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

The number of flights available between Montego Bay and Chicago is 18 per week as of November 2025. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.

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

Frontier, Spirit Airlines, and United Airlines are the most popular carriers operating from Montego Bay Sangster Intl to 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 Montego Bay according to our data. American Airlines is the first choice among our users, with 53% 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 day?

2 flights are operational daily from Montego Bay to Chicago as of November 2025. The most popular departure time for this route is 2:00PM, with 100% of flights per day taking off in the afternoon.

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 4 as of November 2025.

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.

$165 Cheap Flights from Montego Bay to Chicago in 2025/26

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 $323 to $515. The lowest price recently found on this route was $294.

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1:05 pm - 12:09 amMBJ-ORD

12h 04m1 stop

5:00 am - 12:10 pmORD-MBJ

6h 10m1 stop

$294Spirit Airlines

Find Deal

Thu, Dec 11 - Sun, Dec 14

1:05 pm - 9:48 pmMBJ-ORD

9h 43m2 stops

5:00 am - 12:10 pmORD-MBJ

6h 10m1 stop

$309Spirit Airlines

Find Deal

Thu, Dec 11 - Sun, Dec 14

3:12 pm - 6:59 pmMBJ-ORD

4h 47mnonstop

8:10 am - 1:20 pmORD-MBJ

4h 10mnonstop

$320American Airlines

Find Deal

Thu, Dec 11 - Sun, Dec 14

2:48 pm - 6:13 pmMBJ-ORD

4h 25mnonstop

8:42 am - 1:46 pmORD-MBJ

4h 04mnonstop

$324United Airlines

Find Deal

Wed, Dec 3 - Wed, Dec 10

3:12 pm - 6:59 pmMBJ-ORD

4h 47mnonstop

5:00 am - 2:47 pmORD-MBJ

8h 47m1 stop

$325American Airlines

Find Deal

Thu, Dec 11 - Sun, Dec 14

2:29 pm - 10:43 pmMBJ-ORD

9h 14m1 stop

6:45 am - 2:13 pmORD-MBJ

6h 28m1 stop

$326Delta

Find Deal

Wed, Dec 3 - Wed, Dec 10

3:36 pm - 11:32 pmMBJ-ORD

8h 56m1 stop

9:15 pm - 4:12 pmORD-MBJ

17h 57m1 stop

$330United Airlines

Find Deal

Fri, Dec 12 - Fri, Jan 2

1:05 pm - 6:39 pmMBJ-ORD

6h 34m1 stop

5:05 am - 3:46 pmORD-MBJ

9h 41m1 stop

$357Multiple Airlines

Find Deal

Wed, Dec 31 - Sat, Jan 10

1:05 pm - 8:01 pmMBJ-ORD

7h 56m1 stop

6:00 am - 2:29 pmORD-MBJ

7h 29m1 stop

$379Multiple Airlines

Find Deal

Thu, Dec 11 - Thu, Dec 18

3:38 pm - 11:47 pmMBJ-MDW

9h 09m1 stop

5:29 pm - 11:09 amMDW-MBJ

16h 40m1 stop

$402Delta

Find Deal

Wed, Dec 10 - Wed, Dec 17

United Airlines flights from Montego Bay to Chicago

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

United Airlines

Dec 3

MBJ2:48 pmMontego Bay Sangster Intl

4h 25m

ORD6:13 pmChicago O'Hare Intl

Dec 10

ORD8:42 amChicago O'Hare Intl

4h 04m

MBJ1:46 pmMontego Bay Sangster Intl

$324

Find similar

United Airlines

Dec 12

MBJ3:36 pmMontego Bay Sangster Intl

8h 56m

1 stop

ORD11:32 pmChicago O'Hare Intl

Jan 2

ORD9:15 pmChicago O'Hare Intl

17h 57m

1 stop

MBJ4:12 pmMontego Bay Sangster Intl

$330

Find similar

United Airlines

Nov 13

MBJ2:48 pmMontego Bay Sangster Intl

4h 25m

ORD6:13 pmChicago O'Hare Intl

Nov 30

ORD8:42 amChicago O'Hare Intl

4h 04m

MBJ1:46 pmMontego Bay Sangster Intl

$355

Find similar

Delta flights from Montego Bay to Chicago

Our best Delta deals on Montego Bay to Chicago flight tickets

Delta

Dec 3

MBJ2:29 pmMontego Bay Sangster Intl

9h 14m

1 stop

ORD10:43 pmChicago O'Hare Intl

Dec 10

ORD6:45 amChicago O'Hare Intl

6h 28m

1 stop

MBJ2:13 pmMontego Bay Sangster Intl

$326

Find similar

Delta

Dec 10

MBJ3:38 pmMontego Bay Sangster Intl

9h 09m

1 stop

MDW11:47 pmChicago Midway

Dec 17

MDW5:29 pmChicago Midway

16h 40m

1 stop

MBJ11:09 amMontego Bay Sangster Intl

$402

Find similar

Delta

Nov 26

MBJ2:17 pmMontego Bay Sangster Intl

10h 23m

1 stop

MDW11:40 pmChicago Midway

Dec 1

MDW6:00 amChicago Midway

7h 11m

1 stop

MBJ2:11 pmMontego Bay Sangster Intl

$446

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Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/11

1:05 pm-12:09 am

1 stop12h 04m

Chicago O'Hare Intl

Sun 12/14

5:00 am-12:10 pm

1 stop6h 10m

$294

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/11

1:05 pm-9:48 pm

2 stops9h 43m

Chicago O'Hare Intl

Sun 12/14

5:00 am-12:10 pm

1 stop6h 10m

$309

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/11

3:12 pm-6:59 pm

Nonstop4h 47m

Chicago O'Hare Intl

Sun 12/14

8:10 am-1:20 pm

Nonstop4h 10m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/3

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Wed 12/10

8:42 am-1:46 pm

Nonstop4h 04m

$324

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/11

3:12 pm-6:59 pm

Nonstop4h 47m

Chicago O'Hare Intl

Sun 12/14

5:00 am-2:47 pm

1 stop8h 47m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/3

2:29 pm-10:43 pm

1 stop9h 14m

Chicago O'Hare Intl

Wed 12/10

6:45 am-2:13 pm

1 stop6h 28m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

3:36 pm-11:32 pm

1 stop8h 56m

Chicago O'Hare Intl

Fri 1/2

9:15 pm-4:12 pm

1 stop17h 57m

$330

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 12/31

1:05 pm-6:39 pm

1 stop6h 34m

Chicago O'Hare Intl

Sat 1/10

5:05 am-3:46 pm

1 stop9h 41m

$357

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 12/11

1:05 pm-8:01 pm

1 stop7h 56m

Chicago O'Hare Intl

Thu 12/18

6:00 am-2:29 pm

1 stop7h 29m

$379

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/10

3:38 pm-11:47 pm

1 stop9h 09m

Chicago Midway

Wed 12/17

5:29 pm-11:09 am

1 stop16h 40m

$402

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 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 Montego Bay to Chicago for around $633.

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 $501.

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 Sangster Intl to Chicago flights?

There are 3 cabin classes available to choose from on Montego Bay Sangster Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of November 2025, prices for Montego Bay to Chicago flights are approximately 1% 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	$234
Fastest flight time	4h 10m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Montego Bay in the past 72 hours is $234. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $344.

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

Direct flights go from Montego Bay to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

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 25m 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 4 as of November 2025.
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 (43.14% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (10.78%), Airbus A321-100/200 (5.88%), and Boeing 737-800 (5.88%).
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
Spirit Airlines	PriceFrom $251	Free Cancellation	Rating 6.3 8,114 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $348	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
Southwest	PriceFrom $392	Free Cancellation	Rating 8.0 4,240 reviews	Search Southwest flights
United Airlines	PriceFrom $409	Free Cancellation	Rating 7.4 9,003 reviews	Search United Airlines flights

United Airlines Flights From Montego Bay to Chicago
Across 7 United Airlines flights from Montego Bay to Chicago this week, the average price was $484, with the best United Airlines deals starting from $409 round-trip. 9,003 users have rated United Airlines on momondo, with an average score of 7.4/10.
American Airlines Flights From Montego Bay to Chicago
Across 11,041 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Montego Bay to Chicago about 11 times each week, with ticket deals ranging from $348 to $481. Price data is based on momondo searches in the last 72 hours.

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Saint Joseph

Portage

Lansing

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 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 $165

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 1/15. 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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Big names and deals

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United Airlines flights from Montego Bay to Chicago

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

Delta flights from Montego Bay to Chicago

Our best Delta deals on Montego Bay to Chicago flight tickets

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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

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

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 $501.

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 Sangster Intl to Chicago flights?

There are 3 cabin classes available to choose from on Montego Bay Sangster Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of November 2025, prices for Montego Bay to Chicago flights are approximately 1% cheaper when compared to flights at the same time last year.

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

Frontier, Spirit Airlines, and United Airlines are the most popular carriers operating 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?

2 flights are operational daily from Montego Bay to Chicago as of November 2025. The most popular departure time for this route is 2:00PM, with 100% of flights per day taking off in the afternoon.

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

The number of flights available between Montego Bay and Chicago is 18 per week as of November 2025. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.

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

How far is Montego Bay Sangster Intl to Chicago by plane?

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

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

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

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

What is the most popular plane model from Montego Bay to Chicago?

What is the most popular airline 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?

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

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

How can momondo help me find flights 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?

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