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Cheap flights from Chicago Midway Airport to Montego Bay from $137

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 7/18. 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
6:05 am - 1:01 pm
MDW
-
MBJ
6h 56m
1 stop
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
$352Delta
Sat, Aug 15 - Fri, Aug 21
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
2:26 pm - 9:17 am
MBJ
-
MDW
18h 51m
2 stops
$357Delta
Sat, Aug 15 - Thu, Aug 27
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
$399Delta
Fri, Aug 14 - Wed, Aug 26
Delta Logo
6:05 am - 11:44 am
MDW
-
MBJ
5h 39m
1 stop
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
$425Delta
Sun, Aug 16 - Thu, Aug 20
Delta Logo
6:05 am - 11:44 am
MDW
-
MBJ
5h 39m
1 stop
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
$440Delta
Sun, Aug 16 - Tue, Aug 25
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
$443Delta
Sun, Aug 9 - Sat, Aug 15
Southwest Logo
7:15 am - 1:15 pm
MDW
-
MBJ
6h 00m
1 stop
Southwest Logo
12:55 pm - 11:10 pm
MBJ
-
MDW
10h 15m
2 stops
$445Southwest
Fri, Aug 14 - Tue, Aug 18
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
$446Delta
Mon, Aug 3 - Fri, Aug 7
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
$452Frontier
Tue, Jul 7 - Tue, Jul 14
Southwest Logo
10:10 am - 2:00 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
2:30 pm - 11:15 pm
MBJ
-
MDW
8h 45m
1 stop
$456Southwest
Sat, Jul 4 - Sat, Jul 11

Frontier flights from Chicago Midway Airport to Montego Bay

Our best Frontier deals on Chicago Midway Airport to Montego Bay flight tickets
Frontier
Jul 7
MDW6:05 amChicago Midway
6h 22m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Jul 14
MBJ1:32 pmMontego Bay Sangster Intl
8h 31m
1 stop
MDW10:03 pmChicago Midway
$452
Frontier
Jul 15
MDW6:05 amChicago Midway
6h 22m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Jul 19
MBJ1:39 pmMontego Bay Sangster Intl
8h 24m
1 stop
MDW10:03 pmChicago Midway
$472
Frontier
Jul 13
MDW6:05 amChicago Midway
6h 22m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Jul 17
MBJ1:32 pmMontego Bay Sangster Intl
8h 31m
1 stop
MDW10:03 pmChicago Midway
$492

Southwest flights from Chicago Midway Airport to Montego Bay

Our best Southwest deals on Chicago Midway Airport to Montego Bay flight tickets
Southwest
Aug 14
MDW7:15 amChicago Midway
6h 00m
1 stop
MBJ1:15 pmMontego Bay Sangster Intl
Aug 18
MBJ12:55 pmMontego Bay Sangster Intl
10h 15m
2 stops
MDW11:10 pmChicago Midway
$445
Southwest
Jul 4
MDW10:10 amChicago Midway
3h 50m
MBJ2:00 pmMontego Bay Sangster Intl
Jul 11
MBJ2:30 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW11:15 pmChicago Midway
$456
Southwest
Jul 25
MDW5:05 amChicago Midway
8h 25m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
Jul 29
MBJ2:20 pmMontego Bay Sangster Intl
7h 45m
1 stop
MDW10:05 pmChicago Midway
$457

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 May 29, 2026.
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

Cheapest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/15

6:05 am-1:01 pm

1 stop6h 56m

Montego Bay Sangster Intl

Fri 8/21

2:26 pm-10:36 pm

1 stop8h 10m

$352

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/15

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Thu 8/27

2:26 pm-9:17 am

2 stops18h 51m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 8/14

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Wed 8/26

1:09 pm-10:36 pm

1 stop9h 27m

$399

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

6:05 am-11:44 am

1 stop5h 39m

Montego Bay Sangster Intl

Thu 8/20

2:26 pm-10:36 pm

1 stop8h 10m

$425

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

6:05 am-11:44 am

1 stop5h 39m

Montego Bay Sangster Intl

Tue 8/25

2:26 pm-10:36 pm

1 stop8h 10m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/9

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Sat 8/15

2:26 pm-10:36 pm

1 stop8h 10m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 8/14

7:15 am-1:15 pm

1 stop6h 00m

Montego Bay Sangster Intl

Tue 8/18

12:55 pm-11:10 pm

2 stops10h 15m

$445

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 8/3

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Fri 8/7

1:09 pm-10:36 pm

1 stop9h 27m

$446

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/7

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Tue 7/14

1:32 pm-10:03 pm

1 stop8h 31m

$452
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/4

10:10 am-2:00 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 7/11

2:30 pm-11:15 pm

1 stop8h 45m

$456

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 typical price of a round-trip flight between Chicago Midway Airport 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 April is also cheap. Prices for this month can be found on momondo for an average of $522.

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 $494. 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 $640.

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 Airport to Montego Bay flights?

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

You could potentially save up to 21% 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

$497

Fastest flight time

3h 55m

Direct flights

Mon 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 $497
The fastest flight from Chicago Midway Airport to Montego Bay takes 3h 55m
Direct flights go from Chicago Midway Airport to Montego Bay on Monday 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

Frequently asked questions about flying from Chicago Midway Airport to Montego Bay

  • 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 55m.

  • 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 $172Free CancellationRating
5.6
2,929 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
8,419 reviews
Search Delta flights
SouthwestPriceFrom $468Free CancellationRating
8.0
4,264 reviews
Search Southwest flights

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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