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

Flights via Atlanta (ATL) offer the lowest average round-trip price of $374.

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

As of March 2026, there are 2 flights per day flying from Chicago to Montego Bay. The most common time of day flights depart is 8:00AM, with 100% of flights taking off at noon.

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

As of March 2026, there are 16 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Sat, with 19% 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: 1h 15m.

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 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.

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.

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

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

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

Fort Lauderdale (FLL) was the most common stop: 40% 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 March 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.

$125 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 $446 to $702. The lowest price recently found on this route was $302.

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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.

5:05 am - 12:16 pm

ORD

MBJ

7h 11m

1 stop

1:16 pm - 7:55 am

MBJ

ORD

18h 39m

1 stop

$302Multiple Airlines

Sun, May 3 - Sat, May 9

8:05 am - 12:13 pm

ORD

MBJ

4h 08mnonstop

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

$318American Airlines

Mon, May 4 - Fri, May 8

12:27 pm - 12:11 pm

MDW

MBJ

23h 44m

1 stop

1:16 pm - 2:12 pm

MBJ

MDW

24h 56m

2 stops

$323Frontier

Tue, May 5 - Tue, May 12

4:28 pm - 12:11 pm

ORD

MBJ

19h 43m

1 stop

1:16 pm - 11:13 pm

MBJ

ORD

33h 57m

2 stops

$324Frontier

Mon, May 4 - Tue, May 12

5:05 am - 11:05 am

ORD

MBJ

6h 00m

1 stop

1:21 pm - 12:24 am

MBJ

ORD

11h 03m

1 stop

$326Spirit Airlines

Tue, Apr 14 - Tue, Apr 28

8:40 am - 12:50 pm

ORD

MBJ

4h 10mnonstop

4:12 pm - 11:43 pm

MBJ

ORD

7h 31m

1 stop

$328United Airlines

Sun, Apr 26 - Wed, Apr 29

5:05 am - 12:16 pm

ORD

MBJ

7h 11m

1 stop

1:21 pm - 12:27 am

MBJ

ORD

11h 06m

1 stop

$330Spirit Airlines

Tue, Apr 28 - Thu, May 14

8:45 am - 3:10 pm

ORD

MBJ

6h 25m

1 stop

2:40 pm - 12:45 am

MBJ

ORD

10h 05m

1 stop

$332United Airlines

Mon, May 4 - Fri, May 8

7:00 am - 1:55 pm

MDW

MBJ

6h 55m

1 stop

11:35 am - 8:40 pm

MBJ

MDW

9h 05m

1 stop

$332Southwest

Tue, Apr 28 - Sat, May 2

5:15 am - 2:20 pm

MDW

MBJ

9h 05m

1 stop

2:30 pm - 6:35 pm

MBJ

MDW

4h 05mnonstop

$357Southwest

Sun, May 31 - Sat, Jun 6

Spirit Airlines flights from Chicago to Montego Bay

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

Spirit Airlines

Apr 12

ORD6:10 pmChicago O'Hare Intl

16h 55m

1 stop

MBJ11:05 amMontego Bay Sangster Intl

Apr 16

MBJ1:21 pmMontego Bay Sangster Intl

11h 03m

1 stop

ORD12:24 amChicago O'Hare Intl

$321

Spirit Airlines

Apr 14

ORD5:05 amChicago O'Hare Intl

6h 00m

1 stop

MBJ11:05 amMontego Bay Sangster Intl

Apr 28

MBJ1:21 pmMontego Bay Sangster Intl

11h 03m

1 stop

ORD12:24 amChicago O'Hare Intl

$326

Spirit Airlines

Apr 28

ORD5:05 amChicago O'Hare Intl

7h 11m

1 stop

MBJ12:16 pmMontego Bay Sangster Intl

May 14

MBJ1:21 pmMontego Bay Sangster Intl

11h 06m

1 stop

ORD12:27 amChicago O'Hare Intl

$330

Southwest flights from Chicago to Montego Bay

Our best Southwest deals on Chicago to Montego Bay flight tickets

Southwest

Apr 28

MDW7:00 amChicago Midway

6h 55m

1 stop

MBJ1:55 pmMontego Bay Sangster Intl

May 2

MBJ11:35 amMontego Bay Sangster Intl

9h 05m

1 stop

MDW8:40 pmChicago Midway

$332

Southwest

May 31

MDW5:15 amChicago Midway

9h 05m

1 stop

MBJ2:20 pmMontego Bay Sangster Intl

Jun 6

MBJ2:30 pmMontego Bay Sangster Intl

4h 05m

MDW6:35 pmChicago Midway

$357

Southwest

Apr 14

MDW7:00 amChicago Midway

6h 55m

1 stop

MBJ1:55 pmMontego Bay Sangster Intl

May 14

MBJ12:35 pmMontego Bay Sangster Intl

9h 45m

1 stop

MDW10:20 pmChicago Midway

$394

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 5/3

5:05 am-12:16 pm

1 stop7h 11m

Montego Bay Sangster Intl

Sat 5/9

1:16 pm-7:55 am

1 stop18h 39m

$302

Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Fri 5/8

