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Cheap flights from Chicago to Montego Bay from $115

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 1/6. 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.
Delta Logo
1:28 pm - 11:13 amMDW-MBJ
20h 45m2 stops
Delta Logo
4:45 pm - 8:52 amMBJ-MDW
17h 07m2 stops
$356Delta
Find Deal
Wed, Jan 7 - Wed, Jan 14
Delta Logo
5:59 pm - 12:32 pmORD-MBJ
17h 33m2 stops
Delta Logo
4:05 pm - 8:40 amMBJ-ORD
17h 35m1 stop
$356Delta
Find Deal
Wed, Jan 7 - Mon, Jan 12
Multiple Airlines Logo
8:27 pm - 12:02 pmORD-MBJ
14h 35m2 stops
Multiple Airlines Logo
12:57 pm - 11:22 amMBJ-ORD
23h 25m1 stop
$357Multiple Airlines
Find Deal
Sat, Jan 10 - Fri, Jan 16
Spirit Airlines Logo
5:15 am - 12:02 pmORD-MBJ
5h 47m1 stop
Spirit Airlines Logo
12:57 pm - 7:17 pmMBJ-ORD
7h 20m1 stop
$358Spirit Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
5:50 am - 3:31 pmORD-MBJ
8h 41m1 stop
Multiple Airlines Logo
12:57 pm - 11:22 amMBJ-ORD
23h 25m1 stop
$359Multiple Airlines
Find Deal
Sat, Jan 10 - Sun, Jan 11
Spirit Airlines Logo
5:15 am - 12:02 pmORD-MBJ
5h 47m1 stop
Spirit Airlines Logo
12:57 pm - 7:17 pmMBJ-ORD
7h 20m1 stop
$360Spirit Airlines
Find Deal
Fri, Jan 16 - Fri, Jan 23
Frontier Logo
6:33 pm - 8:59 amMDW-MBJ
13h 26m1 stop
Frontier Logo
3:47 pm - 10:12 pmMBJ-MDW
7h 25m1 stop
$361Frontier
Find Deal
Thu, Dec 18 - Mon, Dec 22
Multiple Airlines Logo
5:50 am - 3:31 pmORD-MBJ
8h 41m1 stop
Multiple Airlines Logo
12:57 pm - 11:22 amMBJ-ORD
23h 25m1 stop
$361Multiple Airlines
Find Deal
Sat, Jan 10 - Sun, Jan 11
Multiple Airlines Logo
8:27 pm - 12:02 pmORD-MBJ
14h 35m2 stops
Multiple Airlines Logo
12:57 pm - 8:57 pmMBJ-ORD
9h 00m1 stop
$362Multiple Airlines
Find Deal
Sat, Jan 10 - Thu, Jan 15
Frontier Logo
6:12 am - 2:29 pmMDW-MBJ
7h 17m1 stop
Frontier Logo
3:47 pm - 10:12 pmMBJ-MDW
7h 25m1 stop
$366Frontier
Find Deal
Thu, Dec 25 - Tue, Dec 30

Delta flights from Chicago to Montego Bay

Our best Delta deals on Chicago to Montego Bay flight tickets
Delta
Jan 7
ORD5:59 pmChicago O'Hare Intl
17h 33m
2 stops
MBJ12:32 pmMontego Bay Sangster Intl
Jan 16
MBJ12:38 pmMontego Bay Sangster Intl
12h 21m
1 stop
ORD11:59 pmChicago O'Hare Intl
$356
Find similar
Delta
Jan 4
ORD6:45 amChicago O'Hare Intl
6h 28m
1 stop
MBJ2:13 pmMontego Bay Sangster Intl
Jan 14
MBJ4:45 pmMontego Bay Sangster Intl
8h 14m
1 stop
ORD11:59 pmChicago O'Hare Intl
$398
Find similar
Delta
Jan 4
ORD5:30 amChicago O'Hare Intl
6h 28m
1 stop
MBJ12:58 pmMontego Bay Sangster Intl
Jan 14
MBJ4:45 pmMontego Bay Sangster Intl
17h 56m
2 stops
ORD9:41 amChicago O'Hare Intl
$399
Find similar

Air Canada flights from Chicago to Montego Bay

Our best Air Canada deals on Chicago to Montego Bay flight tickets
Air Canada
Dec 7
ORD8:15 pmChicago O'Hare Intl
16h 00m
1 stop
MBJ1:15 pmMontego Bay Sangster Intl
Dec 16
MBJ2:40 pmMontego Bay Sangster Intl
21h 38m
2 stops
ORD11:18 amChicago O'Hare Intl
$388
Find similar
Air Canada
Jan 7
ORD10:00 amChicago O'Hare Intl
25h 30m
1 stop
MBJ12:30 pmMontego Bay Sangster Intl
Jan 14
MBJ1:30 pmMontego Bay Sangster Intl
26h 40m
1 stop
ORD3:10 pmChicago O'Hare Intl
$389
Find similar
Air Canada
Dec 1
ORD8:15 pmChicago O'Hare Intl
15h 55m
1 stop
MBJ1:10 pmMontego Bay Sangster Intl
Dec 7
MBJ7:05 pmMontego Bay Sangster Intl
20h 50m
1 stop
ORD2:55 pmChicago O'Hare Intl
$391
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 26, 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

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 1/7

1:28 pm-11:13 am

2 stops20h 45m

Montego Bay Sangster Intl

Wed 1/14

4:45 pm-8:52 am

2 stops17h 07m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 1/7

5:59 pm-12:32 pm

2 stops17h 33m

Montego Bay Sangster Intl

Mon 1/12

4:05 pm-8:40 am

1 stop17h 35m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/10

8:27 pm-12:02 pm

2 stops14h 35m

Montego Bay Sangster Intl

Fri 1/16

12:57 pm-11:22 am

1 stop23h 25m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/9

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Mon 1/12

12:57 pm-7:17 pm

1 stop7h 20m

$358

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/10

5:50 am-3:31 pm

1 stop8h 41m

Montego Bay Sangster Intl

Sun 1/11

12:57 pm-11:22 am

1 stop23h 25m

$359

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/16

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Fri 1/23

12:57 pm-7:17 pm

1 stop7h 20m

$360

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 12/18

6:33 pm-8:59 am

1 stop13h 26m

Montego Bay Sangster Intl

Mon 12/22

3:47 pm-10:12 pm

1 stop7h 25m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/10

5:50 am-3:31 pm

1 stop8h 41m

Montego Bay Sangster Intl

Sun 1/11

12:57 pm-11:22 am

1 stop23h 25m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/10

8:27 pm-12:02 pm

2 stops14h 35m

Montego Bay Sangster Intl

Thu 1/15

12:57 pm-8:57 pm

1 stop9h 00m

$362

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 12/25

6:12 am-2:29 pm

1 stop7h 17m

Montego Bay Sangster Intl

Tue 12/30

3:47 pm-10:12 pm

1 stop7h 25m

$366

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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $556. 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 $688.

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 $611.

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 $590 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

$187

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 $187. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $473.
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
Spirit AirlinesPriceFrom $174Free CancellationRating
6.3
8,158 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
7,998 reviews
Search Delta flights
United AirlinesPriceFrom $358Free CancellationRating
7.4
9,046 reviews
Search United Airlines flights
FrontierPriceFrom $370Free CancellationRating
5.8
3,099 reviews
Search Frontier flights
American AirlinesPriceFrom $441Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,254 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 6 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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