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.

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.

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

As of July 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 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.

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.

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

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

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 connection time from Chicago to Montego Bay?

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

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

Fri, Jan 22 - Fri, Jan 29

8:40 am - 1:48 pm

ORD

MBJ

4h 08mnonstop

2:54 pm - 6:20 pm

MBJ

ORD

4h 26mnonstop

$428United Airlines

Wed, Nov 4 - Wed, Nov 11

8:05 am - 1:19 pm

ORD

MBJ

4h 14mnonstop

3:17 pm - 6:56 pm

MBJ

ORD

4h 39mnonstop

$428American Airlines

Sun, Jan 24 - Fri, Feb 5

8:05 am - 1:19 pm

ORD

MBJ

4h 14mnonstop

3:17 pm - 6:56 pm

MBJ

ORD

4h 39mnonstop

$428American Airlines

Tue, Jan 26 - Tue, Feb 9

5:55 am - 12:25 pm

MDW

MBJ

6h 30m

1 stop

11:40 am - 8:35 pm

MBJ

MDW

8h 55m

1 stop

$442Southwest

Sat, Sep 12 - Sat, Sep 19

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

Tue, Sep 22 - Tue, Sep 29

6:00 am - 4:35 pm

MDW

MBJ

9h 35m

1 stop

2:20 pm - 10:56 pm

MBJ

MDW

9h 36m

1 stop

$442Delta

Fri, Dec 4 - Mon, Dec 7

6:00 am - 4:35 pm

MDW

MBJ

9h 35m

1 stop

3:40 pm - 10:56 pm

MBJ

MDW

8h 16m

1 stop

$442Delta

Sun, Dec 6 - Thu, Dec 10

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

Wed, Oct 28 - Sun, 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

Thu, Dec 10 - Sun, Dec 13

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Air Canada flights from Chicago to Montego Bay

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

Air Canada

Oct 28

ORD9:05 pmChicago O'Hare Intl

14h 45m

1 stop

MBJ11:50 amMontego Bay Sangster Intl

Nov 1

MBJ2:20 pmMontego Bay Sangster Intl

25h 32m

1 stop

ORD2:52 pmChicago O'Hare Intl

$450

Air Canada

Oct 28

ORD3:45 pmChicago O'Hare Intl

20h 05m

2 stops

MBJ11:50 amMontego Bay Sangster Intl

Nov 1

MBJ2:20 pmMontego Bay Sangster Intl

25h 32m

1 stop

ORD2:52 pmChicago O'Hare Intl

$453

Air Canada

Nov 21

ORD3:45 pmChicago O'Hare Intl

20h 40m

1 stop

MBJ1:25 pmMontego Bay Sangster Intl

Nov 28

MBJ6:20 pmMontego Bay Sangster Intl

16h 03m

1 stop

ORD9:23 amChicago O'Hare Intl

$455

American Airlines flights from Chicago to Montego Bay

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

American Airlines

Sep 12

ORD8:15 amChicago O'Hare Intl

8h 01m

1 stop

MBJ4:16 pmMontego Bay Sangster Intl

Sep 19

MBJ5:16 pmMontego Bay Sangster Intl

7h 17m

1 stop

ORD12:33 amChicago O'Hare Intl

$433

American Airlines

Oct 28

ORD6:59 amChicago O'Hare Intl

9h 13m

1 stop

MBJ4:12 pmMontego Bay Sangster Intl

Nov 18

MBJ3:57 pmMontego Bay Sangster Intl

4h 49m

ORD7:46 pmChicago O'Hare Intl

$437

American Airlines

Nov 3

ORD9:40 amChicago O'Hare Intl

4h 17m

MBJ2:57 pmMontego Bay Sangster Intl

Nov 10

MBJ6:09 pmMontego Bay Sangster Intl

7h 35m

1 stop

ORD12:44 amChicago O'Hare Intl

$438

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/22

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Fri 1/29

2:48 pm-6:16 pm

Nonstop4h 28m

$428

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/4

8:40 am-1:48 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Wed 11/11

2:54 pm-6:20 pm

Nonstop4h 26m

$428

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/24

8:05 am-1:19 pm

Nonstop4h 14m

Montego Bay Sangster Intl

Fri 2/5

3:17 pm-6:56 pm

Nonstop4h 39m

$428

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/26

8:05 am-1:19 pm

Nonstop4h 14m

Montego Bay Sangster Intl

Tue 2/9

3:17 pm-6:56 pm

Nonstop4h 39m

$428

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/12

5:55 am-12:25 pm

1 stop6h 30m

Montego Bay Sangster Intl

Sat 9/19

11:40 am-8:35 pm

1 stop8h 55m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/22

6:30 am-12:55 pm

1 stop6h 25m

Montego Bay Sangster Intl

Tue 9/29

12:55 pm-9:25 pm

1 stop8h 30m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 12/4

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Mon 12/7

2:20 pm-10:56 pm

1 stop9h 36m

$442

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 12/6

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Thu 12/10

3:40 pm-10:56 pm

1 stop8h 16m

$442

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 10/28

9:05 pm-11:50 am

1 stop14h 45m

Montego Bay Sangster Intl

Sun 11/1

2:20 pm-2:52 pm

1 stop25h 32m

$450

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 12/10

3:45 pm-1:25 pm

1 stop20h 40m

Montego Bay Sangster Intl

Sun 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 2,747 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.8 8,487 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 3,028 reviews	Search JetBlue flights
United Airlines	PriceFrom $302	Free Cancellation	Rating 7.4 10,051 reviews	Search United Airlines flights
American Airlines	PriceFrom $317	Free Cancellation	Rating 7.1 11,842 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 8.0 4,226 reviews	Search Southwest flights

American Airlines Flights From Chicago to Montego Bay
American Airlines flight deals from Chicago to Montego Bay start from $317 round-trip. Over the 7 American Airlines flights for this route in a normal week, average airfare is usually $542 round-trip - but some users have found much cheaper deals with momondo.

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 10/27. 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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Air Canada flights from Chicago to Montego Bay

Our best Air Canada 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

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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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