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Cheap flights from Chicago Midway Airport to Montego Bay from $136

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 Midway Airport to Montego Bay departing on 1/10. 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 Midway Airport to Montego Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 3:20 pm
MDW
-
MBJ
8h 20m1 stop
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
$435Delta
Tue, Jan 27 - Sat, Jan 31
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
Delta Logo
4:44 pm - 12:46 pm
MBJ
-
MDW
21h 02m2 stops
$440Delta
Fri, Feb 27 - Thu, Mar 5
Frontier Logo
9:04 pm - 9:00 am
MDW
-
MBJ
10h 56m1 stop
Frontier Logo
10:40 am - 9:33 pm
MBJ
-
MDW
11h 53m1 stop
$443Frontier
Sun, Feb 15 - Sat, Feb 21
Multiple Airlines Logo
6:12 am - 8:59 am
MDW
-
MBJ
25h 47m1 stop
Multiple Airlines Logo
12:57 pm - 10:27 pm
MBJ
-
MDW
34h 30m2 stops
$456Multiple Airlines
Thu, Jan 1 - Fri, Jan 9
Delta Logo
6:25 am - 3:20 pm
MDW
-
MBJ
7h 55m1 stop
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
$461Delta
Sat, Jan 24 - Thu, Jan 29
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 9:00 pm
MBJ
-
MDW
8h 00m1 stop
$463Southwest
Wed, Feb 18 - Wed, Feb 25
Delta Logo
6:00 am - 3:29 pm
MDW
-
MBJ
9h 29m1 stop
Delta Logo
2:40 pm - 9:45 pm
MBJ
-
MDW
7h 05m1 stop
$466Delta
Wed, Apr 29 - Sat, May 2
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m2 stops
$468Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
9:40 pm - 11:35 am
MDW
-
MBJ
13h 55m2 stops
Southwest Logo
2:25 pm - 11:40 pm
MBJ
-
MDW
9h 15m1 stop
$471Southwest
Mon, Apr 6 - Fri, Apr 10
Southwest Logo
4:10 pm - 1:00 pm
MDW
-
MBJ
19h 50m2 stops
Southwest Logo
2:00 pm - 10:25 pm
MBJ
-
MDW
9h 25m1 stop
$478Southwest
Tue, Feb 3 - Fri, Feb 6

Delta flights from Chicago Midway Airport to Montego Bay

Our best Delta deals on Chicago Midway Airport to Montego Bay flight tickets
Delta
Feb 2
MDW6:00 amChicago Midway
5h 54m
1 stop
MBJ12:54 pmMontego Bay Sangster Intl
Feb 6
MBJ12:38 pmMontego Bay Sangster Intl
10h 44m
1 stop
MDW10:22 pmChicago Midway
$391
Find similar
Delta
Mar 10
MDW6:30 amChicago Midway
5h 43m
1 stop
MBJ12:13 pmMontego Bay Sangster Intl
Mar 17
MBJ4:55 pmMontego Bay Sangster Intl
15h 51m
2 stops
MDW8:46 amChicago Midway
$396
Find similar
Delta
Jan 22
MDW6:00 amChicago Midway
8h 20m
1 stop
MBJ3:20 pmMontego Bay Sangster Intl
Jan 29
MBJ4:45 pmMontego Bay Sangster Intl
6h 37m
1 stop
MDW10:22 pmChicago Midway
$413
Find similar

Frontier flights from Chicago Midway Airport to Montego Bay

Our best Frontier deals on Chicago Midway Airport to Montego Bay flight tickets
Frontier
Dec 25
MDW6:12 amChicago Midway
7h 17m
1 stop
MBJ2:29 pmMontego Bay Sangster Intl
Dec 30
MBJ3:47 pmMontego Bay Sangster Intl
7h 25m
1 stop
MDW10:12 pmChicago Midway
$392
Find similar
Frontier
Feb 15
MDW9:04 pmChicago Midway
10h 56m
1 stop
MBJ9:00 amMontego Bay Sangster Intl
Feb 21
MBJ10:40 amMontego Bay Sangster Intl
11h 53m
1 stop
MDW9:33 pmChicago Midway
$443
Find similar
Frontier
Dec 25
MDW6:12 amChicago Midway
25h 47m
1 stop
MBJ8:59 amMontego Bay Sangster Intl
Dec 31
MBJ10:24 amMontego Bay Sangster Intl
12h 48m
1 stop
MDW10:12 pmChicago Midway
$445
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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 December 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 1/27

