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

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

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

As of July 2026, there are 8 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Sat, with 25% of flights taking off on this day.

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

Orlando (MCO) has the shortest average layover time for this route: 2h 23m.

What airlines fly to Montego Bay?

American Airlines, United Airlines and Delta 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.

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

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

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

Flights via Atlanta (ATL) offer the lowest average round-trip price of $446.

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

As of July 2026, there are 1 flights per day flying from Chicago to Montego Bay. The most common time of day flights depart is 9:00AM, with 100% of flights taking off at noon.

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 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 July 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.

$193 Cheap Flights from Chicago to Montego Bay in 2026

Discover deals from 900+ travel sites with momondo.

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.

8:42 am - 1:46 pm

ORD

MBJ

4h 04mnonstop

2:48 pm - 6:16 pm

MBJ

ORD

4h 28mnonstop

$428United Airlines

Fr, Jän 8 - Di, Jän 12

8:42 am - 1:46 pm

ORD

MBJ

4h 04mnonstop

2:48 pm - 6:16 pm

MBJ

ORD

4h 28mnonstop

$428United Airlines

Mi, Dez 2 - Mi, Dez 9

8:05 am - 1:19 pm

ORD

MBJ

4h 14mnonstop

3:17 pm - 6:56 pm

MBJ

ORD

4h 39mnonstop

$428American Airlines

So, Jän 24 - Fr, Feb 5

8:05 am - 1:19 pm

ORD

MBJ

4h 14mnonstop

3:17 pm - 6:56 pm

MBJ

ORD

4h 39mnonstop

$428American Airlines

So, Jän 24 - Do, Jän 28

6:30 am - 12:55 pm

MDW

MBJ

6h 25m

1 stop

12:55 pm - 9:25 pm

MBJ

MDW

8h 30m

1 stop

$442Southwest

Di, Sep 22 - Di, Sep 29

6:05 am - 2:25 pm

MDW

MBJ

7h 20m

1 stop

3:25 pm - 11:05 pm

MBJ

MDW

8h 40m

1 stop

$442Southwest

Fr, Dez 4 - Fr, Dez 11

9:50 am - 3:34 pm

ORD

MBJ

5h 44m

1 stop

1:32 pm - 9:00 pm

MBJ

ORD

7h 28m

1 stop

$442Delta

Fr, Okt 23 - Mi, Okt 28

5:55 pm - 11:30 am

ORD

MBJ

17h 35m

1 stop

2:16 pm - 11:52 pm

MBJ

ORD

10h 36m

1 stop

$442Delta

Di, Okt 27 - Mo, Nov 2

9:05 pm - 11:50 am

ORD

MBJ

14h 45m

1 stop

2:20 pm - 2:52 pm

MBJ

ORD

25h 32m

1 stop

$450Air Canada

Mi, Okt 28 - So, Nov 1

3:45 pm - 1:25 pm

ORD

MBJ

20h 40m

1 stop

2:20 pm - 2:52 pm

MBJ

ORD

25h 32m

1 stop

$450Air Canada

Do, Dez 10 - So, Dez 13

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United Airlines flights from Chicago to Montego Bay

