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

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 26m.

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.

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 63% 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 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.

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

Spirit Airlines, Frontier, and Southwest 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?

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 18m.

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 September 2025.

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.

$99 Cheap Flights from Chicago to Montego Bay in 2025/26

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Find the cheapest flights from Chicago to Montego Bay

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:42 am - 1:46 pmORD-MBJ

4h 04mnonstop

2:48 pm - 6:13 pmMBJ-ORD

4h 25mnonstop

$376United Airlines

Find Deal

Sat, Nov 8 - Sat, Nov 15

5:05 am - 11:00 amORD-MBJ

5h 55m1 stop

12:09 pm - 11:45 pmMBJ-ORD

11h 36m1 stop

$377Spirit Airlines

Find Deal

Wed, Oct 15 - Sat, Oct 18

8:44 am - 12:45 pmORD-MBJ

4h 01mnonstop

2:05 pm - 7:25 amMBJ-ORD

17h 20m1 stop

$380American Airlines

Find Deal

Tue, Oct 14 - Sat, Oct 18

6:20 am - 3:15 pmMDW-MBJ

8h 55m1 stop

4:30 pm - 6:39 pmMBJ-MDW

27h 09m1 stop

$380Frontier

Find Deal

Thu, Oct 30 - Thu, Nov 6

5:20 am - 1:05 pmORD-MBJ

7h 45m1 stop

2:05 pm - 7:25 amMBJ-ORD

17h 20m1 stop

$385American Airlines

Find Deal

Wed, Oct 15 - Sat, Oct 18

6:00 am - 1:09 pmMDW-MBJ

7h 09m1 stop

1:25 pm - 9:36 pmMBJ-MDW

8h 11m1 stop

$385Delta

Find Deal

Mon, Sep 29 - Thu, Oct 2

1:37 pm - 3:15 pmMDW-MBJ

24h 38m1 stop

4:30 pm - 10:26 amMBJ-MDW

18h 56m2 stops

$388Frontier

Find Deal

Sat, Nov 8 - Sat, Nov 15

6:23 pm - 11:23 amMDW-MBJ

17h 00m2 stops

12:48 pm - 8:40 amMBJ-MDW

19h 52m2 stops

$389Delta

Find Deal

Mon, Oct 20 - Wed, Oct 29

8:45 pm - 2:00 pmMDW-MBJ

17h 15m2 stops

12:55 pm - 8:55 pmMBJ-MDW

8h 00m1 stop

$412Southwest

Find Deal

Mon, Oct 13 - Sat, Oct 18

5:25 am - 12:00 pmMDW-MBJ

6h 35m1 stop

1:00 pm - 10:05 pmMBJ-MDW

9h 05m2 stops

$417Southwest

Find Deal

Wed, Oct 15 - Wed, Oct 22

United Airlines flights from Chicago to Montego Bay

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

United Airlines

Nov 8

ORD8:42 amChicago O'Hare Intl

4h 04m

MBJ1:46 pmMontego Bay Sangster Intl

Nov 15

MBJ2:48 pmMontego Bay Sangster Intl

4h 25m

ORD6:13 pmChicago O'Hare Intl

$376

Find similar

United Airlines

Nov 8

ORD8:48 amChicago O'Hare Intl

6h 24m

1 stop

MBJ4:12 pmMontego Bay Sangster Intl

Nov 15

MBJ2:48 pmMontego Bay Sangster Intl

4h 25m

ORD6:13 pmChicago O'Hare Intl

$381

Find similar

United Airlines

Feb 17

ORD8:42 amChicago O'Hare Intl

4h 04m

MBJ1:46 pmMontego Bay Sangster Intl

Feb 25

MBJ2:48 pmMontego Bay Sangster Intl

4h 25m

ORD6:13 pmChicago O'Hare Intl

$390

Find similar

Air Canada flights from Chicago to Montego Bay

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

Air Canada

Nov 27

ORD9:20 pmChicago O'Hare Intl

19h 45m

2 stops

MBJ6:05 pmMontego Bay Sangster Intl

Dec 1

MBJ5:45 pmMontego Bay Sangster Intl

18h 33m

2 stops

ORD11:18 amChicago O'Hare Intl

$402

Find similar

Air Canada

Nov 20

ORD6:05 pmChicago O'Hare Intl

21h 30m

2 stops

MBJ4:35 pmMontego Bay Sangster Intl

Nov 24

MBJ5:45 pmMontego Bay Sangster Intl

19h 20m

1 stop

ORD12:05 pmChicago O'Hare Intl

$407

Find similar

Air Canada

Oct 7

ORD1:55 pmChicago O'Hare Intl

21h 15m

2 stops

MBJ11:10 amMontego Bay Sangster Intl

Oct 11

MBJ12:10 pmMontego Bay Sangster Intl

20h 59m

1 stop

ORD9:09 amChicago O'Hare Intl

$411

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/8

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 11/15

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 10/15

5:05 am-11:00 am

1 stop5h 55m

Montego Bay Sangster Intl

Sat 10/18

12:09 pm-11:45 pm

1 stop11h 36m

$377

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 10/14

8:44 am-12:45 pm

Nonstop4h 01m

Montego Bay Sangster Intl

Sat 10/18

2:05 pm-7:25 am

1 stop17h 20m

$380

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 10/30

6:20 am-3:15 pm

1 stop8h 55m

Montego Bay Sangster Intl

Thu 11/6

4:30 pm-6:39 pm

1 stop27h 09m

$380

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 10/15

5:20 am-1:05 pm

1 stop7h 45m

Montego Bay Sangster Intl

Sat 10/18

2:05 pm-7:25 am

1 stop17h 20m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 9/29

6:00 am-1:09 pm

1 stop7h 09m

Montego Bay Sangster Intl

Thu 10/2

1:25 pm-9:36 pm

1 stop8h 11m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 11/8

1:37 pm-3:15 pm

1 stop24h 38m

Montego Bay Sangster Intl

Sat 11/15

4:30 pm-10:26 am

2 stops18h 56m

$388

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/20

6:23 pm-11:23 am

2 stops17h 00m

Montego Bay Sangster Intl

Wed 10/29

12:48 pm-8:40 am

2 stops19h 52m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/13

8:45 pm-2:00 pm

2 stops17h 15m

Montego Bay Sangster Intl

Sat 10/18

12:55 pm-8:55 pm

1 stop8h 00m

$412

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 10/15

