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 Southwest 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 69% 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 Atlanta (ATL) offer the lowest average round-trip price of $446.

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 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.

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

Delta and JetBlue 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 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.

$163 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 $425 to $662. The lowest price recently found on this route was $391.

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.

7:00 am - 1:48 pm

ORD

MBJ

6h 48m

1 stop

3:59 pm - 11:44 pm

MBJ

ORD

8h 45m

1 stop

$391JetBlue

Fri, Oct 30 - Tue, Nov 3

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

3:59 pm - 11:44 pm

MBJ

ORD

8h 45m

1 stop

$394JetBlue

Mon, Nov 2 - Wed, Nov 11

9:38 pm - 1:30 pm

ORD

MBJ

15h 52m

1 stop

12:52 pm - 11:21 pm

MBJ

ORD

10h 29m

1 stop

$407United Airlines

Fri, Oct 16 - Mon, Oct 19

5:30 am - 1:30 pm

ORD

MBJ

8h 00m

1 stop

2:45 pm - 12:34 am

MBJ

ORD

9h 49m

1 stop

$410United Airlines

Sun, Oct 18 - Sun, Oct 25

5:30 am - 12:07 pm

ORD

MBJ

6h 37m

1 stop

1:32 pm - 11:51 pm

MBJ

ORD

10h 19m

1 stop

$414Delta

Fri, Oct 23 - Mon, Oct 26

7:00 am - 1:40 pm

ORD

MBJ

5h 40m

1 stop

5:00 pm - 11:44 pm

MBJ

ORD

7h 44m

1 stop

$418JetBlue

Sat, Dec 5 - Sat, Dec 12

5:00 am - 12:50 pm

MDW

MBJ

7h 50m

1 stop

2:15 pm - 10:20 pm

MBJ

MDW

8h 05m

2 stops

$421Southwest

Sat, Aug 22 - Fri, Aug 28

5:05 am - 2:25 pm

MDW

MBJ

8h 20m

1 stop

1:00 pm - 7:00 pm

MBJ

MDW

7h 00m

1 stop

$459Southwest

Sun, Dec 6 - Wed, Dec 9

6:05 am - 12:27 pm

MDW

MBJ

6h 22m

1 stop

1:32 pm - 10:03 pm

MBJ

MDW

8h 31m

1 stop

$472Frontier

Tue, Aug 11 - Sat, Aug 15

6:05 am - 12:24 pm

MDW

MBJ

6h 19m

1 stop

1:32 pm - 10:03 pm

MBJ

MDW

8h 31m

1 stop

$482Frontier

Sun, Aug 2 - Thu, Aug 6

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JetBlue flights from Chicago to Montego Bay