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

United Airlines

Dec 2

ORD8:42 amChicago O'Hare Intl

4h 04m

MBJ1:46 pmMontego Bay Sangster Intl

Dec 9

MBJ3:36 pmMontego Bay Sangster Intl

9h 06m

1 stop

ORD11:42 pmChicago O'Hare Intl

$434

United Airlines

Dec 7

ORD8:42 amChicago O'Hare Intl

4h 04m

MBJ1:46 pmMontego Bay Sangster Intl

Dec 12

MBJ3:36 pmMontego Bay Sangster Intl

9h 06m

1 stop

ORD11:42 pmChicago O'Hare Intl

$436

United Airlines

Dec 7

ORD5:00 amChicago O'Hare Intl

8h 29m

1 stop

MBJ2:29 pmMontego Bay Sangster Intl

Dec 12

MBJ3:36 pmMontego Bay Sangster Intl

9h 06m

1 stop

ORD11:42 pmChicago O'Hare Intl

$440

Southwest flights from Chicago to Montego Bay

Our best Southwest deals on Chicago to Montego Bay flight tickets

Southwest

Dec 4

MDW6:05 amChicago Midway

7h 20m

1 stop

MBJ2:25 pmMontego Bay Sangster Intl

Dec 11

MBJ3:25 pmMontego Bay Sangster Intl

8h 40m

1 stop

MDW11:05 pmChicago Midway

$442

Southwest

Sep 19

MDW5:55 amChicago Midway

6h 30m

1 stop

MBJ12:25 pmMontego Bay Sangster Intl

Sep 23

MBJ12:55 pmMontego Bay Sangster Intl

8h 10m

1 stop

MDW9:05 pmChicago Midway

$450

Southwest

Sep 19

MDW5:55 amChicago Midway

6h 30m

1 stop

MBJ12:25 pmMontego Bay Sangster Intl

Sep 23

MBJ12:55 pmMontego Bay Sangster Intl

9h 30m

2 stops

MDW10:25 pmChicago Midway

$455

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fr 1/8

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Di 1/12

2:48 pm-6:16 pm

Nonstop4h 28m

$428

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mi 12/2

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Mi 12/9

2:48 pm-6:16 pm

Nonstop4h 28m

$428

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

So 1/24

8:05 am-1:19 pm

Nonstop4h 14m

Montego Bay Sangster Intl

Fr 2/5

3:17 pm-6:56 pm

Nonstop4h 39m

$428

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

So 1/24

8:05 am-1:19 pm

Nonstop4h 14m

Montego Bay Sangster Intl

Do 1/28

3:17 pm-6:56 pm

Nonstop4h 39m

$428

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Di 9/22

6:30 am-12:55 pm

1 stop6h 25m

Montego Bay Sangster Intl

Di 9/29

12:55 pm-9:25 pm

1 stop8h 30m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fr 12/4

6:05 am-2:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Fr 12/11

3:25 pm-11:05 pm

1 stop8h 40m

$442

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fr 10/23

9:50 am-3:34 pm

1 stop5h 44m

Montego Bay Sangster Intl

Mi 10/28

1:32 pm-9:00 pm

1 stop7h 28m

$442

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Di 10/27

5:55 pm-11:30 am

1 stop17h 35m

Montego Bay Sangster Intl

Mo 11/2

2:16 pm-11:52 pm

1 stop10h 36m

$442

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mi 10/28

9:05 pm-11:50 am

1 stop14h 45m

Montego Bay Sangster Intl

So 11/1

2:20 pm-2:52 pm

1 stop25h 32m

$450

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Do 12/10

3:45 pm-1:25 pm

1 stop20h 40m

Montego Bay Sangster Intl

So 12/13

2:20 pm-2:52 pm

1 stop25h 32m

$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?

Prices are currently low for flights on this route.

Typical prices usually range from $455 to $640.
The lowest price recently found on this route was $428.

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of April, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $480.

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 $486. 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 $605.

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 from Chicago 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 $526 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 $463 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Montego Bay 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 July 2026, prices for Chicago to Montego Bay flights are approximately 6% 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	$196
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 $196. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $547.

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 in Montego Bay. From Chicago there are direct flights to Montego Bay Sangster Intl (MBJ).

Search flight deals

Frequently asked questions about flying from Chicago to Montego Bay

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 55m.
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 July 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 73.75% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.80%, Boeing 737 at 8.46%, and Airbus A321-100/200 at 1.74%.
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 25%, Southwest with 8%, and Frontier with 4%.

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
Frontier	PriceFrom $144	Free Cancellation	Rating 5.6 2,754 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.8 8,483 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 3,026 reviews	Search JetBlue flights
United Airlines	PriceFrom $302	Free Cancellation	Rating 7.4 10,042 reviews	Search United Airlines flights
American Airlines	PriceFrom $317	Free Cancellation	Rating 7.1 11,837 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 8.0 4,229 reviews	Search Southwest flights

United Airlines Flights From Chicago to Montego Bay
United Airlines flight deals from Chicago to Montego Bay start from $302 round-trip. Over the 1 United Airlines flight for this route in a normal week, average airfare is usually $529 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Chicago to Montego Bay
American Airlines is also a popular choice for this route. American Airlines flight deals for Chicago to Montego Bay start from as low as $317 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $542. American Airlines operates 7 flights to Montego Bay from Chicago in an average week. Users have rated it 7.1/10 across 11,839 reviews.

Falmouth

Lucea

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

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Cheap flights from Chicago to Montego Bay from $193

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 1/22. 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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United Airlines flights from Chicago to Montego Bay

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

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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 from Chicago to Montego Bay?

What cabin class options are available on Chicago to Montego Bay 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

Best Price Found

Fastest flight time

Direct flights

Airports in Montego Bay

Frequently asked questions about flying 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

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.

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

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