5:25 am-12:00 pm

1 stop6h 35m

Montego Bay Sangster Intl

Wed 10/22

1:00 pm-10:05 pm

2 stops9h 05m

$417

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

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 February, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $540.

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 Sunday. momondo users have found tickets for Sunday departures for as low as $542. 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 $684.

What is the cheapest time of day to depart on your flight to Montego Bay?

At noon is the cheapest time of day to fly from Chicago to Montego Bay when you can find flight prices for as low as $403. Flying to Montego Bay at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $612.

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 $608 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 $535 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 19% 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 September 2025, prices for Chicago to Montego Bay flights are approximately 20% 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	$201
Fastest flight time	3h 50m
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 $201. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $491.

The fastest flight from Chicago to Montego Bay takes 3h 50m

Direct flights go from Chicago to Montego Bay every day.

There is 1 airport near Montego Bay: 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 59m.
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 September 2025.
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 62.68% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 17.96%, Airbus A321-100/200 at 14.14%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 3.69%.
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 57% of the total bookings. Other popular airlines include United Airlines with 23%, Southwest with 8%, 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 $258	Free Cancellation	Rating 6.3 8,023 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $370	Free Cancellation	Rating 5.8 3,173 reviews	Search Frontier flights
United Airlines	PriceFrom $408	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
American Airlines	PriceFrom $444	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Delta	PriceFrom $448	Free Cancellation	Rating 7.9 7,961 reviews	Search Delta flights
Southwest	PriceFrom $549	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights

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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.

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Cheap flights from Chicago to Montego Bay from $99

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 10/7. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Montego Bay

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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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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

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

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 February, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $540.

What is the cheapest day to depart on your flight to Montego Bay?

What is the cheapest time of day to depart on your flight to Montego Bay?

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?

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 19% 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 September 2025, prices for Chicago to Montego Bay flights are approximately 20% more expensive when compared to flights at the same time last year.

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

Spirit Airlines, Frontier, and Southwest are the most popular carriers operating 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?

Fort Lauderdale (FLL) 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 Charlotte (CLT) offer the lowest average round-trip price of $384.

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

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 26m.

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

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 18m.

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

How far is Chicago to Montego Bay Sangster Intl by plane?

When did momondo last update prices for flights from Chicago to Montego Bay Sangster Intl Airport?

How many operators does momondo search for flights from Chicago to Montego Bay Sangster Intl Airport?

How old do you have to be to fly from Chicago to Montego Bay Sangster Intl Airport?

What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?

What is the most popular plane model from Chicago to Montego Bay?

What is the most popular airline 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?

Why should I use momondo to find a flight deal from Chicago to Montego Bay?

Can I find flights from Chicago to Montego Bay with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Montego Bay?

I’m not ready to book a flight from Chicago to Montego Bay right now. Can momondo alert me if prices change?

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