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Cheap flights from Chicago to Montego Bay from $113

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 12/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Montego Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:05 am - 2:29 pmORD-MBJ
7h 24m1 stop
Frontier Logo
3:47 pm - 10:24 pmMBJ-ORD
7h 37m1 stop
$356Frontier
Find Deal
Wed, Dec 24 - Thu, Jan 1
Multiple Airlines Logo
2:49 pm - 12:10 pmMDW-MBJ
20h 21m2 stops
Multiple Airlines Logo
3:31 pm - 8:46 amMBJ-MDW
18h 15m1 stop
$356Multiple Airlines
Find Deal
Wed, Dec 10 - Mon, Dec 15
Spirit Airlines Logo
3:26 pm - 12:10 pmORD-MBJ
19h 44m1 stop
Spirit Airlines Logo
1:05 pm - 6:39 pmMBJ-ORD
6h 34m1 stop
$358Spirit Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 18
Multiple Airlines Logo
4:01 pm - 12:05 pmORD-MBJ
19h 04m2 stops
Multiple Airlines Logo
1:05 pm - 3:02 pmMBJ-ORD
26h 57m1 stop
$360Multiple Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 24
Multiple Airlines Logo
8:42 pm - 3:51 pmMDW-MBJ
18h 09m1 stop
Multiple Airlines Logo
1:05 pm - 8:46 amMBJ-MDW
20h 41m2 stops
$360Multiple Airlines
Find Deal
Fri, Dec 12 - Tue, Dec 16
Spirit Airlines Logo
4:38 pm - 12:10 pmORD-MBJ
18h 32m2 stops
Spirit Airlines Logo
1:05 pm - 6:39 pmMBJ-ORD
6h 34m1 stop
$363Spirit Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 18
American Airlines Logo
10:15 am - 3:22 pmORD-MBJ
4h 07mnonstop
American Airlines Logo
3:12 pm - 6:59 pmMBJ-ORD
4h 47mnonstop
$364American Airlines
Find Deal
Mon, Dec 8 - Sat, Dec 13
American Airlines Logo
10:22 am - 3:29 pmORD-MBJ
4h 07mnonstop
American Airlines Logo
2:14 pm - 6:00 pmMBJ-ORD
4h 46mnonstop
$365American Airlines
Find Deal
Tue, Feb 17 - Wed, Feb 25
Delta Logo
6:00 am - 8:41 pmMDW-MBJ
13h 41m1 stop
Delta Logo
8:00 am - 2:44 pmMBJ-MDW
7h 44m1 stop
$379Delta
Find Deal
Thu, Dec 25 - Wed, Dec 31
Delta Logo
9:34 am - 1:04 pmMDW-MBJ
26h 30m2 stops
Delta Logo
8:00 am - 2:44 pmMBJ-MDW
7h 44m1 stop
$384Delta
Find Deal
Wed, Dec 17 - Wed, Dec 24

Frontier flights from Chicago to Montego Bay

Our best Frontier deals on Chicago to Montego Bay flight tickets
Frontier
Dec 24
ORD6:05 amChicago O'Hare Intl
7h 24m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
Jan 1
MBJ3:47 pmMontego Bay Sangster Intl
7h 37m
1 stop
ORD10:24 pmChicago O'Hare Intl
$356
Find similar
Frontier
Dec 24
MDW6:12 amChicago Midway
7h 17m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
Dec 31
MBJ3:49 pmMontego Bay Sangster Intl
7h 23m
1 stop
MDW10:12 pmChicago Midway
$362
Find similar
Frontier
Dec 18
ORD6:00 amChicago O'Hare Intl
7h 29m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
Jan 1
MBJ3:47 pmMontego Bay Sangster Intl
7h 37m
1 stop
ORD10:24 pmChicago O'Hare Intl
$370
Find similar

