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Cheap flights from Montego Bay to Chicago from $245

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 10/28. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Montego Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:14 pm - 10:45 pm
MBJ
-
MDW
9h 31m
1 stop
Delta Logo
6:05 am - 11:48 am
MDW
-
MBJ
5h 43m
1 stop
$397Delta
Thu, Sep 17 - Tue, Sep 22
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
Delta Logo
9:59 am - 11:33 am
MDW
-
MBJ
25h 34m
2 stops
$403Delta
Wed, Sep 2 - Mon, Sep 14
Delta Logo
4:59 pm - 9:17 am
MBJ
-
MDW
16h 18m
2 stops
Delta Logo
6:40 pm - 11:48 am
MDW
-
MBJ
17h 08m
2 stops
$403Delta
Sat, Sep 5 - Sat, Sep 19
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
Delta Logo
6:40 pm - 3:35 pm
MDW
-
MBJ
20h 55m
2 stops
$403Delta
Wed, Sep 2 - Sat, Sep 19
Delta Logo
1:09 pm - 9:07 am
MBJ
-
MDW
19h 58m
2 stops
Delta Logo
7:01 pm - 11:33 am
MDW
-
MBJ
16h 32m
2 stops
$403Delta
Mon, Sep 7 - Mon, Sep 14
Delta Logo
2:26 pm - 9:17 am
MBJ
-
MDW
18h 51m
2 stops
Delta Logo
7:01 pm - 11:33 am
MDW
-
MBJ
16h 32m
2 stops
$403Delta
Fri, Sep 4 - Fri, Sep 18
Delta Logo
4:59 pm - 9:17 am
MBJ
-
MDW
16h 18m
2 stops
Delta Logo
7:01 pm - 11:48 am
MDW
-
MBJ
16h 47m
2 stops
$403Delta
Sat, Sep 5 - Sun, Sep 20
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
Delta Logo
7:01 pm - 11:48 am
MDW
-
MBJ
16h 47m
2 stops
$403Delta
Wed, Sep 2 - Sun, Sep 20
Delta Logo
4:59 pm - 9:17 am
MBJ
-
MDW
16h 18m
2 stops
Delta Logo
7:01 pm - 11:33 am
MDW
-
MBJ
16h 32m
2 stops
$403Delta
Sat, Sep 5 - Mon, Sep 14
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
Delta Logo
6:05 am - 11:48 am
MDW
-
MBJ
5h 43m
1 stop
$403Delta
Mon, Sep 7 - Mon, Sep 14

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Delta flights from Montego Bay to Chicago Midway Airport

Our best Delta deals on Montego Bay to Chicago Midway Airport flight tickets
Delta
Sep 17
MBJ1:14 pmMontego Bay Sangster Intl
9h 31m
1 stop
MDW10:45 pmChicago Midway
Sep 22
MDW6:05 amChicago Midway
5h 43m
1 stop
MBJ11:48 amMontego Bay Sangster Intl
$397
Delta
Sep 7
MBJ1:09 pmMontego Bay Sangster Intl
9h 27m
1 stop
MDW10:36 pmChicago Midway
Sep 18
MDW7:01 pmChicago Midway
16h 32m
2 stops
MBJ11:33 amMontego Bay Sangster Intl
$403
Delta
Aug 22
MBJ2:26 pmMontego Bay Sangster Intl
8h 10m
1 stop
MDW10:36 pmChicago Midway
Aug 24
MDW6:05 amChicago Midway
9h 29m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
$531

Southwest flights from Montego Bay to Chicago Midway Airport

Our best Southwest deals on Montego Bay to Chicago Midway Airport flight tickets
Southwest
Sep 12
MBJ1:50 pmMontego Bay Sangster Intl
7h 10m
1 stop
MDW9:00 pmChicago Midway
Sep 19
MDW5:55 amChicago Midway
6h 30m
1 stop
MBJ12:25 pmMontego Bay Sangster Intl
$408
Southwest
Sep 17
MBJ2:15 pmMontego Bay Sangster Intl
8h 10m
2 stops
MDW10:25 pmChicago Midway
Sep 22
MDW6:30 amChicago Midway
6h 25m
1 stop
MBJ12:55 pmMontego Bay Sangster Intl
$444
Southwest
Sep 13
MBJ2:00 pmMontego Bay Sangster Intl
8h 30m
1 stop
MDW10:30 pmChicago Midway
Sep 20
MDW5:00 amChicago Midway
8h 00m
1 stop
MBJ1:00 pmMontego Bay Sangster Intl
$446

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 July 31, 2026.
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

Cheapest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 9/17

1:14 pm-10:45 pm

1 stop9h 31m

Chicago Midway

Tue 9/22

6:05 am-11:48 am

1 stop5h 43m

$397

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 9/2

2:26 pm-10:36 pm

1 stop8h 10m

Chicago Midway

Mon 9/14

9:59 am-11:33 am

2 stops25h 34m

$403

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 9/5

4:59 pm-9:17 am

2 stops16h 18m

Chicago Midway

Sat 9/19

6:40 pm-11:48 am

2 stops17h 08m

$403

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 9/2

1:09 pm-10:36 pm

1 stop9h 27m

Chicago Midway

Sat 9/19

6:40 pm-3:35 pm

2 stops20h 55m

$403

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 9/7

1:09 pm-9:07 am

2 stops19h 58m

Chicago Midway

Mon 9/14

7:01 pm-11:33 am

2 stops16h 32m

$403

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 9/4

2:26 pm-9:17 am

2 stops18h 51m

Chicago Midway

Fri 9/18

7:01 pm-11:33 am

2 stops16h 32m

$403

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 9/5

4:59 pm-9:17 am

2 stops16h 18m

Chicago Midway

Sun 9/20

7:01 pm-11:48 am

2 stops16h 47m

$403

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 9/2

1:09 pm-10:36 pm

1 stop9h 27m

Chicago Midway

Sun 9/20

7:01 pm-11:48 am

2 stops16h 47m

$403

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 9/5

4:59 pm-9:17 am

2 stops16h 18m

Chicago Midway

Mon 9/14

7:01 pm-11:33 am

2 stops16h 32m

$403
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 9/7

1:09 pm-10:36 pm

1 stop9h 27m

Chicago Midway

Mon 9/14

6:05 am-11:48 am

1 stop5h 43m

$403

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Chicago from

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 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 $473 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 to Chicago Midway Airport flights?

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

No. A direct flight is the cheapest option for a flight between Montego Bay to Chicago Midway Airport.

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

7h 10m

Direct flights

Sun
The fastest flight from Montego Bay to Chicago Midway Airport takes 7h 10m
Direct flights go from Montego Bay to Chicago Midway Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

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

  • 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 7h 10m.

  • 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 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?

Traveling to a place near Chicago?

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