Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Montego Bay to Chicago from $215

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 9/4. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Montego Bay to Chicago

Cheap round-trip flights

Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
$334Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$352Frontier
Find Deal
Sun, Sep 14 - Sun, Sep 21
Frontier Logo
9:05 am - 11:17 pmMBJ-MDW
14h 12m1 stop
Frontier Logo
11:03 am - 7:55 amMDW-MBJ
20h 52m1 stop
$362Frontier
Find Deal
Thu, Aug 14 - Thu, Aug 21
Frontier Logo
2:12 pm - 11:20 pmMBJ-MDW
9h 08m1 stop
Frontier Logo
9:00 am - 12:45 pmMDW-MBJ
27h 45m1 stop
$375Frontier
Find Deal
Fri, Sep 19 - Wed, Oct 1
Frontier Logo
9:05 am - 1:47 pmMBJ-MDW
28h 42m1 stop
Frontier Logo
6:20 am - 12:41 pmMDW-MBJ
6h 21m1 stop
$385Frontier
Find Deal
Wed, Aug 13 - Sun, Sep 7
Delta Logo
2:30 pm - 9:44 pmMBJ-MDW
7h 14m1 stop
Delta Logo
6:04 am - 3:38 pmMDW-MBJ
9h 34m1 stop
$497Delta
Find Deal
Wed, Aug 20 - Sun, Aug 24
Southwest Logo
12:55 pm - 10:25 pmMBJ-MDW
9h 30m2 stops
Southwest Logo
8:15 am - 2:00 pmMDW-MBJ
5h 45m1 stop
$594Southwest
Find Deal
Wed, Aug 20 - Sun, Aug 24
Southwest Logo
12:55 pm - 10:25 pmMBJ-MDW
9h 30m2 stops
Southwest Logo
5:35 am - 2:00 pmMDW-MBJ
8h 25m2 stops
$685Southwest
Find Deal
Wed, Aug 20 - Sun, Aug 24
WestJet Logo
12:45 pm - 1:03 pmMBJ-MDW
24h 18m2 stops
WestJet Logo
12:43 pm - 9:26 amMDW-MBJ
20h 43m2 stops
$1,242WestJet
Find Deal
Sun, Sep 14 - Sun, Sep 21
WestJet Logo
10:30 am - 9:44 pmMBJ-MDW
35h 14m2 stops
WestJet Logo
12:43 pm - 9:27 amMDW-MBJ
44h 44m2 stops
$1,315WestJet
Find Deal
Thu, Aug 14 - Thu, Aug 21

Frontier flights from Montego Bay to Chicago Midway Airport

Our best Frontier deals on Montego Bay to Chicago Midway Airport flight tickets
Frontier
Oct 2
MBJ2:12 pmMontego Bay Sangster Intl
9h 08m
1 stop
MDW11:20 pmChicago Midway
Oct 6
MDW6:20 amChicago Midway
6h 25m
1 stop
MBJ12:45 pmMontego Bay Sangster Intl
$334
Find similar
Frontier
Sep 14
MBJ2:12 pmMontego Bay Sangster Intl
9h 08m
1 stop
MDW11:20 pmChicago Midway
Sep 21
MDW6:20 amChicago Midway
6h 21m
1 stop
MBJ12:41 pmMontego Bay Sangster Intl
$352
Find similar
Frontier
Aug 14
MBJ9:05 amMontego Bay Sangster Intl
14h 12m
1 stop
MDW11:17 pmChicago Midway
Aug 21
MDW11:03 amChicago Midway
20h 52m
1 stop
MBJ7:55 amMontego Bay Sangster Intl
$362
Find similar

Delta flights from Montego Bay to Chicago Midway Airport

Our best Delta deals on Montego Bay to Chicago Midway Airport flight tickets
Delta
Aug 20
MBJ2:30 pmMontego Bay Sangster Intl
7h 14m
1 stop
MDW9:44 pmChicago Midway
Aug 24
MDW6:04 amChicago Midway
9h 34m
1 stop
MBJ3:38 pmMontego Bay Sangster Intl
$497
Find similar
Delta
Aug 3
MBJ12:49 pmMontego Bay Sangster Intl
19h 55m
2 stops
MDW8:44 amChicago Midway
Aug 11
MDW9:31 amChicago Midway
27h 34m
2 stops
MBJ1:05 pmMontego Bay Sangster Intl
$620
Find similar
Delta
Aug 3
MBJ12:49 pmMontego Bay Sangster Intl
19h 55m
2 stops
MDW8:44 amChicago Midway
Aug 9
MDW5:53 pmChicago Midway
21h 41m
2 stops
MBJ3:34 pmMontego Bay Sangster Intl
$646
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 August 2, 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

Thu 10/2

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Mon 10/6

6:20 am-12:45 pm

1 stop6h 25m

$334

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 9/14

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Sun 9/21

6:20 am-12:41 pm

1 stop6h 21m

$352

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 8/14

9:05 am-11:17 pm

1 stop14h 12m

Chicago Midway

Thu 8/21

11:03 am-7:55 am

1 stop20h 52m

$362

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 9/19

2:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Wed 10/1

9:00 am-12:45 pm

1 stop27h 45m

$375

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/13

9:05 am-1:47 pm

1 stop28h 42m

Chicago Midway

Sun 9/7

6:20 am-12:41 pm

1 stop6h 21m

$385

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/20

2:30 pm-9:44 pm

1 stop7h 14m

Chicago Midway

Sun 8/24

6:04 am-3:38 pm

1 stop9h 34m

$497

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/20

12:55 pm-10:25 pm

2 stops9h 30m

Chicago Midway

Sun 8/24

8:15 am-2:00 pm

1 stop5h 45m

$594

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 8/20

12:55 pm-10:25 pm

2 stops9h 30m

Chicago Midway

Sun 8/24

5:35 am-2:00 pm

2 stops8h 25m

$685

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 9/14

12:45 pm-1:03 pm

2 stops24h 18m

Chicago Midway

Sun 9/21

12:43 pm-9:26 am

2 stops20h 43m

$1,242

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 8/14

10:30 am-9:44 pm

2 stops35h 14m

Chicago Midway

Thu 8/21

12:43 pm-9:27 am

2 stops44h 44m

$1,315

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Montego Bay and Chicago Midway Airport?

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Montego Bay. The lowest ticket price found for a Thursday departure recently was $629. 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, Saturday 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 $743.

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 $568 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 are 1 cabin classes 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 25% 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

$215

Fastest flight time

4h 10m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Montego Bay in the past 72 hours is $215. The best round-trip flight deal from Montego Bay to Chicago Midway Airport found on momondo in the last 72 hours is $334.
The fastest flight from Montego Bay to Chicago Midway Airport takes 4h 10m
Direct flights go from Montego Bay to Chicago Midway Airport on Sunday. The only airline offering direct flights is Southwest.
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 7h 14m.

  • 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
4,246 reviews
Search Southwest flights

  • Southwest Flights From Montego Bay to Chicago Midway Airport

    Southwest operates around 3 flights from Montego Bay to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $550, 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 4,246 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
Schererville
Valparaiso
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 8/7
Thu 8/14
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago