 pm

1 stop9h 34m

$411

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 5/23

11:35 am-3:45 pm

Nonstop4h 10m

Chicago Midway

Sat 5/30

6:10 am-1:30 pm

1 stop7h 20m

$449

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

Other information

What is the typical price of a round-trip flight between Montego Bay and Chicago?

What is the cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Montego Bay, with most prices found around $146. If you’re not able to fly to Chicago in April, then June is your next best option. Flight prices from Montego Bay to Chicago during June average around $241.

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 $419. 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 $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 Montego Bay 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 $475.

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 3 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 5% 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 April 2026, prices for Montego Bay to Chicago flights are approximately 16% cheaper 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	$224
Fastest flight time	4h 39m
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 $224. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $366.

The fastest flight from Montego Bay to Chicago takes 4h 39m

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 39m 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 3 as of April 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 (31.33% of total bookings). The next most popular plane models are Boeing 737-800 (15.66%), Airbus A321-100/200 (14.46%), and Boeing 737-800 Passenger/BBJ2 (winglets) (8.43%).

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 9,672 reviews	Search United Airlines flights
Southwest	PriceFrom $281	Free Cancellation	Rating 8.0 4,314 reviews	Search Southwest flights
American Airlines	PriceFrom $281	Free Cancellation	Rating 7.1 11,677 reviews	Search American Airlines flights

United Airlines Flights From Montego Bay to Chicago
Across 2 United Airlines flights from Montego Bay to Chicago this week, the average price was $409, with the best United Airlines deals starting from $281 round-trip. 9,672 users have rated United Airlines on momondo, with an average score of 7.4/10.
American Airlines Flights From Montego Bay to Chicago
Across 11,677 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Montego Bay to Chicago about 7 times each week, with ticket deals ranging from $281 to $436. Price data is based on momondo searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Monticello

Chesterton

Porter

Griffith

Saint John

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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Cheap flights from Montego Bay to Chicago from $170

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 5/23. 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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American Airlines flights from Montego Bay to Chicago

Our best American Airlines deals on Montego Bay to Chicago flight tickets

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Our best United Airlines deals on Montego Bay to Chicago flight tickets

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How to get the cheapest flight ticket from Montego Bay to Chicago

What is the typical price of a round-trip flight between Montego Bay and 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?

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

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

When to book flights from Montego Bay to Chicago

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

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

United Airlines Flights From Montego Bay to Chicago

American Airlines Flights From Montego Bay to Chicago

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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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

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

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