Our best JetBlue deals on Chicago to Montego Bay flight tickets

JetBlue

Oct 30

ORD7:00 amChicago O'Hare Intl

6h 48m

1 stop

MBJ1:48 pmMontego Bay Sangster Intl

Nov 3

MBJ3:59 pmMontego Bay Sangster Intl

8h 45m

1 stop

ORD11:44 pmChicago O'Hare Intl

$391

JetBlue

Nov 2

ORD7:00 amChicago O'Hare Intl

6h 54m

1 stop

MBJ2:54 pmMontego Bay Sangster Intl

Nov 11

MBJ3:59 pmMontego Bay Sangster Intl

8h 45m

1 stop

ORD11:44 pmChicago O'Hare Intl

$394

JetBlue

Dec 5

ORD7:00 amChicago O'Hare Intl

5h 40m

1 stop

MBJ1:40 pmMontego Bay Sangster Intl

Dec 12

MBJ5:00 pmMontego Bay Sangster Intl

7h 44m

1 stop

ORD11:44 pmChicago O'Hare Intl

$418

Frontier flights from Chicago to Montego Bay

Our best Frontier deals on Chicago to Montego Bay flight tickets

Frontier

Aug 11

MDW6:05 amChicago Midway

6h 22m

1 stop

MBJ12:27 pmMontego Bay Sangster Intl

Aug 15

MBJ1:32 pmMontego Bay Sangster Intl

8h 31m

1 stop

MDW10:03 pmChicago Midway

$472

Frontier

Aug 2

MDW6:05 amChicago Midway

6h 19m

1 stop

MBJ12:24 pmMontego Bay Sangster Intl

Aug 6

MBJ1:32 pmMontego Bay Sangster Intl

8h 31m

1 stop

MDW10:03 pmChicago Midway

$482

Frontier

Sep 9

MDW12:03 pmChicago Midway

25h 28m

1 stop

MBJ1:31 pmMontego Bay Sangster Intl

Sep 13

MBJ2:49 pmMontego Bay Sangster Intl

7h 09m

1 stop

MDW9:58 pmChicago Midway

$491

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/30

7:00 am-1:48 pm

1 stop6h 48m

Montego Bay Sangster Intl

Tue 11/3

3:59 pm-11:44 pm

1 stop8h 45m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 11/2

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Wed 11/11

3:59 pm-11:44 pm

1 stop8h 45m

$394

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/16

9:38 pm-1:30 pm

1 stop15h 52m

Montego Bay Sangster Intl

Mon 10/19

12:52 pm-11:21 pm

1 stop10h 29m

$407

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 10/18

5:30 am-1:30 pm

1 stop8h 00m

Montego Bay Sangster Intl

Sun 10/25

2:45 pm-12:34 am

1 stop9h 49m

$410

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/23

5:30 am-12:07 pm

1 stop6h 37m

Montego Bay Sangster Intl

Mon 10/26

1:32 pm-11:51 pm

1 stop10h 19m

$414

Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 12/5

7:00 am-1:40 pm

1 stop5h 40m

Montego Bay Sangster Intl

Sat 12/12

5:00 pm-11:44 pm

1 stop7h 44m

$418

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/22

5:00 am-12:50 pm

1 stop7h 50m

Montego Bay Sangster Intl

Fri 8/28

2:15 pm-10:20 pm

2 stops8h 05m

$421

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 12/6

5:05 am-2:25 pm

1 stop8h 20m

Montego Bay Sangster Intl

Wed 12/9

1:00 pm-7:00 pm

1 stop7h 00m

$459

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 8/11

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Sat 8/15

1:32 pm-10:03 pm

1 stop8h 31m

$472

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/2

6:05 am-12:24 pm

1 stop6h 19m

Montego Bay Sangster Intl

Thu 8/6

1:32 pm-10:03 pm

1 stop8h 31m

$482

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 August, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $127.

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 $491. 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 $620.

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 $527 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 $468 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	$284
Fastest flight time	4h 04m
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 $284. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $597.

The fastest flight from Chicago to Montego Bay takes 4h 04m

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 4h 04m.
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 75.98% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.73%, Boeing 737 at 6.16%, and Airbus A321-100/200 at 3.08%.
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 2,823 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.8 8,458 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 3,010 reviews	Search JetBlue flights
United Airlines	PriceFrom $297	Free Cancellation	Rating 7.4 9,979 reviews	Search United Airlines flights
American Airlines	PriceFrom $318	Free Cancellation	Rating 7.1 11,806 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 7.9 4,251 reviews	Search Southwest flights

United Airlines Flights From Chicago to Montego Bay
United Airlines flight deals from Chicago to Montego Bay start from $297 round-trip. Over the 1 United Airlines flight for this route in a normal week, average airfare is usually $527 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 $318 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $539. American Airlines operates 7 flights to Montego Bay from Chicago in an average week. Users have rated it 7.1/10 across 11,804 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 $163

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 8/29. 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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JetBlue flights from Chicago to Montego Bay

Our best JetBlue deals on Chicago to Montego Bay flight tickets

Frontier flights from Chicago to Montego Bay

Our best Frontier 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

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

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

United Airlines Flights From Chicago to Montego Bay

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

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