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Cheap flights from Montego Bay to Chicago from $177

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montego Bay to Chicago departing on 2/12. 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 Montego Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
Delta Logo
6:00 am - 12:53 pm
MDW
-
MBJ
5h 53m1 stop
$443Delta
Tue, Feb 10 - Sun, Feb 22
Delta Logo
2:19 pm - 10:22 pm
MBJ
-
MDW
9h 03m1 stop
Delta Logo
6:00 am - 3:20 pm
MDW
-
MBJ
8h 20m1 stop
$486Delta
Mon, Feb 2 - Mon, Feb 9
WestJet Logo
7:25 pm - 12:46 pm
MBJ
-
MDW
18h 21m2 stops
WestJet Logo
10:46 am - 7:17 pm
MDW
-
MBJ
31h 31m2 stops
$1,139WestJet
Mon, Feb 2 - Mon, Feb 9
WestJet Logo
8:25 pm - 1:06 pm
MBJ
-
MDW
17h 41m2 stops
WestJet Logo
6:17 pm - 7:17 pm
MDW
-
MBJ
48h 00m2 stops
$1,179WestJet
Tue, Feb 10 - Sun, Feb 22

Delta flights from Montego Bay to Chicago Midway Airport

Our best Delta deals on Montego Bay to Chicago Midway Airport flight tickets
Delta
Feb 10
MBJ4:45 pmMontego Bay Sangster Intl
6h 37m
1 stop
MDW10:22 pmChicago Midway
Feb 22
MDW6:00 amChicago Midway
5h 53m
1 stop
MBJ12:53 pmMontego Bay Sangster Intl
$443
Find similar
Delta
Feb 2
MBJ2:19 pmMontego Bay Sangster Intl
9h 03m
1 stop
MDW10:22 pmChicago Midway
Feb 9
MDW6:00 amChicago Midway
8h 20m
1 stop
MBJ3:20 pmMontego Bay Sangster Intl
$486
Find similar

WestJet flights from Montego Bay to Chicago Midway Airport

Our best WestJet deals on Montego Bay to Chicago Midway Airport flight tickets
WestJet
Feb 2
MBJ7:25 pmMontego Bay Sangster Intl
18h 21m
2 stops
MDW12:46 pmChicago Midway
Feb 9
MDW10:46 amChicago Midway
31h 31m
2 stops
MBJ7:17 pmMontego Bay Sangster Intl
$1,139
Find similar
WestJet
Feb 10
MBJ8:25 pmMontego Bay Sangster Intl
17h 41m
2 stops
MDW1:06 pmChicago Midway
Feb 22
MDW6:17 pmChicago Midway
48h 00m
2 stops
MBJ7:17 pmMontego Bay Sangster Intl
$1,179
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montego Bay to Chicago Midway Airport 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 21, 2025.
Use the filters below to find and compare flights from Montego Bay to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 2/10

4:45 pm-10:22 pm

1 stop6h 37m

Chicago Midway

Sun 2/22

6:00 am-12:53 pm

1 stop5h 53m

$443

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 2/2

2:19 pm-10:22 pm

1 stop9h 03m

Chicago Midway

Mon 2/9

6:00 am-3:20 pm

1 stop8h 20m

$486

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 2/2

7:25 pm-12:46 pm

2 stops18h 21m

Chicago Midway

Mon 2/9

10:46 am-7:17 pm

2 stops31h 31m

$1,139

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 2/10

8:25 pm-1:06 pm

2 stops17h 41m

Chicago Midway

Sun 2/22

6:17 pm-7:17 pm

2 stops48h 00m

$1,179

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 2/12

3:08 pm-10:34 pm

1 stop8h 26m

$177

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 2/21

10:40 am-9:33 pm

1 stop11h 53m

$180

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 1/24

2:35 pm-11:45 am

1 stop22h 10m

$192

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 1/17

5:03 pm-8:03 am

1 stop16h 00m

$195

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/31

10:24 am-10:12 pm

1 stop12h 48m

$196

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 2/14

11:44 am-9:08 pm

1 stop10h 24m

$197

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Montego Bay to Chicago Midway Airport

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Montego Bay. The lowest ticket price found for a Saturday departure recently was $532. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Montego Bay because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $689.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Montego Bay at noon is the least expensive time of day to depart. momondo users have found prices as low as $549 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $763. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

You could potentially save up to 24% on your flight if you consider stops on a Montego Bay to Chicago Midway Airport flight.

When to book flights from Montego Bay to Chicago Midway Airport

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

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

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

Fastest flight time

6h 37m

Direct flights

Mon and Sun
The fastest flight from Montego Bay to Chicago Midway Airport takes 6h 37m
Direct flights go from Montego Bay to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

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

    The straight-line distance from Montego Bay Sangster Intl to Chicago Midway is 1710.6 mi. A reasonable flight in good conditions will take 6h 37m.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Montego Bay Sangster Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Montego Bay to Chicago Midway Airport

Compare and see reviews for airlines that fly from Montego Bay to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $392Free CancellationRating
8.0
4,257 reviews
Search Southwest flights

  • Southwest Flights From Montego Bay to Chicago Midway Airport

    Southwest operates around 1 flight from Montego Bay to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $536, but momondo users have found Southwest deals from Montego Bay to Chicago Midway Airport from as low as $392 round-trip. Southwest has been scored 8.0/10 in 4,257 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Montego Bay to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Montego Bay to Chicago for you.

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

momondo does allow users to show only those flights to Chicago from Montego Bay which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Montego Bay to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Montego Bay to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Montego Bay to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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