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

Orlando (MCO) was the most common stop: 30% of momondo users choosing 1-stop flights on this route connected there.

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 64% of people opting to fly with this airline when traveling to Montego Bay. Keep in mind that there are 6 different airlines that fly to Montego Bay on a routine basis, so you have a few additional options to choose from.

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

Flights connecting via Orlando (MCO) have the shortest average one-way travel time: 5h 40m.

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

As of December 2025, there are 6 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Sat, with 33% of flights taking off on this day.

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?

Orlando (MCO) has the shortest average layover time for this route: 1h 15m.

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

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

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 6 as of December 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.

$104 Cheap Flights from Chicago to Montego Bay in 2025/26

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Find the cheapest flights from Chicago to Montego Bay

Round-trip

One-way

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Cheap round-trip flights

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10:09 am - 3:22 pm

ORD

MBJ

4h 13mnonstop

3:12 pm - 6:51 pm

MBJ

ORD

4h 39mnonstop

$377American Airlines

Mon, Jan 12 - Thu, Jan 15

10:07 am - 12:02 pm

ORD

MBJ

24h 55m2 stops

1:00 pm - 11:47 pm

MBJ

ORD

11h 47m1 stop

$378Spirit Airlines

Sat, Feb 7 - Sun, Feb 22

5:15 am - 12:02 pm

ORD

MBJ

5h 47m1 stop

12:57 pm - 1:13 pm

MBJ

ORD

25h 16m2 stops

$379Spirit Airlines

Thu, Jan 22 - Mon, Jan 26

8:43 pm - 12:02 pm

ORD

MBJ

14h 19m1 stop

12:57 pm - 11:46 pm

MBJ

ORD

11h 49m1 stop

$380Spirit Airlines

Thu, Jan 15 - Mon, Jan 19

5:26 pm - 12:24 pm

ORD

MBJ

17h 58m1 stop

3:12 pm - 6:51 pm

MBJ

ORD

4h 39mnonstop

$381American Airlines

Sat, Jan 24 - Thu, Jan 29

6:45 am - 3:20 pm

MDW

MBJ

7h 35m1 stop

4:45 pm - 10:22 pm

MBJ

MDW

6h 37m1 stop

$435Delta

Sun, Jan 18 - Wed, Jan 21

6:20 pm - 12:32 pm

MDW

MBJ

17h 12m2 stops

4:44 pm - 12:46 pm

MBJ

MDW

21h 02m2 stops

$440Delta

Fri, Feb 27 - Thu, Mar 5

9:04 pm - 9:00 am

MDW

MBJ

10h 56m1 stop

10:40 am - 9:33 pm

MBJ

MDW

11h 53m1 stop

$443Frontier

Sun, Feb 15 - Sat, Feb 21

6:50 am - 2:10 pm

MDW

MBJ

6h 20m1 stop

2:00 pm - 9:00 pm

MBJ

MDW

8h 00m1 stop

$463Southwest

Wed, Feb 18 - Wed, Feb 25

6:50 am - 2:10 pm

MDW

MBJ

6h 20m1 stop

2:00 pm - 10:05 pm

MBJ

MDW

9h 05m2 stops

$468Southwest

Wed, Feb 18 - Wed, Feb 25

Frontier flights from Chicago to Montego Bay

Our best Frontier deals on Chicago to Montego Bay flight tickets

Frontier

Jan 17

ORD6:20 amChicago O'Hare Intl

8h 23m

1 stop

MBJ3:43 pmMontego Bay Sangster Intl

Jan 24

MBJ2:35 pmMontego Bay Sangster Intl

9h 09m

1 stop

ORD10:44 pmChicago O'Hare Intl

$393

Find similar

Frontier

Apr 2

ORD5:05 amChicago O'Hare Intl

9h 41m

1 stop

MBJ2:46 pmMontego Bay Sangster Intl

Apr 13

MBJ4:06 pmMontego Bay Sangster Intl

7h 55m

1 stop

ORD12:01 amChicago O'Hare Intl

$433

Find similar

Frontier

Feb 15

MDW9:04 pmChicago Midway

10h 56m

1 stop

MBJ9:00 amMontego Bay Sangster Intl

Feb 21

MBJ10:40 amMontego Bay Sangster Intl

11h 53m

1 stop

MDW9:33 pmChicago Midway

$443

Find similar

American Airlines flights from Chicago to Montego Bay

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

American Airlines

Jan 12

ORD10:09 amChicago O'Hare Intl

4h 13m

MBJ3:22 pmMontego Bay Sangster Intl

Jan 16

MBJ3:12 pmMontego Bay Sangster Intl

4h 39m

ORD6:51 pmChicago O'Hare Intl

$377

Find similar

American Airlines

Jan 24

ORD5:26 pmChicago O'Hare Intl

17h 58m

1 stop

MBJ12:24 pmMontego Bay Sangster Intl

Jan 29

MBJ3:12 pmMontego Bay Sangster Intl

4h 39m

ORD6:51 pmChicago O'Hare Intl

$381

Find similar

American Airlines

Jan 18

ORD10:09 amChicago O'Hare Intl

4h 13m

MBJ3:22 pmMontego Bay Sangster Intl

Jan 21

MBJ12:33 pmMontego Bay Sangster Intl

11h 54m

1 stop

ORD11:27 pmChicago O'Hare Intl

$387

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/12

10:09 am-3:22 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Thu 1/15

3:12 pm-6:51 pm

Nonstop4h 39m

$377

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 2/7

10:07 am-12:02 pm

2 stops24h 55m

Montego Bay Sangster Intl

Sun 2/22

1:00 pm-11:47 pm

1 stop11h 47m

$378

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 1/22

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Mon 1/26

12:57 pm-1:13 pm

2 stops25h 16m

$379

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 1/15

8:43 pm-12:02 pm

1 stop14h 19m

Montego Bay Sangster Intl

Mon 1/19

12:57 pm-11:46 pm

1 stop11h 49m

$380

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/24

5:26 pm-12:24 pm

