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 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.

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?

American Airlines, Delta, and JetBlue 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 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.

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.

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.

$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 $385.

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.

9:05 pm - 4:08 pm

ORD

MBJ

19h 03m

1 stop

2:12 pm - 6:55 pm

MBJ

ORD

4h 43mnonstop

$385American Airlines

Fri, Sep 4 - Tue, Sep 8

9:00 am - 1:12 pm

ORD

MBJ

4h 12mnonstop

2:12 pm - 6:55 pm

MBJ

ORD

4h 43mnonstop

$387American Airlines

Mon, Aug 24 - Thu, Aug 27

9:00 am - 1:12 pm

ORD

MBJ

4h 12mnonstop

2:12 pm - 6:55 pm

MBJ

ORD

4h 43mnonstop

$388American Airlines

Sun, Aug 16 - Thu, Aug 20

5:59 pm - 4:12 pm

ORD

MBJ

22h 13m

1 stop

5:13 pm - 7:42 am

MBJ

ORD

14h 29m

1 stop

$390American Airlines

Sat, Oct 10 - Thu, Oct 15

7:52 pm - 11:43 am

ORD

MBJ

15h 51m

1 stop

2:01 pm - 6:27 pm

MBJ

ORD

4h 26mnonstop

$392United Airlines

Fri, Oct 23 - Fri, Oct 30

7:00 am - 1:48 pm

ORD

MBJ

6h 48m

1 stop

2:00 pm - 11:44 pm

MBJ

ORD

10h 44m

1 stop

$394JetBlue

Fri, Oct 30 - Fri, Nov 13

6:00 am - 12:55 pm

MDW

MBJ

5h 55m

1 stop

4:00 pm - 8:49 am

MBJ

MDW

17h 49m

1 stop

$402Delta

Mon, Nov 9 - Sat, Nov 14

5:30 am - 4:34 pm

ORD

MBJ

10h 04m

1 stop

6:00 pm - 11:50 pm

MBJ

ORD

6h 50m

1 stop

$402Delta

Sun, Nov 8 - Fri, Nov 13

5:00 am - 1:30 pm

MDW

MBJ

8h 30m

2 stops

12:20 pm - 8:55 pm

MBJ

MDW

8h 35m

1 stop

$440Southwest

Sun, Aug 23 - Sat, Aug 29

5:05 am - 2:25 pm

MDW

MBJ

8h 20m

1 stop

3:45 pm - 9:10 pm

MBJ

MDW

6h 25m

1 stop

$448Southwest

Mon, Nov 9 - Wed, Nov 18

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United Airlines flights from Chicago to Montego Bay

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

United Airlines

Oct 23

ORD9:38 pmChicago O'Hare Intl

15h 52m

1 stop

MBJ1:30 pmMontego Bay Sangster Intl

Oct 30

MBJ2:20 pmMontego Bay Sangster Intl

9h 22m

1 stop

ORD11:42 pmChicago O'Hare Intl

$392

United Airlines

Sep 11

ORD9:35 pmChicago O'Hare Intl

15h 55m

1 stop

MBJ1:30 pmMontego Bay Sangster Intl

Sep 15

MBJ12:52 pmMontego Bay Sangster Intl

9h 23m

1 stop

ORD10:15 pmChicago O'Hare Intl

$422

United Airlines

Oct 16

ORD9:38 pmChicago O'Hare Intl

15h 52m

1 stop

MBJ1:30 pmMontego Bay Sangster Intl

Oct 19

MBJ12:52 pmMontego Bay Sangster Intl

9h 36m

1 stop

ORD10:28 pmChicago O'Hare Intl

$431

Frontier flights from Chicago to Montego Bay

Our best Frontier deals on Chicago to Montego Bay flight tickets

Frontier

Aug 12

MDW6:05 amChicago Midway

6h 22m

1 stop

MBJ12:27 pmMontego Bay Sangster Intl

Aug 16

MBJ1:39 pmMontego Bay Sangster Intl

8h 24m

1 stop

MDW10:03 pmChicago Midway

$487

Frontier

Sep 30

MDW12:03 pmChicago Midway

25h 28m

1 stop

MBJ1:31 pmMontego Bay Sangster Intl

Oct 5

MBJ2:49 pmMontego Bay Sangster Intl

7h 09m

1 stop

MDW9:58 pmChicago Midway

$491

Frontier

Aug 8

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

$492

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 9/4

9:05 pm-4:08 pm

1 stop19h 03m

Montego Bay Sangster Intl

Tue 9/8

2:12 pm-6:55 pm

Nonstop4h 43m

$385

Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 8/24

9:00 am-1:12 pm

Nonstop4h 12m

Montego Bay Sangster Intl

Thu 8/27

2:12 pm-6:55 pm

Nonstop4h 43m

$387

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

9:00 am-1:12 pm

Nonstop4h 12m

Montego Bay Sangster Intl

Thu 8/20

2:12 pm-6:55 pm

Nonstop4h 43m

$388

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 10/10

5:59 pm-4:12 pm

1 stop22h 13m

Montego Bay Sangster Intl

Thu 10/15

5:13 pm-7:42 am

1 stop14h 29m

$390

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/23

7:52 pm-11:43 am

1 stop15h 51m

Montego Bay Sangster Intl

Fri 10/30

2:01 pm-6:27 pm

Nonstop4h 26m

$392

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

Fri 11/13

2:00 pm-11:44 pm

1 stop10h 44m

$394

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 11/9

6:00 am-12:55 pm

1 stop5h 55m

Montego Bay Sangster Intl

Sat 11/14

4:00 pm-8:49 am

1 stop17h 49m

$402

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 11/8

5:30 am-4:34 pm

1 stop10h 04m

Montego Bay Sangster Intl

Fri 11/13

6:00 pm-11:50 pm

1 stop6h 50m

$402

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/23

5:00 am-1:30 pm

2 stops8h 30m

Montego Bay Sangster Intl

Sat 8/29

12:20 pm-8:55 pm

1 stop8h 35m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 11/9

5:05 am-2:25 pm

1 stop8h 20m

Montego Bay Sangster Intl

Wed 11/18

3:45 pm-9:10 pm

1 stop6h 25m

$448

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 $487. 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 $617.

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	$268
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 $268. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $603.

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 2,794 reviews	Search Frontier flights
Delta	PriceFrom $162	Free Cancellation	Rating 7.8 8,476 reviews	Search Delta flights
JetBlue	PriceFrom $297	Free Cancellation	Rating 7.1 3,012 reviews	Search JetBlue flights
United Airlines	PriceFrom $297	Free Cancellation	Rating 7.4 10,006 reviews	Search United Airlines flights
American Airlines	PriceFrom $318	Free Cancellation	Rating 7.1 11,825 reviews	Search American Airlines flights
Southwest	PriceFrom $467	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights

American Airlines Flights From Chicago to Montego Bay
American Airlines flight deals from Chicago to Montego Bay start from $318 round-trip. Over the 7 American Airlines flights for this route in a normal week, average airfare is usually $541 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 $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 8/25. 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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United Airlines flights from Chicago to Montego Bay

Our best United Airlines 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

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

Airports servicing 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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