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Cheap flights from Montego Bay to Chicago from $199

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 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Montego Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:58 pm - 11:47 pmMBJ-MDW
6h 49m1 stop
Delta Logo
6:00 am - 4:33 pmMDW-MBJ
9h 33m1 stop
$326Delta
Find Deal
qua, dez 3 - sex, dez 5
Multiple Airlines Logo
5:06 pm - 11:25 pmMBJ-MDW
7h 19m1 stop
Multiple Airlines Logo
2:01 pm - 12:05 pmMDW-MBJ
21h 04m2 stops
$385Multiple Airlines
Find Deal
sex, jan 9 - seg, jan 12
Delta Logo
4:45 pm - 10:09 pmMBJ-MDW
6h 24m1 stop
Delta Logo
6:45 am - 8:36 pmMDW-MBJ
12h 51m1 stop
$397Delta
Find Deal
sex, jan 9 - seg, jan 12
Frontier Logo
2:43 pm - 10:43 pmMBJ-MDW
9h 00m1 stop
Frontier Logo
6:05 am - 3:35 pmMDW-MBJ
8h 30m1 stop
$456Frontier
Find Deal
qui, nov 20 - dom, nov 23
Delta Logo
4:45 pm - 10:09 pmMBJ-MDW
6h 24m1 stop
Delta Logo
9:34 am - 8:36 pmMDW-MBJ
10h 02m2 stops
$566Delta
Find Deal
sex, jan 9 - seg, jan 12
Multiple Airlines Logo
5:06 pm - 11:25 pmMBJ-MDW
7h 19m1 stop
Multiple Airlines Logo
11:00 am - 11:15 amMDW-MBJ
23h 15m1 stop
$576Multiple Airlines
Find Deal
sex, jan 9 - seg, jan 12
Frontier Logo
5:06 pm - 10:12 pmMBJ-MDW
30h 06m1 stop
Frontier Logo
6:00 am - 2:54 pmMDW-MBJ
7h 54m1 stop
$807Frontier
Find Deal
dom, dez 14 - dom, dez 21
Frontier Logo
5:06 pm - 10:12 pmMBJ-MDW
30h 06m1 stop
Frontier Logo
10:50 pm - 9:09 amMDW-MBJ
57h 19m2 stops
$810Frontier
Find Deal
dom, dez 14 - dom, dez 21
WestJet Logo
8:25 pm - 10:34 amMBJ-MDW
15h 09m2 stops
WestJet Logo
11:21 am - 1:54 pmMDW-MBJ
25h 33m2 stops
$1,165WestJet
Find Deal
sex, jan 9 - seg, jan 12
WestJet Logo
8:25 pm - 10:34 amMBJ-MDW
15h 09m2 stops
WestJet Logo
11:21 am - 1:54 pmMDW-MBJ
25h 33m2 stops
$1,202WestJet
Find Deal
sex, jan 9 - seg, jan 12

Delta flights from Montego Bay to Chicago Midway Airport

Our best Delta deals on Montego Bay to Chicago Midway Airport flight tickets
Delta
Dec 3
MBJ5:58 pmMontego Bay Sangster Intl
6h 49m
1 stop
MDW11:47 pmChicago Midway
Dec 5
MDW6:00 amChicago Midway
9h 33m
1 stop
MBJ4:33 pmMontego Bay Sangster Intl
$326
Find similar
Delta
Jan 9
MBJ4:45 pmMontego Bay Sangster Intl
6h 24m
1 stop
MDW10:09 pmChicago Midway
Jan 12
MDW6:45 amChicago Midway
12h 51m
1 stop
MBJ8:36 pmMontego Bay Sangster Intl
$397
Find similar
Delta
Jan 9
MBJ4:45 pmMontego Bay Sangster Intl
6h 24m
1 stop
MDW10:09 pmChicago Midway
Jan 12
MDW9:34 amChicago Midway
10h 02m
2 stops
MBJ8:36 pmMontego Bay Sangster Intl
$566
Find similar

Frontier flights from Montego Bay to Chicago Midway Airport

Our best Frontier deals on Montego Bay to Chicago Midway Airport flight tickets
Frontier
Nov 20
MBJ2:43 pmMontego Bay Sangster Intl
9h 00m
1 stop
MDW10:43 pmChicago Midway
Nov 23
MDW6:05 amChicago Midway
8h 30m
1 stop
MBJ3:35 pmMontego Bay Sangster Intl
$456
Find similar
Frontier
Dec 14
MBJ5:06 pmMontego Bay Sangster Intl
30h 06m
1 stop
MDW10:12 pmChicago Midway
Dec 21
MDW6:00 amChicago Midway
7h 54m
1 stop
MBJ2:54 pmMontego Bay Sangster Intl
$807
Find similar
Frontier
Dec 14
MBJ5:06 pmMontego Bay Sangster Intl
30h 06m
1 stop
MDW10:12 pmChicago Midway
Dec 21
MDW10:50 pmChicago Midway
57h 19m
2 stops
MBJ9:09 amMontego Bay Sangster Intl
$810
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 outubro 31, 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

qua 12/3

5:58 pm-11:47 pm

1 stop6h 49m

Chicago Midway

sex 12/5

6:00 am-4:33 pm

1 stop9h 33m

$326

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sex 1/9

5:06 pm-11:25 pm

1 stop7h 19m

Chicago Midway

seg 1/12

2:01 pm-12:05 pm

2 stops21h 04m

$385

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sex 1/9

4:45 pm-10:09 pm

1 stop6h 24m

Chicago Midway

seg 1/12

6:45 am-8:36 pm

1 stop12h 51m

$397

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

qui 11/20

2:43 pm-10:43 pm

1 stop9h 00m

Chicago Midway

dom 11/23

6:05 am-3:35 pm

1 stop8h 30m

$456

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sex 1/9

4:45 pm-10:09 pm

1 stop6h 24m

Chicago Midway

seg 1/12

9:34 am-8:36 pm

2 stops10h 02m

$566

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sex 1/9

5:06 pm-11:25 pm

1 stop7h 19m

Chicago Midway

seg 1/12

11:00 am-11:15 am

1 stop23h 15m

$576

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

dom 12/14

5:06 pm-10:12 pm

1 stop30h 06m

Chicago Midway

dom 12/21

6:00 am-2:54 pm

1 stop7h 54m

$807

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

dom 12/14

5:06 pm-10:12 pm

1 stop30h 06m

Chicago Midway

dom 12/21

10:50 pm-9:09 am

2 stops57h 19m

$810

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sex 1/9

8:25 pm-10:34 am

2 stops15h 09m

Chicago Midway

seg 1/12

11:21 am-1:54 pm

2 stops25h 33m

$1,165

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sex 1/9

8:25 pm-10:34 am

2 stops15h 09m

Chicago Midway

seg 1/12

11:21 am-1:54 pm

2 stops25h 33m

$1,202

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 $532. 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 $549 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?

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

4h 10m

Direct flights

Mon and Sun
The fastest flight from Montego Bay to Chicago Midway Airport takes 4h 10m
Direct flights go from Montego Bay to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
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 6h 24m.

  • 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
4,241 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
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.

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dom 11/30
dom 12/7
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