1 stop17h 58m

Montego Bay Sangster Intl

Thu 1/29

3:12 pm-6:51 pm

Nonstop4h 39m

$381

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 1/18

6:45 am-3:20 pm

1 stop7h 35m

Montego Bay Sangster Intl

Wed 1/21

4:45 pm-10:22 pm

1 stop6h 37m

$435

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 2/27

6:20 pm-12:32 pm

2 stops17h 12m

Montego Bay Sangster Intl

Thu 3/5

4:44 pm-12:46 pm

2 stops21h 02m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/15

9:04 pm-9:00 am

1 stop10h 56m

Montego Bay Sangster Intl

Sat 2/21

10:40 am-9:33 pm

1 stop11h 53m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/25

2:00 pm-9:00 pm

1 stop8h 00m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/25

2:00 pm-10:05 pm

2 stops9h 05m

$468

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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 September is also cheap. Prices for this month can be found on momondo for an average of $540.

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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $552. 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 $691.

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 $607.

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 $581 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 $546 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?

No. A direct flight is the cheapest option for a flight between Chicago to Montego Bay.

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

As of December 2025, prices for Chicago to Montego Bay flights are approximately 13% cheaper 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	$215
Fastest flight time	3h 50m
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 $215. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $459.

The fastest flight from Chicago to Montego Bay takes 3h 50m

Direct flights go from Chicago to Montego Bay every day.

There is 1 airport in Montego Bay. From Chicago there are direct flights to 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 50m.
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 6 as of December 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 55.40% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 36.90%, Airbus A321-100/200 at 4.94%, and Airbus A220-300 at 0.69%.
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 58% of the total bookings. Other popular airlines include United Airlines with 21%, Southwest with 9%, 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 $174	Free Cancellation	Rating 6.3 8,194 reviews	Search Spirit Airlines flights
Delta	PriceFrom $186	Free Cancellation	Rating 7.9 8,014 reviews	Search Delta flights
Frontier	PriceFrom $341	Free Cancellation	Rating 5.8 3,074 reviews	Search Frontier flights
United Airlines	PriceFrom $356	Free Cancellation	Rating 7.4 9,106 reviews	Search United Airlines flights
American Airlines	PriceFrom $430	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights
Southwest	PriceFrom $549	Free Cancellation	Rating 8.0 4,253 reviews	Search Southwest flights

American Airlines Flights From Chicago to Montego Bay
American Airlines flight deals from Chicago to Montego Bay start from $430 round-trip. Over the 2 American Airlines flights for this route in a normal week, average airfare is usually $590 round-trip - but some users have found much cheaper deals with momondo.

Lucea

Falmouth

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.

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Cheap flights from Chicago to Montego Bay from $104

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 2/3. 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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Frontier flights from Chicago to Montego Bay

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Our best American 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

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 September is also cheap. Prices for this month can be found on momondo for an average of $540.

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?

No. A direct flight is the cheapest option for a flight between Chicago to Montego Bay.

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

As of December 2025, prices for Chicago to Montego Bay flights are approximately 13% cheaper 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 Delta 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?

Orlando (MCO) was the most common stop: 30% 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 Orlando (MCO) have the shortest average one-way travel time: 5h 40m.

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

Orlando (MCO) has the shortest average layover time for this route: 1h 15m.

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

As of December 2025, there are 6 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Sat, with 33% 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.

Find better results for your trip to Jamaica

Airports servicing Jamaica