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 67% 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 airport is the most popular layover for flights between Chicago and Montego Bay?

Fort Lauderdale (FLL) was the most common stop: 36% of momondo users choosing 1-stop flights on this route connected there.

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 February 2026, 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.

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.

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

As of February 2026, 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.

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

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

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.

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 February 2026.

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.

$118 Cheap Flights from Chicago to Montego Bay in 2026

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 $511 to $858. The lowest price recently found on this route was $293.

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Find the cheapest flights from Chicago to Montego Bay

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:05 am - 12:13 pm

ORD

MBJ

4h 08mnonstop

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

$293American Airlines

Tue, May 12 - Sun, May 17

8:53 pm - 3:20 pm

ORD

MBJ

18h 27m

1 stop

2:00 pm - 6:30 pm

MBJ

ORD

4h 30mnonstop

$294American Airlines

Sat, Aug 1 - Thu, Aug 6

7:15 am - 1:25 pm

ORD

MBJ

6h 10m

1 stop

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

$297American Airlines

Wed, Apr 15 - Sun, Apr 19

8:42 am - 12:46 pm

ORD

MBJ

4h 04mnonstop

1:48 pm - 6:13 pm

MBJ

ORD

4h 25mnonstop

$298United Airlines

Wed, Mar 11 - Wed, Mar 18

8:46 pm - 9:13 am

ORD

MBJ

12h 27m

1 stop

2:29 pm - 4:21 pm

MBJ

ORD

25h 52m

1 stop

$299American Airlines

Sat, May 9 - Fri, May 15

5:28 pm - 9:07 am

ORD

MBJ

15h 39m

1 stop

10:07 am - 8:53 am

MBJ

ORD

22h 46m

1 stop

$300American Airlines

Mon, Mar 23 - Thu, Mar 26

5:05 am - 11:05 am

ORD

MBJ

6h 00m

1 stop

12:00 pm - 8:03 am

MBJ

ORD

20h 03m

2 stops

$305Spirit Airlines

Tue, Apr 14 - Wed, Apr 22

9:55 am - 1:45 pm

MDW

MBJ

3h 50mnonstop

11:35 am - 3:45 pm

MBJ

MDW

4h 10mnonstop

$354Southwest

Sat, May 16 - Sat, May 23

7:50 am - 11:45 am

MDW

MBJ

3h 55mnonstop

1:50 pm - 5:50 pm

MBJ

MDW

4h 00mnonstop

$373Southwest

Sun, Jun 7 - Thu, Jun 11

9:16 pm - 12:42 pm

MDW

MBJ

15h 26m

1 stop

1:59 pm - 7:00 am

MBJ

MDW

17h 01m

1 stop

$412Frontier

Thu, May 28 - Thu, Jun 4

American Airlines flights from Chicago to Montego Bay

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

American Airlines

May 12

ORD8:05 amChicago O'Hare Intl

4h 08m

MBJ12:13 pmMontego Bay Sangster Intl

May 17

MBJ1:15 pmMontego Bay Sangster Intl

4h 40m

ORD5:55 pmChicago O'Hare Intl

$293

American Airlines

Aug 1

ORD8:53 pmChicago O'Hare Intl

18h 27m

1 stop

MBJ3:20 pmMontego Bay Sangster Intl

Aug 6

MBJ2:00 pmMontego Bay Sangster Intl

4h 30m

ORD6:30 pmChicago O'Hare Intl

$294

American Airlines

Apr 15

ORD7:15 amChicago O'Hare Intl

6h 10m

1 stop

MBJ1:25 pmMontego Bay Sangster Intl

Apr 19

MBJ1:15 pmMontego Bay Sangster Intl

4h 40m

ORD5:55 pmChicago O'Hare Intl

$297

Delta flights from Chicago to Montego Bay

Our best Delta deals on Chicago to Montego Bay flight tickets

Delta

Mar 1

MDW7:20 pmChicago Midway

18h 20m

1 stop

MBJ2:40 pmMontego Bay Sangster Intl

Mar 4

MBJ4:05 pmMontego Bay Sangster Intl

18h 01m

1 stop

MDW9:06 amChicago Midway

$452

Delta

Mar 9

MDW6:07 pmChicago Midway

15h 53m

1 stop

MBJ10:00 amMontego Bay Sangster Intl

Mar 18

MBJ4:49 pmMontego Bay Sangster Intl

19h 40m

2 stops

MDW12:29 pmChicago Midway

$457

Delta

Jun 5

MDW6:23 amChicago Midway

6h 33m

1 stop

MBJ12:56 pmMontego Bay Sangster Intl

Jun 10

MBJ2:30 pmMontego Bay Sangster Intl

7h 15m

1 stop

MDW9:45 pmChicago Midway

$497

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/12

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Sun 5/17

1:15 pm-5:55 pm

Nonstop4h 40m

$293

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 8/1

8:53 pm-3:20 pm

1 stop18h 27m

Montego Bay Sangster Intl

Thu 8/6

2:00 pm-6:30 pm

Nonstop4h 30m

$294

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 4/15

7:15 am-1:25 pm

1 stop6h 10m

Montego Bay Sangster Intl

Sun 4/19

1:15 pm-5:55 pm

Nonstop4h 40m

$297

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/11

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Wed 3/18

1:48 pm-6:13 pm

Nonstop4h 25m

$298

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 5/9

8:46 pm-9:13 am

1 stop12h 27m

Montego Bay Sangster Intl

Fri 5/15

2:29 pm-4:21 pm

1 stop25h 52m

$299

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 3/23

5:28 pm-9:07 am

1 stop15h 39m

Montego Bay Sangster Intl

Thu 3/26

10:07 am-8:53 am

1 stop22h 46m

$300

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/14

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

Wed 4/22

12:00 pm-8:03 am

2 stops20h 03m

$305

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/16

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 5/23

11:35 am-3:45 pm

Nonstop4h 10m

$354

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 6/7

7:50 am-11:45 am

Nonstop3h 55m

Montego Bay Sangster Intl

Thu 6/11

1:50 pm-5:50 pm

Nonstop4h 00m

$373

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 5/28

9:16 pm-12:42 pm

1 stop15h 26m

Montego Bay Sangster Intl

Thu 6/4

1:59 pm-7:00 am

1 stop17h 01m

$412

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 April is also cheap. Prices for this month can be found on momondo for an average of $531.

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 $539. 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 $676.

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 $568 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 $493 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 16% 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 February 2026, prices for Chicago to Montego Bay flights are approximately 5% 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	$180
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 $180. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $464.

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 February 2026.
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 58.77% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 36.02%, Airbus A321-100/200 at 1.90%, and Boeing 737-900 at 1.42%.
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 59% of the total bookings. Other popular airlines include United Airlines with 19%, Southwest with 10%, 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 $141	Free Cancellation	Rating 6.3 8,493 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $144	Free Cancellation	Rating 5.7 3,041 reviews	Search Frontier flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 8,242 reviews	Search Delta flights
United Airlines	PriceFrom $356	Free Cancellation	Rating 7.4 9,351 reviews	Search United Airlines flights
American Airlines	PriceFrom $404	Free Cancellation	Rating 7.2 11,357 reviews	Search American Airlines flights
Southwest	PriceFrom $518	Free Cancellation	Rating 8.0 4,301 reviews	Search Southwest flights

American Airlines Flights From Chicago to Montego Bay
American Airlines flight deals from Chicago to Montego Bay start from $404 round-trip. Over the 7 American Airlines flights for this route in a normal week, average airfare is usually $573 round-trip - but some users have found much cheaper deals with momondo.

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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 $118

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 5/4. 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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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?

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

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

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?

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

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

What is the cheapest airline that flies 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?

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

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

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

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

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

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

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?

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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