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

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 66% 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 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.

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

As of February 2026, there are 4 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Mon, with 25% of flights taking off on this day.

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

Fort Lauderdale (FLL) was the most common stop: 27% of momondo users choosing 1-stop flights on this route connected there.

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.

$98 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 $486 to $679. The lowest price recently found on this route was $364.

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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.

6:20 am - 9:17 am

ORD

MBJ

25h 57m

2 stops

12:40 pm - 10:39 pm

MBJ

ORD

10h 59m

1 stop

$364Frontier

sáb., feb. 21 - sáb., feb. 28

6:00 am - 3:19 pm

MDW

MBJ

8h 19m

1 stop

4:44 pm - 10:31 pm

MBJ

MDW

6h 47m

1 stop

$364Delta

dom., feb. 22 - jue., feb. 26

4:42 pm - 9:17 am

ORD

MBJ

15h 35m

1 stop

1:00 pm - 11:47 pm

MBJ

ORD

11h 47m

1 stop

$365Multiple Airlines

sáb., feb. 14 - mié., feb. 18

10:19 am - 12:02 pm

ORD

MBJ

24h 43m

2 stops

12:00 pm - 7:51 pm

MBJ

ORD

7h 51m

1 stop

$366Spirit Airlines

lun., feb. 16 - jue., mar. 12

8:20 am - 1:26 pm

ORD

MBJ

4h 06mnonstop

10:07 am - 6:28 pm

MBJ

ORD

8h 21m

1 stop

$367American Airlines

mar., mar. 3 - mar., mar. 10

8:00 am - 9:17 am

MDW

MBJ

24h 17m

2 stops

12:40 pm - 9:39 pm

MBJ

MDW

9h 59m

1 stop

$367Frontier

sáb., feb. 21 - sáb., feb. 28

4:42 pm - 9:17 am

ORD

MBJ

15h 35m

1 stop

1:00 pm - 9:13 pm

MBJ

ORD

9h 13m

1 stop

$368Multiple Airlines

sáb., feb. 21 - mar., feb. 24

5:15 am - 12:02 pm

ORD

MBJ

5h 47m

1 stop

1:00 pm - 9:13 pm

MBJ

ORD

9h 13m

1 stop

$371Spirit Airlines

sáb., feb. 21 - sáb., feb. 28

6:50 am - 2:10 pm

MDW

MBJ

6h 20m

1 stop

12:55 pm - 8:50 pm

MBJ

MDW

7h 55m

1 stop

$396Southwest

mié., mar. 4 - mié., mar. 11

5:00 am - 1:00 pm

MDW

MBJ

7h 00m

1 stop

12:55 pm - 10:50 pm

MBJ

MDW

9h 55m

2 stops

$397Southwest

mar., mar. 3 - mar., mar. 10

American Airlines flights from Chicago to Montego Bay

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

American Airlines

Mar 3

ORD8:20 amChicago O'Hare Intl

4h 06m

MBJ1:26 pmMontego Bay Sangster Intl

Mar 10

MBJ10:07 amMontego Bay Sangster Intl

8h 21m

1 stop

ORD6:28 pmChicago O'Hare Intl

$367

American Airlines

Mar 5

ORD5:29 pmChicago O'Hare Intl

15h 38m

1 stop

MBJ10:07 amMontego Bay Sangster Intl

Mar 11

MBJ1:14 pmMontego Bay Sangster Intl

4h 41m

ORD5:55 pmChicago O'Hare Intl

$386

American Airlines

Mar 6

ORD8:20 amChicago O'Hare Intl

4h 06m

MBJ1:26 pmMontego Bay Sangster Intl

Mar 10

MBJ12:21 pmMontego Bay Sangster Intl

8h 57m

1 stop

ORD9:18 pmChicago O'Hare Intl

$392

Spirit Airlines flights from Chicago to Montego Bay

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

Spirit Airlines

Feb 16

ORD10:19 amChicago O'Hare Intl

24h 43m

2 stops

MBJ12:02 pmMontego Bay Sangster Intl

Mar 12

MBJ12:00 pmMontego Bay Sangster Intl

7h 51m

1 stop

ORD7:51 pmChicago O'Hare Intl

$366

Spirit Airlines

Feb 21

ORD5:15 amChicago O'Hare Intl

5h 47m

1 stop

MBJ12:02 pmMontego Bay Sangster Intl

Feb 28

MBJ1:00 pmMontego Bay Sangster Intl

9h 13m

1 stop

ORD9:13 pmChicago O'Hare Intl

$371

Spirit Airlines

Mar 18

ORD6:10 pmChicago O'Hare Intl

16h 55m

1 stop

MBJ11:05 amMontego Bay Sangster Intl

Mar 31

MBJ12:00 pmMontego Bay Sangster Intl

23h 50m

2 stops

ORD11:50 amChicago O'Hare Intl

$372

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 2/21

6:20 am-9:17 am

2 stops25h 57m

Montego Bay Sangster Intl

sáb. 2/28

12:40 pm-10:39 pm

1 stop10h 59m

$364

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 2/22

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

jue. 2/26

4:44 pm-10:31 pm

1 stop6h 47m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 2/14

4:42 pm-9:17 am

1 stop15h 35m

Montego Bay Sangster Intl

mié. 2/18

1:00 pm-11:47 pm

1 stop11h 47m

$365

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 2/16

10:19 am-12:02 pm

2 stops24h 43m

Montego Bay Sangster Intl

jue. 3/12

12:00 pm-7:51 pm

1 stop7h 51m

$366

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 3/3

8:20 am-1:26 pm

Nonstop4h 06m

Montego Bay Sangster Intl

mar. 3/10

10:07 am-6:28 pm

1 stop8h 21m

$367

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 2/21

8:00 am-9:17 am

2 stops24h 17m

Montego Bay Sangster Intl

sáb. 2/28

12:40 pm-9:39 pm

1 stop9h 59m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 2/21

4:42 pm-9:17 am

1 stop15h 35m

Montego Bay Sangster Intl

mar. 2/24

1:00 pm-9:13 pm

1 stop9h 13m

$368

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 2/21

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

sáb. 2/28

1:00 pm-9:13 pm

1 stop9h 13m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 3/4

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

mié. 3/11

12:55 pm-8:50 pm

1 stop7h 55m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 3/3

5:00 am-1:00 pm

1 stop7h 00m

Montego Bay Sangster Intl

mar. 3/10

12:55 pm-10:50 pm

2 stops9h 55m

$397

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 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 $550. 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 $682.

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 $578 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 $504 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 February 2026, prices for Chicago to Montego Bay flights are approximately 7% 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	$204
Fastest flight time	3h 45m
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 $204. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $482.

The fastest flight from Chicago to Montego Bay takes 3h 45m

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 45m.
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 56.54% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 36.91%, Airbus A321-100/200 at 2.85%, and Boeing 737-900 at 1.51%.
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 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 $130	Free Cancellation	Rating 6.3 8,396 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $144	Free Cancellation	Rating 5.7 3,051 reviews	Search Frontier flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 8,132 reviews	Search Delta flights
United Airlines	PriceFrom $356	Free Cancellation	Rating 7.4 9,231 reviews	Search United Airlines flights
American Airlines	PriceFrom $413	Free Cancellation	Rating 7.2 11,212 reviews	Search American Airlines flights
Southwest	PriceFrom $518	Free Cancellation	Rating 8.0 4,271 reviews	Search Southwest flights

American Airlines Flights From Chicago to Montego Bay
American Airlines flight deals from Chicago to Montego Bay start from $413 round-trip. Over the 4 American Airlines flights for this route in a normal week, average airfare is usually $578 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.

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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jue. 3/12

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Flights from Chicago O'Hare Intl to Fort Lauderdale

Cheap flights from Chicago to Montego Bay from $98

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 2/24. 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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Filter for what you want

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American Airlines flights from Chicago to Montego Bay

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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

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 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 February 2026, prices for Chicago to Montego Bay flights are approximately 7% 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, United Airlines, and Southwest 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: 27% 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 February 2026, there are 4 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Mon, with 25% 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