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 68% of people opting to fly with this airline when traveling to Montego Bay. Keep in mind that there are 7 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 Charlotte (CLT) offer the lowest average round-trip price of $384.

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

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

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

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

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

Charlotte (CLT) has the shortest average layover time for this route: 1h 27m.

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

As of May 2026, there are 9 flights per week flying from Chicago to Montego Bay. The most common day of the week flights depart is Sat, with 33% of flights taking off on this day.

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

As of May 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.

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 7 as of May 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.

$128 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 $696 to $464. The lowest price recently found on this route was $330.

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Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

2:00 pm - 11:44 pm

MBJ

ORD

10h 44m

1 stop

$330JetBlue

mar., nov. 3 - mar., nov. 10

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

2:00 pm - 11:44 pm

MBJ

ORD

10h 44m

1 stop

$331JetBlue

lun., nov. 9 - vie., nov. 13

9:45 am - 3:01 pm

ORD

MBJ

4h 16mnonstop

2:19 pm - 6:00 pm

MBJ

ORD

4h 41mnonstop

$338American Airlines

mar., nov. 3 - mar., nov. 10

7:50 am - 11:45 am

MDW

MBJ

3h 55mnonstop

2:30 pm - 6:35 pm

MBJ

MDW

4h 05mnonstop

$338Southwest

dom., jun. 28 - sáb., jul. 4

5:18 am - 2:59 pm

ORD

MBJ

8h 41m

1 stop

2:19 pm - 6:00 pm

MBJ

ORD

4h 41mnonstop

$342American Airlines

mar., nov. 3 - mar., nov. 10

9:45 am - 3:01 pm

ORD

MBJ

4h 16mnonstop

3:14 pm - 6:55 pm

MBJ

ORD

4h 41mnonstop

$343American Airlines

sáb., nov. 7 - dom., nov. 15

7:00 am - 2:54 pm

ORD

MBJ

6h 54m

1 stop

3:59 pm - 11:44 pm

MBJ

ORD

8h 45m

1 stop

$346JetBlue

mar., nov. 3 - mar., nov. 10

5:05 am - 12:35 pm

MDW

MBJ

7h 30m

1 stop

2:30 pm - 6:35 pm

MBJ

MDW

4h 05mnonstop

$447Southwest

dom., jun. 28 - sáb., jul. 4

6:05 am - 3:34 pm

MDW

MBJ

9h 29m

1 stop

1:09 pm - 10:36 pm

MBJ

MDW

9h 27m

1 stop

$452Delta

dom., ago. 16 - jue., ago. 20

6:05 am - 1:01 pm

MDW

MBJ

6h 56m

1 stop

4:59 pm - 9:17 am

MBJ

MDW

16h 18m

2 stops

$457Delta

sáb., ago. 15 - mié., ago. 26

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 11/3

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

mar. 11/10

2:00 pm-11:44 pm

1 stop10h 44m

$330

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 11/9

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

vie. 11/13

2:00 pm-11:44 pm

1 stop10h 44m

$331

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 11/3

9:45 am-3:01 pm

Nonstop4h 16m

Montego Bay Sangster Intl

mar. 11/10

2:19 pm-6:00 pm

Nonstop4h 41m

$338

Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 6/28

7:50 am-11:45 am

Nonstop3h 55m

Montego Bay Sangster Intl

sáb. 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

$338

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 11/3

5:18 am-2:59 pm

1 stop8h 41m

Montego Bay Sangster Intl

mar. 11/10

2:19 pm-6:00 pm

Nonstop4h 41m

$342

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 11/7

9:45 am-3:01 pm

Nonstop4h 16m

Montego Bay Sangster Intl

dom. 11/15

3:14 pm-6:55 pm

Nonstop4h 41m

$343

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 11/3

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

mar. 11/10

3:59 pm-11:44 pm

1 stop8h 45m

$346

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 6/28

5:05 am-12:35 pm

1 stop7h 30m

Montego Bay Sangster Intl

sáb. 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

$447

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 8/16

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

jue. 8/20

1:09 pm-10:36 pm

1 stop9h 27m

$452

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 8/15

6:05 am-1:01 pm

1 stop6h 56m

Montego Bay Sangster Intl

mié. 8/26

4:59 pm-9:17 am

2 stops16h 18m

$457

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 June is also cheap. Prices for this month can be found on momondo for an average of $119.

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 $494. 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 $640.

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 $530 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 $465 on momondo.

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

There are 2 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?

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 May 2026, prices for Chicago to Montego Bay flights are approximately 11% 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

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 50m.
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 7 as of May 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 72.80% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 19.55%, Airbus A321-100/200 at 4.25%, and Boeing 737 at 1.98%.
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 22%, Southwest with 8%, and Spirit Airlines with 5%.

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 $118	Free Cancellation	Rating 6.2	Search Spirit Airlines flights
Frontier	PriceFrom $144	Free Cancellation	Rating 5.6 2,936 reviews	Search Frontier flights
Delta	PriceFrom $178	Free Cancellation	Rating 7.9 8,428 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 2,979 reviews	Search JetBlue flights
United Airlines	PriceFrom $302	Free Cancellation	Rating 7.4 9,749 reviews	Search United Airlines flights
American Airlines	PriceFrom $319	Free Cancellation	Rating 7.1 11,630 reviews	Search American Airlines flights
Southwest	PriceFrom $468	Free Cancellation	Rating 7.9 4,266 reviews	Search Southwest flights

Southwest Flights From Chicago to Montego Bay
Southwest flight deals from Chicago to Montego Bay start from $468 round-trip. Over the 1 Southwest flight for this route in a normal week, average airfare is usually $646 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 $519. United Airlines operates 1 flight to Montego Bay from Chicago in an average week. Users have rated it 7.4/10 across 9,749 reviews.

Lucea

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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 $128

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 8/17. 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 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

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

Southwest Flights From Chicago to Montego Bay

United 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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Airports servicing Jamaica

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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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