Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Montego Bay to Chicago from $158

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 5/5. 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

Enter your travel dates to find the best prices.
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$226Frontier
Wed, May 6 - Wed, May 13
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$272Frontier
Tue, May 5 - Tue, May 19
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
$328Southwest
Thu, Jul 30 - Mon, Aug 3
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
$356Frontier
Wed, Jun 24 - Tue, Jul 7
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
5:10 am - 10:45 am
MDW
-
MBJ
5h 35m
1 stop
$373Southwest
Thu, Jul 30 - Mon, Aug 3
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
$376Frontier
Wed, Jun 24 - Sun, Jul 12
Frontier Logo
1:16 pm - 10:02 pm
MBJ
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:11 pm
MDW
-
MBJ
6h 11m
1 stop
$385Frontier
Wed, May 20 - Wed, May 27
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
$395Frontier
Thu, Jul 30 - Mon, Aug 3
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
$396Frontier
Tue, Jun 23 - Sat, Jul 11
Delta Logo
1:21 pm - 10:17 pm
MBJ
-
MDW
8h 56m
1 stop
Delta Logo
6:58 pm - 3:34 pm
MDW
-
MBJ
20h 36m
2 stops
$414Delta
Wed, Jun 24 - Mon, Jul 6

Frontier flights from Montego Bay to Chicago Midway Airport

Our best Frontier deals on Montego Bay to Chicago Midway Airport flight tickets
Frontier
May 6
MBJ1:16 pmMontego Bay Sangster Intl
8h 46m
1 stop
MDW10:02 pmChicago Midway
May 13
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
$226
Frontier
May 5
MBJ1:16 pmMontego Bay Sangster Intl
8h 46m
1 stop
MDW10:02 pmChicago Midway
May 19
MDW6:00 amChicago Midway
6h 11m
1 stop
MBJ12:11 pmMontego Bay Sangster Intl
$272
Frontier
Jun 24
MBJ1:26 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW10:11 pmChicago Midway
Jul 7
MDW6:00 amChicago Midway
6h 21m
1 stop
MBJ12:21 pmMontego Bay Sangster Intl
$356

Delta flights from Montego Bay to Chicago Midway Airport

Our best Delta deals on Montego Bay to Chicago Midway Airport flight tickets
Delta
Jun 24
MBJ1:21 pmMontego Bay Sangster Intl
8h 56m
1 stop
MDW10:17 pmChicago Midway
Jul 6
MDW6:58 pmChicago Midway
20h 36m
2 stops
MBJ3:34 pmMontego Bay Sangster Intl
$414
Delta
Sep 15
MBJ1:25 pmMontego Bay Sangster Intl
8h 21m
1 stop
MDW9:46 pmChicago Midway
Sep 19
MDW6:00 amChicago Midway
9h 34m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
$442
Delta
Jun 25
MBJ4:59 pmMontego Bay Sangster Intl
16h 15m
2 stops
MDW9:14 amChicago Midway
Jul 11
MDW6:35 pmChicago Midway
18h 31m
2 stops
MBJ1:06 pmMontego Bay Sangster Intl
$450

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 April 9, 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

Wed 5/6

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Wed 5/13

6:00 am-12:11 pm

1 stop6h 11m

$226

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 5/5

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Tue 5/19

6:00 am-12:11 pm

1 stop6h 11m

$272
Quickest round-trip

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 7/30

1:50 pm-5:50 pm

Nonstop4h 00m

Chicago Midway

Mon 8/3

10:05 am-1:55 pm

Nonstop3h 50m

$328

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/24

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Tue 7/7

6:00 am-12:21 pm

1 stop6h 21m

$356

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 7/30

1:50 pm-5:50 pm

Nonstop4h 00m

Chicago Midway

Mon 8/3

5:10 am-10:45 am

1 stop5h 35m

$373

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/24

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sun 7/12

6:00 am-12:21 pm

1 stop6h 21m

$376

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 5/20

1:16 pm-10:02 pm

1 stop8h 46m

Chicago Midway

Wed 5/27

6:00 am-12:11 pm

1 stop6h 11m

$385

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 7/30

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Mon 8/3

6:00 am-12:21 pm

1 stop6h 21m

$395

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 6/23

1:26 pm-10:11 pm

1 stop8h 45m

Chicago Midway

Sat 7/11

6:00 am-12:21 pm

1 stop6h 21m

$396

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 6/24

1:21 pm-10:17 pm

1 stop8h 56m

Chicago Midway

Mon 7/6

6:58 pm-3:34 pm

2 stops20h 36m

$414

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 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 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 11% 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

$462

Fastest flight time

4h 00m

Direct flights

Mon, Tue, Wed, Fri and Sun
The best flight deal from Montego Bay to Chicago Midway Airport found on momondo in the last 72 hours is $462
The fastest flight from Montego Bay to Chicago Midway Airport takes 4h 00m
Direct flights go from Montego Bay to Chicago Midway Airport on Monday, Tuesday, Wednesday, Friday and 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 4h 00m.

  • 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
4,338 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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
Sat 5/9
Sat 5/16
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago