What airlines fly to Montego Bay?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Montego Bay from Chicago according to our data. American Airlines is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Montego Bay. Keep in mind that there are 5 different airlines that fly to Montego Bay on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Chicago to Montego Bay?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $384.

Which layover airport has the shortest connection time from Chicago to Montego Bay?

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 18m.

Which layover airport has the shortest travel time from Chicago to Montego Bay?

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 26m.

Which airport is the most popular layover for flights between Chicago and Montego Bay?

Fort Lauderdale (FLL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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

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

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

As of August 2025, there are 1 flights per day flying from Chicago to Montego Bay. The most common time of day flights depart is 8:00AM, with 100% of flights taking off at noon.

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

As of August 2025, there are 7 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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

Prices for flights from Chicago to Montego Bay Sangster Intl Airport refresh daily.

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

The number of operators available for flights from Chicago to Montego Bay Sangster Intl Airport is 5 as of August 2025.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Montego Bay Sangster Intl Airport.

What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?

The required travel and health documents for your Montego Bay Sangster Intl Airport 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 Montego Bay Sangster Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$103 Cheap Flights from Chicago to Montego Bay (CHI-MBJ) in 2025

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

Prices are currently low for flights on this route. Typical prices usually range from $490 to $659. The lowest price recently found on this route was $397.

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Find the cheapest flights from Chicago to Montego Bay (CHI-MBJ)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:44 pm - 11:05 amORD-MBJ

