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Cheap flights from Montego Bay to Chicago from $200

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 8/29. 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.
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
$455Frontier
Sat, Jul 4 - Sat, Jul 11
Frontier Logo
1:26 pm - 11:07 am
MBJ
-
MDW
21h 41m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$475Frontier
Sat, Jul 4 - Sun, Aug 30
Delta Logo
2:31 pm - 10:15 pm
MBJ
-
MDW
7h 44m
1 stop
Delta Logo
6:00 am - 3:34 pm
MDW
-
MBJ
9h 34m
1 stop
$487Delta
Tue, Jul 21 - Tue, Jul 28
Frontier Logo
1:26 pm - 10:11 pm
MBJ
-
MDW
8h 45m
1 stop
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
$506Frontier
Thu, Jun 25 - Mon, Jun 29
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
7:10 am - 2:25 pm
MDW
-
MBJ
7h 15m
1 stop
$527Southwest
Sat, Jul 4 - Sun, Aug 30
Southwest Logo
11:45 am - 9:25 pm
MBJ
-
MDW
9h 40m
1 stop
Southwest Logo
6:35 pm - 11:35 am
MDW
-
MBJ
17h 00m
2 stops
$531Southwest
Thu, Jun 25 - Mon, Jun 29
Southwest Logo
1:15 pm - 7:50 pm
MBJ
-
MDW
6h 35m
1 stop
Southwest Logo
5:55 am - 1:15 pm
MDW
-
MBJ
7h 20m
2 stops
$542Southwest
Sat, Jul 4 - Mon, Aug 31
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
Southwest Logo
6:30 am - 12:55 pm
MDW
-
MBJ
6h 25m
1 stop
$544Southwest
Sat, Jul 4 - Tue, Sep 1
Southwest Logo
1:15 pm - 7:50 pm
MBJ
-
MDW
6h 35m
1 stop
Southwest Logo
5:00 am - 1:30 pm
MDW
-
MBJ
8h 30m
2 stops
$552Southwest
Sat, Jul 4 - Sun, Aug 30
Southwest Logo
12:15 pm - 10:20 pm
MBJ
-
MDW
10h 05m
2 stops
Southwest Logo
5:00 am - 1:15 pm
MDW
-
MBJ
8h 15m
1 stop
$559Southwest
Fri, Sep 11 - Thu, Sep 17

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Frontier flights from Montego Bay to Chicago Midway Airport

Our best Frontier deals on Montego Bay to Chicago Midway Airport flight tickets
Frontier
Jul 4
MBJ1:26 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW10:11 pmChicago Midway
Jul 11
MDW6:05 amChicago Midway
6h 22m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
$455
Frontier
Jul 4
MBJ1:26 pmMontego Bay Sangster Intl
21h 41m
1 stop
MDW11:07 amChicago Midway
Aug 30
MDW6:00 amChicago Midway
6h 21m
1 stop
MBJ12:21 pmMontego Bay Sangster Intl
$475
Frontier
Jun 25
MBJ1:26 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW10:11 pmChicago Midway
Jun 29
MDW6:00 amChicago Midway
6h 21m
1 stop
MBJ12:21 pmMontego Bay Sangster Intl
$506

Southwest flights from Montego Bay to Chicago Midway Airport

Our best Southwest deals on Montego Bay to Chicago Midway Airport flight tickets
Southwest
Jul 4
MBJ2:30 pmMontego Bay Sangster Intl
4h 05m
MDW6:35 pmChicago Midway
Sep 1
MDW6:15 amChicago Midway
5h 40m
1 stop
MBJ11:55 amMontego Bay Sangster Intl
$527
Southwest
Jun 25
MBJ11:45 amMontego Bay Sangster Intl
9h 40m
1 stop
MDW9:25 pmChicago Midway
Jun 29
MDW6:35 pmChicago Midway
17h 00m
2 stops
MBJ11:35 amMontego Bay Sangster Intl
$531
Southwest
Jul 4
MBJ1:15 pmMontego Bay Sangster Intl
6h 35m
1 stop
MDW7:50 pmChicago Midway
Aug 31
MDW5:55 amChicago Midway
7h 20m
2 stops
MBJ1:15 pmMontego Bay Sangster Intl
$542

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 June 8, 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

Sat 7/4

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sat 7/11

6:05 am-12:27 pm

1 stop6h 22m

$455

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

1:26 pm-11:07 am

1 stop21h 41m

Chicago Midway

Sun 8/30

6:00 am-12:21 pm

1 stop6h 21m

$475

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 7/21

2:31 pm-10:15 pm

1 stop7h 44m

Chicago Midway

Tue 7/28

6:00 am-3:34 pm

1 stop9h 34m

$487

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 6/25

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Mon 6/29

6:00 am-12:21 pm

1 stop6h 21m

$506

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

Chicago Midway

Sun 8/30

7:10 am-2:25 pm

1 stop7h 15m

$527

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 6/25

11:45 am-9:25 pm

1 stop9h 40m

Chicago Midway

Mon 6/29

6:35 pm-11:35 am

2 stops17h 00m

$531

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

1:15 pm-7:50 pm

1 stop6h 35m

Chicago Midway

Mon 8/31

5:55 am-1:15 pm

2 stops7h 20m

$542
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

Chicago Midway

Tue 9/1

6:30 am-12:55 pm

1 stop6h 25m

$544

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 7/4

1:15 pm-7:50 pm

1 stop6h 35m

Chicago Midway

Sun 8/30

5:00 am-1:30 pm

2 stops8h 30m

$552

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 9/11

12:15 pm-10:20 pm

2 stops10h 05m

Chicago Midway

Thu 9/17

5:00 am-1:15 pm

1 stop8h 15m

$559

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 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 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 $463. 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 $543 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

8h 45m

Direct flights

Sun
The fastest flight from Montego Bay to Chicago Midway Airport takes 8h 45m
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 8h 45m.

  • 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
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Munster
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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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