1:15 pm-5:55 pm

Nonstop4h 40m

$318

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 5/5

12:27 pm-12:11 pm

1 stop23h 44m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-2:12 pm

2 stops24h 56m

$323

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

4:28 pm-12:11 pm

1 stop19h 43m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-11:13 pm

2 stops33h 57m

$324

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/14

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

Tue 4/28

1:21 pm-12:24 am

1 stop11h 03m

$326

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/26

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Wed 4/29

4:12 pm-11:43 pm

1 stop7h 31m

$328

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/28

5:05 am-12:16 pm

1 stop7h 11m

Montego Bay Sangster Intl

Thu 5/14

1:21 pm-12:27 am

1 stop11h 06m

$330

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

8:45 am-3:10 pm

1 stop6h 25m

Montego Bay Sangster Intl

Fri 5/8

2:40 pm-12:45 am

1 stop10h 05m

$332

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 4/28

7:00 am-1:55 pm

1 stop6h 55m

Montego Bay Sangster Intl

Sat 5/2

11:35 am-8:40 pm

1 stop9h 05m

$332

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/31

5:15 am-2:20 pm

1 stop9h 05m

Montego Bay Sangster Intl

Sat 6/6

2:30 pm-6:35 pm

Nonstop4h 05m

$357

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 April is also cheap. Prices for this month can be found on momondo for an average of $531.

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 $507. 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 $660.

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 $551 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 $505 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 21% 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 March 2026, prices for Chicago to Montego Bay flights are approximately 42% 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	$182
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 $182. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $298.

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 March 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 64.19% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 32.16%, Airbus A321-100/200 at 1.43%, and Boeing 737-900 at 1.04%.
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 $141	Free Cancellation	Rating 6.3 8,532 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $144	Free Cancellation	Rating 5.7 3,019 reviews	Search Frontier flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 8,314 reviews	Search Delta flights
United Airlines	PriceFrom $302	Free Cancellation	Rating 7.4 9,455 reviews	Search United Airlines flights
American Airlines	PriceFrom $375	Free Cancellation	Rating 7.1 11,486 reviews	Search American Airlines flights
Southwest	PriceFrom $518	Free Cancellation	Rating 8.0 4,324 reviews	Search Southwest flights

Southwest Flights From Chicago to Montego Bay
Southwest flight deals from Chicago to Montego Bay start from $518 round-trip. Over the 2 Southwest flights for this route in a normal week, average airfare is usually $683 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Chicago to Montego Bay
United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago to Montego Bay start from as low as $302 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $547. United Airlines operates 7 flights to Montego Bay from Chicago in an average week. Users have rated it 7.4/10 across 9,455 reviews.

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

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Cheap flights from Chicago to Montego Bay from $125

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 5/4. 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?

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

Best airlines flying from Chicago to Montego Bay

Compare and see reviews for airlines that fly from Chicago to Montego Bay with momondo

Southwest Flights From Chicago to Montego Bay

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An easier way to manage your Montego Bay trip

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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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