American Airlines flights from Chicago to Montego Bay

Our best American Airlines deals on Chicago to Montego Bay flight tickets
American Airlines
Dec 8
ORD10:15 amChicago O'Hare Intl
4h 07m
MBJ3:22 pmMontego Bay Sangster Intl
Dec 13
MBJ3:12 pmMontego Bay Sangster Intl
4h 47m
ORD6:59 pmChicago O'Hare Intl
$364
Find similar
American Airlines
Feb 17
ORD10:22 amChicago O'Hare Intl
4h 07m
MBJ3:29 pmMontego Bay Sangster Intl
Feb 25
MBJ2:14 pmMontego Bay Sangster Intl
4h 46m
ORD6:00 pmChicago O'Hare Intl
$365
Find similar
American Airlines
Feb 17
ORD5:00 amChicago O'Hare Intl
7h 39m
1 stop
MBJ1:39 pmMontego Bay Sangster Intl
Feb 24
MBJ4:35 pmMontego Bay Sangster Intl
4h 39m
ORD8:14 pmChicago O'Hare Intl
$369
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Montego Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 18, 2025.
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 12/24

6:05 am-2:29 pm

1 stop7h 24m

Montego Bay Sangster Intl

Thu 1/1

3:47 pm-10:24 pm

1 stop7h 37m

$356

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 12/10

2:49 pm-12:10 pm

2 stops20h 21m

Montego Bay Sangster Intl

Mon 12/15

3:31 pm-8:46 am

1 stop18h 15m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

3:26 pm-12:10 pm

1 stop19h 44m

Montego Bay Sangster Intl

Thu 12/18

1:05 pm-6:39 pm

1 stop6h 34m

$358

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 12/17

4:01 pm-12:05 pm

2 stops19h 04m

Montego Bay Sangster Intl

Wed 12/24

1:05 pm-3:02 pm

1 stop26h 57m

$360

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 12/12

8:42 pm-3:51 pm

1 stop18h 09m

Montego Bay Sangster Intl

Tue 12/16

1:05 pm-8:46 am

2 stops20h 41m

$360

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

4:38 pm-12:10 pm

2 stops18h 32m

Montego Bay Sangster Intl

Thu 12/18

1:05 pm-6:39 pm

1 stop6h 34m

$363

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

10:15 am-3:22 pm

Nonstop4h 07m

Montego Bay Sangster Intl

Sat 12/13

3:12 pm-6:59 pm

Nonstop4h 47m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/17

10:22 am-3:29 pm

Nonstop4h 07m

Montego Bay Sangster Intl

Wed 2/25

2:14 pm-6:00 pm

Nonstop4h 46m

$365

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 12/25

6:00 am-8:41 pm

1 stop13h 41m

Montego Bay Sangster Intl

Wed 12/31

8:00 am-2:44 pm

1 stop7h 44m

$379

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 12/17

9:34 am-1:04 pm

2 stops26h 30m

Montego Bay Sangster Intl

Wed 12/24

8:00 am-2:44 pm

1 stop7h 44m

$384

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Montego Bay from

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 September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $546.

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 $557. 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 $690.

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 $613.

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 $592 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 $536 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 5% 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 November 2025, prices for Chicago to Montego Bay flights are approximately 9% 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

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

$195

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 $195. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $421.
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 55m.

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $186Free CancellationRating
7.9
8,008 reviews
Search Delta flights
Spirit AirlinesPriceFrom $194Free CancellationRating
6.3
8,146 reviews
Search Spirit Airlines flights
FrontierPriceFrom $333Free CancellationRating
5.8
3,103 reviews
Search Frontier flights
United AirlinesPriceFrom $373Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights
American AirlinesPriceFrom $441Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,245 reviews
Search Southwest flights

  • American Airlines Flights From Chicago to Montego Bay

    American Airlines flight deals from Chicago to Montego Bay start from $441 round-trip. Over the 3 American Airlines flights for this route in a normal week, average airfare is usually $597 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
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.

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