16h 21m1 stop

12:10 pm - 9:51 amMBJ-ORD

21h 41m2 stops

$397

Find Deal

Sat, Sep 20 - Tue, Sep 23

5:05 am - 1:20 pmORD-MBJ

8h 15m1 stop

12:10 pm - 10:48 pmMBJ-ORD

10h 38m1 stop

$398

Find Deal

Wed, Sep 17 - Thu, Sep 18

5:05 am - 11:00 amORD-MBJ

5h 55m1 stop

12:09 pm - 12:31 pmMBJ-ORD

24h 22m3 stops

$399Spirit Airlines

Find Deal

Tue, Oct 7 - Wed, Oct 8

5:00 am - 1:01 pmORD-MBJ

7h 01m1 stop

3:14 pm - 6:55 pmMBJ-ORD

4h 41mnonstop

$400American Airlines

Find Deal

Fri, Nov 14 - Fri, Nov 21

5:17 pm - 11:05 amORD-MBJ

41h 48m2 stops

12:10 pm - 10:48 pmMBJ-ORD

10h 38m1 stop

$401Spirit Airlines

Find Deal

Thu, Sep 18 - Thu, Sep 25

8:42 am - 12:46 pmORD-MBJ

4h 04mnonstop

3:20 pm - 12:15 amMBJ-ORD

9h 55m1 stop

$405United Airlines

Find Deal

Wed, Oct 29 - Sun, Nov 2

8:05 am - 1:04 pmORD-MBJ

3h 59mnonstop

3:53 pm - 10:25 amMBJ-ORD

19h 32m1 stop

$412American Airlines

Find Deal

Thu, Nov 13 - Tue, Nov 18

7:00 am - 2:00 pmMDW-MBJ

7h 00m1 stop

12:55 pm - 7:10 amMBJ-MDW

18h 15m2 stops

$439Southwest

Find Deal

Sat, Sep 13 - Wed, Sep 24

8:42 am - 12:46 pmORD-MBJ

4h 04mnonstop

2:48 pm - 6:13 pmMBJ-ORD

4h 25mnonstop

$448United Airlines

Find Deal

Sat, Nov 1 - Tue, Nov 4

7:00 am - 2:00 pmMDW-MBJ

7h 00m1 stop

12:55 pm - 9:40 pmMBJ-MDW

8h 45m1 stop

$450Southwest

Find Deal

Sat, Sep 13 - Wed, Sep 24

American Airlines flights from Chicago to Montego Bay

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

American Airlines

Nov 14

ORD5:00 amChicago O'Hare Intl

7h 01m

1 stop

MBJ1:01 pmMontego Bay Sangster Intl

Nov 21

MBJ3:14 pmMontego Bay Sangster Intl

4h 41m

ORD6:55 pmChicago O'Hare Intl

$400

Find similar

American Airlines

Nov 13

ORD8:05 amChicago O'Hare Intl

3h 59m

MBJ1:04 pmMontego Bay Sangster Intl

Nov 18

MBJ3:53 pmMontego Bay Sangster Intl

19h 32m

1 stop

ORD10:25 amChicago O'Hare Intl

$412

Find similar

American Airlines

Sep 11

ORD8:45 pmChicago O'Hare Intl

18h 09m

1 stop

MBJ2:54 pmMontego Bay Sangster Intl

Sep 18

MBJ2:38 pmMontego Bay Sangster Intl

9h 01m

2 stops

ORD11:39 pmChicago O'Hare Intl

$422

Find similar

Spirit Airlines flights from Chicago to Montego Bay

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

Spirit Airlines

Oct 7

ORD5:05 amChicago O'Hare Intl

5h 55m

1 stop

MBJ11:00 amMontego Bay Sangster Intl

Oct 8

MBJ12:09 pmMontego Bay Sangster Intl

24h 22m

3 stops

ORD12:31 pmChicago O'Hare Intl

$399

Find similar

Spirit Airlines

Sep 18

ORD5:17 pmChicago O'Hare Intl

41h 48m

2 stops

MBJ11:05 amMontego Bay Sangster Intl

Sep 25

MBJ12:10 pmMontego Bay Sangster Intl

10h 38m

1 stop

ORD10:48 pmChicago O'Hare Intl

$401

Find similar

Spirit Airlines

Oct 5

ORD6:16 pmChicago O'Hare Intl

16h 44m

2 stops

MBJ11:00 amMontego Bay Sangster Intl

Oct 12

MBJ12:09 pmMontego Bay Sangster Intl

6h 27m

1 stop

ORD6:36 pmChicago O'Hare Intl

$402

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 9/20

6:44 pm-11:05 am

1 stop16h 21m

Montego Bay Sangster Intl

Tue 9/23

12:10 pm-9:51 am

2 stops21h 41m

$397

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 9/17

5:05 am-1:20 pm

1 stop8h 15m

Montego Bay Sangster Intl

Thu 9/18

12:10 pm-10:48 pm

1 stop10h 38m

$398

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 10/7

5:05 am-11:00 am

1 stop5h 55m

Montego Bay Sangster Intl

Wed 10/8

12:09 pm-12:31 pm

3 stops24h 22m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 11/14

5:00 am-1:01 pm

1 stop7h 01m

Montego Bay Sangster Intl

Fri 11/21

3:14 pm-6:55 pm

Nonstop4h 41m

$400

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 9/18

5:17 pm-11:05 am

2 stops41h 48m

Montego Bay Sangster Intl

Thu 9/25

12:10 pm-10:48 pm

1 stop10h 38m

$401

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 10/29

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sun 11/2

3:20 pm-12:15 am

1 stop9h 55m

$405

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 11/13

8:05 am-1:04 pm

Nonstop3h 59m

Montego Bay Sangster Intl

Tue 11/18

3:53 pm-10:25 am

1 stop19h 32m

$412

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/13

7:00 am-2:00 pm

1 stop7h 00m

Montego Bay Sangster Intl

Wed 9/24

12:55 pm-7:10 am

2 stops18h 15m

$439

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/1

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Tue 11/4

2:48 pm-6:13 pm

Nonstop4h 25m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/13

7:00 am-2:00 pm

1 stop7h 00m

Montego Bay Sangster Intl

Wed 9/24

12:55 pm-9:40 pm

1 stop8h 45m

$450

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 Chicago to Montego Bay

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

Layovers

Other information

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

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $534.

What is the cheapest day to depart on your flight to Montego Bay?

On average, the least expensive day to fly to Montego Bay from Chicago is on a Sunday. momondo users have found tickets for Sunday departures for as low as $538. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Montego Bay on Thursday is $680.

What is the cheapest time of day to depart on your flight to Montego Bay?

At noon is the cheapest time of day to fly from Chicago to Montego Bay when you can find flight prices for as low as $403. Flying to Montego Bay at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $608.

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

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

How far in advance should I book a flight to Montego Bay?

You are more likely to see cheaper flights to Montego Bay from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Montego Bay for around $607 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Montego Bay from Chicago for as low as $532 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to Montego Bay Sangster Intl 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 Chicago to Montego Bay flights?

You could potentially save up to 19% on your flight if you consider stops on a Chicago to Montego Bay flight.