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sat 1/31

4:45 pm-10:22 pm

1 stop6h 37m

$435

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 2/27

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Thu 3/5

4:44 pm-12:46 pm

2 stops21h 02m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/15

9:04 pm-9:00 am

1 stop10h 56m

Montego Bay Sangster Intl

Sat 2/21

10:40 am-9:33 pm

1 stop11h 53m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/1

6:12 am-8:59 am

1 stop25h 47m

Montego Bay Sangster Intl

Fri 1/9

12:57 pm-10:27 pm

2 stops34h 30m

$456

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/24

6:25 am-3:20 pm

1 stop7h 55m

Montego Bay Sangster Intl

Thu 1/29

4:45 pm-10:22 pm

1 stop6h 37m

$461

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/25

2:00 pm-9:00 pm

1 stop8h 00m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/29

6:00 am-3:29 pm

1 stop9h 29m

Montego Bay Sangster Intl

Sat 5/2

2:40 pm-9:45 pm

1 stop7h 05m

$466

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/25

2:00 pm-10:05 pm

2 stops9h 05m

$468

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 4/6

9:40 pm-11:35 am

2 stops13h 55m

Montego Bay Sangster Intl

Fri 4/10

2:25 pm-11:40 pm

1 stop9h 15m

$471

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/3

4:10 pm-1:00 pm

2 stops19h 50m

Montego Bay Sangster Intl

Fri 2/6

2:00 pm-10:25 pm

1 stop9h 25m

$478

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 Midway Airport 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 cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of October, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $622.

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 Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $552. 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 $691.

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 Midway Airport 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 $607.

What is the cheapest Chicago Midway to Montego Bay Sangster Intl flight route?

Fly from Chicago Midway to Montego Bay Sangster Intl for the best Chicago Midway - Montego Bay Sangster Intl flight prices

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

There is only 1 cabin class available to choose from on Chicago Midway 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 Midway Airport to Montego Bay flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago Midway Airport to Montego Bay flight.

When to book flights from Chicago Midway Airport to Montego Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Montego Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Montego Bay (MDW to MBJ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Montego Bay

Best Price Found

$459

Fastest flight time

3h 50m

Direct flights

Mon, Wed and Sun

Airports in Montego Bay

1 airport
The best flight deal from Chicago Midway Airport to Montego Bay found on momondo in the last 72 hours is $459
The fastest flight from Chicago Midway Airport to Montego Bay takes 3h 50m
Direct flights go from Chicago Midway Airport to Montego Bay on Monday, Wednesday and Sunday. There are no airlines offering direct flights.
There is 1 airport in Montego Bay. From Chicago Midway Airport there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

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

    Chicago Midway and Montego Bay Sangster Intl are 1710.6 mi apart from one another. A reasonable flight in good conditions will take 3h 50m.

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

    Prices for flights from Chicago Midway Airport to Montego Bay Sangster Intl Airport are updated daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport 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 Midway Airport to Montego Bay?

  • What is the most popular airline from Chicago Midway Airport to Montego Bay?

Best airlines flying from Chicago Midway Airport to Montego Bay

Compare and see reviews for airlines that fly from Chicago Midway Airport to Montego Bay with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $341Free CancellationRating
5.8
3,077 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
8,014 reviews
Search Delta flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,253 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Montego Bay

    Across 1 Southwest flight from Chicago Midway Airport to Montego Bay this week, the average price was $727, with the best Southwest deals starting from $549 round-trip. 4,253 users have rated Southwest on momondo, with an average score of 8.0/10.

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?

It is quick and easy to find Chicago to Montego Bay flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Montego Bay that suits you.

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

Yes. momondo enables you to select and highlight flights to Montego Bay from Chicago with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight 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?

Yes. momondo can track prices for Chicago to Montego Bay flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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