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Cheap flights from Chicago Midway Airport to Montego Bay from $154

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 11/8. 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

Frontier Logo
6:20 am - 3:15 pmMDW-MBJ
7h 55m1 stop
Frontier Logo
4:53 pm - 11:06 pmMBJ-MDW
7h 13m1 stop
$398Frontier
Find Deal
vie., nov. 14 - jue., nov. 20
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
Frontier Logo
3:51 pm - 11:25 pmMBJ-MDW
7h 34m1 stop
$399Frontier
Find Deal
vie., oct. 3 - vie., oct. 10
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
Frontier Logo
2:05 pm - 11:17 pmMBJ-MDW
9h 12m1 stop
$402Frontier
Find Deal
lun., sep. 29 - sáb., oct. 4
Frontier Logo
9:26 pm - 2:36 pmMDW-MBJ
17h 10m1 stop
Frontier Logo
3:51 pm - 1:38 pmMBJ-MDW
21h 47m1 stop
$403Frontier
Find Deal
jue., oct. 16 - lun., oct. 20
Logo
8:15 am - 11:05 amMDW-MBJ
26h 50m2 stops
Logo
2:05 pm - 11:41 pmMBJ-MDW
9h 36m1 stop
$404
Find Deal
lun., sep. 29 - sáb., oct. 4
Southwest Logo
7:05 am - 1:55 pmMDW-MBJ
6h 50m1 stop
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
$420Southwest
Find Deal
lun., oct. 20 - vie., oct. 24
Southwest Logo
8:45 pm - 2:00 pmMDW-MBJ
17h 15m2 stops
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
$424Southwest
Find Deal
lun., oct. 20 - vie., oct. 24
Delta Logo
6:00 am - 4:33 pmMDW-MBJ
9h 33m1 stop
Delta Logo
5:58 pm - 9:51 amMBJ-MDW
16h 53m1 stop
$425Delta
Find Deal
dom., nov. 16 - mié., nov. 26
Delta Logo
1:00 pm - 12:41 pmMDW-MBJ
22h 41m2 stops
Delta Logo
5:58 pm - 12:32 pmMBJ-MDW
19h 34m2 stops
$429Delta
Find Deal
dom., nov. 16 - mar., nov. 25
Logo
1:49 pm - 9:47 amMDW-MBJ
19h 58m1 stop
Logo
12:10 pm - 7:23 amMBJ-MDW
19h 13m2 stops
$473
Find Deal
jue., sep. 25 - dom., sep. 28

Frontier flights from Chicago Midway Airport to Montego Bay

Our best Frontier deals on Chicago Midway Airport to Montego Bay flight tickets
Frontier
Nov 14
MDW6:20 amChicago Midway
7h 55m
1 stop
MBJ3:15 pmMontego Bay Sangster Intl
Nov 20
MBJ4:53 pmMontego Bay Sangster Intl
7h 13m
1 stop
MDW11:06 pmChicago Midway
$398
Find similar
Frontier
Oct 3
MDW6:20 amChicago Midway
6h 25m
1 stop
MBJ12:45 pmMontego Bay Sangster Intl
Oct 10
MBJ3:51 pmMontego Bay Sangster Intl
7h 34m
1 stop
MDW11:25 pmChicago Midway
$399
Find similar
Frontier
Sep 29
MDW6:20 amChicago Midway
6h 25m
1 stop
MBJ12:45 pmMontego Bay Sangster Intl
Oct 4
MBJ2:05 pmMontego Bay Sangster Intl
9h 12m
1 stop
MDW11:17 pmChicago Midway
$402
Find similar

Delta flights from Chicago Midway Airport to Montego Bay

Our best Delta deals on Chicago Midway Airport to Montego Bay flight tickets
Delta
Nov 16
MDW6:00 amChicago Midway
9h 33m
1 stop
MBJ4:33 pmMontego Bay Sangster Intl
Nov 26
MBJ5:58 pmMontego Bay Sangster Intl
16h 53m
1 stop
MDW9:51 amChicago Midway
$425
Find similar
Delta
Nov 16
MDW1:00 pmChicago Midway
22h 41m
2 stops
MBJ12:41 pmMontego Bay Sangster Intl
Nov 25
MBJ5:58 pmMontego Bay Sangster Intl
19h 34m
2 stops
MDW12:32 pmChicago Midway
$429
Find similar
Delta
Nov 16
MDW5:59 pmChicago Midway
17h 42m
2 stops
MBJ12:41 pmMontego Bay Sangster Intl
Nov 20
MBJ3:32 pmMontego Bay Sangster Intl
28h 04m
2 stops
MDW6:36 pmChicago Midway
$462
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 agosto 21, 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

vie. 11/14

6:20 am-3:15 pm

1 stop7h 55m

Montego Bay Sangster Intl

jue. 11/20

4:53 pm-11:06 pm

1 stop7h 13m

$398

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 10/3

6:20 am-12:45 pm

1 stop6h 25m

Montego Bay Sangster Intl

vie. 10/10

3:51 pm-11:25 pm

1 stop7h 34m

$399

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 9/29

6:20 am-12:45 pm

1 stop6h 25m

Montego Bay Sangster Intl

sáb. 10/4

2:05 pm-11:17 pm

1 stop9h 12m

$402

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jue. 10/16

9:26 pm-2:36 pm

1 stop17h 10m

Montego Bay Sangster Intl

lun. 10/20

3:51 pm-1:38 pm

1 stop21h 47m

$403

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 9/29

8:15 am-11:05 am

2 stops26h 50m

Montego Bay Sangster Intl

sáb. 10/4

2:05 pm-11:41 pm

1 stop9h 36m

$404

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 10/20

7:05 am-1:55 pm

1 stop6h 50m

Montego Bay Sangster Intl

vie. 10/24

12:50 pm-8:40 pm

2 stops7h 50m

$420

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 10/20

8:45 pm-2:00 pm

2 stops17h 15m

Montego Bay Sangster Intl

vie. 10/24

12:50 pm-8:40 pm

2 stops7h 50m

$424

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 11/16

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

mié. 11/26

5:58 pm-9:51 am

1 stop16h 53m

$425

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 11/16

1:00 pm-12:41 pm

2 stops22h 41m

Montego Bay Sangster Intl

mar. 11/25

5:58 pm-12:32 pm

2 stops19h 34m

$429

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

jue. 9/25

1:49 pm-9:47 am

1 stop19h 58m

Montego Bay Sangster Intl

dom. 9/28

12:10 pm-7:23 am

2 stops19h 13m

$473

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 July, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $625.

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 Sunday. momondo users have found tickets for Sunday departures for as low as $537. 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 $680.

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

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 Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Montego Bay for around $725 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 Midway Airport for as low as $507 on momondo.

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

There are 1 cabin classes 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 13% 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

Fastest flight time

3h 55m

Direct flights

Sun

Airports in Montego Bay

1 airport
The fastest flight from Chicago Midway Airport to Montego Bay takes 3h 55m
Direct flights go from Chicago Midway Airport to Montego Bay on Sunday. There are no airlines offering direct flights.
There is 1 airport near Montego Bay: 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 6h 21m.

  • 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
DeltaPriceFrom $448Free CancellationRating
7.9
7,981 reviews
Search Delta flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,245 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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