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

As of August 2025, prices for Chicago to Montego Bay flights are approximately 4% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Montego Bay

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

Estimated round-trip price

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

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

Best Price Found	$197
Fastest flight time	3h 55m
Direct flights	Every day
Airports in Montego Bay	1 airport

The best one-way flight to Montego Bay from Chicago in the past 72 hours is $197. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $522.

The fastest flight from Chicago to Montego Bay takes 3h 55m

Direct flights go from Chicago to Montego Bay every day.

There is 1 airport near Montego Bay: Montego Bay Sangster Intl (MBJ)

Search flight deals

How far is Chicago to Montego Bay Sangster Intl by plane?
The distance between Chicago and Montego Bay Sangster Intl is about 1713.9 mi. A reasonable flight in good conditions will take 3h 59m.
When did momondo last update prices for flights from Chicago to Montego Bay Sangster Intl Airport?
Prices for flights from Chicago to Montego Bay Sangster Intl Airport refresh daily.
How many operators does momondo search for flights from Chicago to Montego Bay Sangster Intl Airport?
The number of operators available for flights from Chicago to Montego Bay Sangster Intl Airport is 5 as of August 2025.
How old do you have to be to fly from Chicago to Montego Bay Sangster Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Montego Bay Sangster Intl Airport.
What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?
The required travel and health documents for your Montego Bay Sangster Intl Airport 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 Montego Bay Sangster Intl Airport. 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 Chicago to Montego Bay?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Montego Bay is Boeing 737-800, representing 62.50% of all bookings. The subsequent popular models are Airbus A321-100/200 at 18.10%, Boeing 737 MAX 8 at 12.11%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 5.73%.
What is the most popular airline from Chicago to Montego Bay?
Based on momondo bookings for flights between Chicago and Montego Bay, the leading airline is American Airlines, making up 57% of the total bookings. Other popular airlines include United Airlines with 23%, Southwest with 7%, and Spirit Airlines with 7%.

Best airlines flying from Chicago to Montego Bay

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $266	Free Cancellation	Rating 6.3 8,028 reviews	Search Spirit Airlines flights
Delta	PriceFrom $312	Free Cancellation	Rating 7.9 7,981 reviews	Search Delta flights
United Airlines	PriceFrom $424	Free Cancellation	Rating 7.4 8,940 reviews	Search United Airlines flights
American Airlines	PriceFrom $443	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $549	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights

American Airlines Flights From Chicago to Montego Bay
American Airlines flight deals from Chicago to Montego Bay start from $443 round-trip. Over the 7 American Airlines flights for this route in a normal week, average airfare is usually $600 round-trip - but some users have found much cheaper deals with momondo.

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Treasure Beach

Whitehouse

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Montego Bay. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Chicago to Montego Bay with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Montego Bay from Chicago.

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

Yes momondo offers price alerts on flights to Montego Bay from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Montego Bay 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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Cheap flights from Chicago to Montego Bay from $103

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Montego Bay departing on 9/20. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Montego Bay (CHI-MBJ)

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American Airlines flights from Chicago to Montego Bay

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

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

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See travel insights to Montego Bay from

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

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 Chicago and Montego Bay?

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $534.

What is the cheapest day to depart on your flight to Montego Bay?

What is the cheapest time of day to depart on your flight to Montego Bay?

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

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

How far in advance should I book a flight to Montego Bay?

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

There are 3 cabin classes available to choose from on Chicago to Montego Bay Sangster Intl 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 Chicago to Montego Bay flights?

You could potentially save up to 19% on your flight if you consider stops on a Chicago to Montego Bay flight.

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

As of August 2025, prices for Chicago to Montego Bay flights are approximately 4% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Montego Bay?

Which airport is the most popular layover for flights between Chicago and Montego Bay?

Fort Lauderdale (FLL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Montego Bay?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $384.

Which layover airport has the shortest travel time from Chicago to Montego Bay?

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 26m.

Which layover airport has the shortest connection time from Chicago to Montego Bay?

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 18m.

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

As of August 2025, there are 1 flights per day flying from Chicago to Montego Bay. The most common time of day flights depart is 8:00AM, with 100% of flights taking off at noon.

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

As of August 2025, there are 7 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

When to book flights from Chicago to Montego Bay

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Montego Bay

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

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

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

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

What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?

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

What is the most popular airline from Chicago to Montego Bay?

Best airlines flying from Chicago to Montego Bay

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

American Airlines Flights From Chicago to Montego Bay

Traveling to a place near Montego Bay?

Why use momondo?

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

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

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

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

An easier way to manage your Montego Bay 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.