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Cheap flights from Montego Bay to Chicago from $224

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
4:23 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 24m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:16 am - 3:29 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 13m1 stop Atlanta Hartsfield-Jackson
$368Frontier
Mon, Nov 2 - Sun, Nov 8
Frontier Logo
3:23 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 24m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:42 pm - 3:29 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 47m1 stop Atlanta Hartsfield-Jackson
$497Frontier
Fri, Oct 30 - Wed, Nov 4
Southwest Logo
1:00 pm - 11:05 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
11h 05m1 stop Baltimore/Washington
Southwest Logo
5:00 am - 2:30 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 30m1 stop Orlando
$504Southwest
Fri, Nov 20 - Sat, Dec 12
Southwest Logo
1:50 pm - 11:05 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
10h 15m2 stops Orlando Baltimore/Washington
Southwest Logo
5:00 am - 2:30 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 30m1 stop Orlando
$552Southwest
Fri, Nov 20 - Sat, Dec 12
Southwest Logo
2:25 pm - 5:35 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
4h 10mnonstop
Southwest Logo
8:35 pm - 2:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 50m2 stops Orlando Baltimore/Washington
$604Southwest
Sat, Dec 19 - Mon, Dec 28
Southwest Logo
12:00 pm - 10:15 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
10h 15m2 stops Orlando Nashville Intl
Southwest Logo
8:40 pm - 2:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 45m2 stops Orlando Baltimore/Washington
$618Southwest
Wed, Oct 14 - Thu, Nov 12
Southwest Logo
12:50 pm - 9:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 35m1 stop Baltimore/Washington
Southwest Logo
8:40 pm - 2:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 45m2 stops Orlando Baltimore/Washington
$653Southwest
Wed, Oct 14 - Thu, Nov 12
Frontier Logo
2:25 pm - 7:01 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
17h 36m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:07 pm - 1:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 01m2 stops Orlando Atlanta Hartsfield-Jackson
$656Frontier
Sat, Dec 19 - Mon, Dec 28
Southwest Logo
2:50 pm - 12:20 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
10h 30m2 stops Orlando Nashville Intl
Southwest Logo
9:05 pm - 2:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
16h 40m2 stops Baltimore/Washington Orlando
$687Southwest
Sat, Dec 19 - Mon, Dec 28
Southwest Logo
12:50 pm - 9:25 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 35m1 stop Baltimore/Washington
Southwest Logo
7:00 am - 2:45 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 45m1 stop Orlando
$742Southwest
Wed, Oct 14 - Thu, Nov 12

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Southwest flights from Montego Bay to Chicago Midway Airport

Our best Southwest deals on Montego Bay to Chicago Midway Airport flight tickets
Southwest
Nov 20
MBJ1:00 pmMontego Bay Sangster Intl
11h 05m
1 stop
MDW11:05 pmChicago Midway
Dec 12
MDW5:00 amChicago Midway
8h 30m
1 stop
MBJ2:30 pmMontego Bay Sangster Intl
$504
Southwest
Nov 20
MBJ1:50 pmMontego Bay Sangster Intl
10h 15m
2 stops
MDW11:05 pmChicago Midway
Dec 12
MDW5:00 amChicago Midway
8h 30m
1 stop
MBJ2:30 pmMontego Bay Sangster Intl
$552
Southwest
Oct 14
MBJ12:00 pmMontego Bay Sangster Intl
10h 15m
2 stops
MDW10:15 pmChicago Midway
Nov 12
MDW8:40 pmChicago Midway
16h 45m
2 stops
MBJ2:25 pmMontego Bay Sangster Intl
$618

momondo Fare Finder

 
Use the filters below to find and compare flights from Montego Bay to Chicago Midway Airport that are best for you.

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Price

Cheapest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Mon 11/2

4:23 pm-11:47 pm

1 stop8h 24m

Chicago Midway

Sun 11/8

6:16 am-3:29 pm

1 stop8h 13m

$368

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Fri 10/30

3:23 pm-11:47 pm

1 stop8h 24m

Chicago Midway

Wed 11/4

6:42 pm-3:29 pm

1 stop19h 47m

$497

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Fri 11/20

1:00 pm-11:05 pm

1 stop11h 05m

Chicago Midway

Sat 12/12

5:00 am-2:30 pm

1 stop8h 30m

$504

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Fri 11/20

1:50 pm-11:05 pm

2 stops10h 15m

Chicago Midway

Sat 12/12

5:00 am-2:30 pm

1 stop8h 30m

$552

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Sat 12/19

2:25 pm-5:35 pm

Nonstop4h 10m

Chicago Midway

Mon 12/28

8:35 pm-2:25 pm

2 stops16h 50m

$604

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Wed 10/14

12:00 pm-10:15 pm

2 stops10h 15m

Chicago Midway

Thu 11/12

8:40 pm-2:25 pm

2 stops16h 45m

$618

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Wed 10/14

12:50 pm-9:25 pm

1 stop8h 35m

Chicago Midway

Thu 11/12

8:40 pm-2:25 pm

2 stops16h 45m

$653

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Sat 12/19

2:25 pm-7:01 am

1 stop17h 36m

Chicago Midway

Mon 12/28

8:07 pm-1:08 pm

2 stops16h 01m

$656

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Sat 12/19

2:50 pm-12:20 am

2 stops10h 30m

Chicago Midway

Mon 12/28

9:05 pm-2:45 pm

2 stops16h 40m

$687
Quickest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Wed 10/14

12:50 pm-9:25 pm

1 stop8h 35m

Chicago Midway

Thu 11/12

7:00 am-2:45 pm

1 stop6h 45m

$742

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 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?

You could potentially save up to 31% 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

Best Price Found

$224

Fastest flight time

10h 15m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Montego Bay in the past 72 hours is $224. The best round-trip flight deal from Montego Bay to Chicago Midway Airport found on momondo in the last 72 hours is $368.
The fastest flight from Montego Bay to Chicago Midway Airport takes 10h 15m
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 10h 15m.

  • 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 $281Free CancellationRating
8.0
4,191 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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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