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.

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

Southwest, American Airlines, and United Airlines 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 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.

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.

$111 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 $489 to $687. 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.

12:44 pm - 12:02 pm

ORD

MBJ

22h 18m

3 stops

11:57 am - 7:11 pm

MBJ

ORD

7h 14m

1 stop

$364Spirit Airlines

Tue, Mar 3 - Tue, Mar 10

5:00 am - 1:25 pm

ORD

MBJ

8h 25m

1 stop

4:37 pm - 2:39 pm

MBJ

ORD

22h 02m

1 stop

$365American Airlines

Thu, Apr 16 - Mon, Apr 20

6:05 am - 1:25 pm

ORD

MBJ

7h 20m

1 stop

3:20 pm - 7:39 am

MBJ

ORD

16h 19m

1 stop

$366American Airlines

Thu, Apr 16 - Tue, Apr 21

7:20 pm - 1:27 pm

MDW

MBJ

18h 07m

1 stop

4:32 pm - 8:47 am

MBJ

MDW

16h 15m

2 stops

$367Delta

Mon, Apr 6 - Thu, Apr 23

7:14 pm - 3:28 pm

ORD

MBJ

20h 14m

2 stops

4:32 pm - 10:09 am

MBJ

ORD

17h 37m

2 stops

$367Delta

Tue, Apr 7 - Thu, Apr 23

5:05 am - 11:05 am

ORD

MBJ

6h 00m

1 stop

12:00 pm - 7:51 pm

MBJ

ORD

7h 51m

1 stop

$368Spirit Airlines

Wed, Apr 1 - Thu, Apr 9

8:16 pm - 12:02 pm

ORD

MBJ

14h 46m

1 stop

1:00 pm - 11:22 am

MBJ

ORD

23h 22m

1 stop

$369Spirit Airlines

Fri, Feb 27 - Mon, Mar 2

9:55 am - 1:45 pm

MDW

MBJ

3h 50mnonstop

2:55 pm - 10:20 pm

MBJ

MDW

7h 25m

1 stop

$372Southwest

Sat, Apr 18 - Thu, Apr 23

9:55 am - 1:45 pm

MDW

MBJ

3h 50mnonstop

2:25 pm - 11:40 pm

MBJ

MDW

9h 15m

1 stop

$374Southwest

Sat, May 9 - Fri, May 15

6:55 am - 2:17 pm

MDW

MBJ

7h 22m

1 stop

9:01 am - 8:07 pm

MBJ

MDW

11h 06m

1 stop

$382Frontier

Sat, Mar 14 - Sat, Apr 11

Spirit Airlines flights from Chicago to Montego Bay

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

Spirit Airlines

Mar 3

ORD12:44 pmChicago O'Hare Intl

22h 18m

3 stops

MBJ12:02 pmMontego Bay Sangster Intl

Mar 10

MBJ11:57 amMontego Bay Sangster Intl

7h 14m

1 stop

ORD7:11 pmChicago O'Hare Intl

$364

Spirit Airlines

Apr 1

ORD5:05 amChicago O'Hare Intl

6h 00m

1 stop

MBJ11:05 amMontego Bay Sangster Intl

Apr 8

MBJ12:00 pmMontego Bay Sangster Intl

7h 51m

1 stop

ORD7:51 pmChicago O'Hare Intl

$368

Spirit Airlines

Feb 27

ORD8:16 pmChicago O'Hare Intl

14h 46m

1 stop

MBJ12:02 pmMontego Bay Sangster Intl

Mar 2

MBJ1:00 pmMontego Bay Sangster Intl

23h 22m

1 stop

ORD11:22 amChicago O'Hare Intl

$369

Air Canada flights from Chicago to Montego Bay

Our best Air Canada deals on Chicago to Montego Bay flight tickets

Air Canada

May 10

ORD8:20 pmChicago O'Hare Intl

15h 00m

1 stop

MBJ11:20 amMontego Bay Sangster Intl

May 17

MBJ12:15 pmMontego Bay Sangster Intl

24h 02m

2 stops

ORD12:17 pmChicago O'Hare Intl

$397

Air Canada

May 12

ORD6:03 pmChicago O'Hare Intl

17h 17m

2 stops

MBJ11:20 amMontego Bay Sangster Intl

May 17

MBJ12:15 pmMontego Bay Sangster Intl

24h 02m

2 stops

ORD12:17 pmChicago O'Hare Intl

$406

Air Canada

Feb 22

ORD7:15 amChicago O'Hare Intl

9h 50m

1 stop

MBJ6:05 pmMontego Bay Sangster Intl

Mar 1

MBJ7:05 pmMontego Bay Sangster Intl

24h 47m

2 stops

ORD6:52 pmChicago O'Hare Intl

$464

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/3

12:44 pm-12:02 pm

3 stops22h 18m

Montego Bay Sangster Intl

Tue 3/10

11:57 am-7:11 pm

1 stop7h 14m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/16

5:00 am-1:25 pm

1 stop8h 25m

Montego Bay Sangster Intl

Mon 4/20

4:37 pm-2:39 pm

1 stop22h 02m

$365

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/16

6:05 am-1:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Tue 4/21

3:20 pm-7:39 am

1 stop16h 19m

$366

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 4/6

7:20 pm-1:27 pm

1 stop18h 07m

Montego Bay Sangster Intl

Thu 4/23

4:32 pm-8:47 am

2 stops16h 15m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/7

7:14 pm-3:28 pm

2 stops20h 14m

Montego Bay Sangster Intl

Thu 4/23

4:32 pm-10:09 am

2 stops17h 37m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 4/1

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

Thu 4/9

12:00 pm-7:51 pm

1 stop7h 51m

$368

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/27

8:16 pm-12:02 pm

1 stop14h 46m

Montego Bay Sangster Intl

Mon 3/2

1:00 pm-11:22 am

1 stop23h 22m

$369

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/18

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Thu 4/23

2:55 pm-10:20 pm

1 stop7h 25m

$372

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 5/9

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Fri 5/15

2:25 pm-11:40 pm

1 stop9h 15m

$374

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 3/14

6:55 am-2:17 pm

1 stop7h 22m

Montego Bay Sangster Intl

Sat 4/11

9:01 am-8:07 pm

1 stop11h 06m

$382

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

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 $546. 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 $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 10% 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	$224
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 $224. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $484.

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 57.77% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 36.13%, Airbus A321-100/200 at 2.27%, and Boeing 737-900 at 1.57%.
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 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 $130	Free Cancellation	Rating 6.3 8,444 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $144	Free Cancellation	Rating 5.7 3,052 reviews	Search Frontier flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 8,181 reviews	Search Delta flights
United Airlines	PriceFrom $356	Free Cancellation	Rating 7.4 9,279 reviews	Search United Airlines flights
American Airlines	PriceFrom $412	Free Cancellation	Rating 7.2 11,271 reviews	Search American Airlines flights
Southwest	PriceFrom $518	Free Cancellation	Rating 8.0 4,280 reviews	Search Southwest flights

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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.

An easier way to manage your Montego Bay trip

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Cheap flights from Chicago to Montego Bay from $111

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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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?

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

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

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Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Montego Bay

List of cabin classes available on flights landing in Montego Bay. Availability may vary depending on flight origin and airline.

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