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Cheap flights from Montego Bay to Chicago from $193

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 11/11. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Montego Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
United Airlines Logo
5:00 am - 2:14 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
8h 14m1 stop Newark
$324United Airlines
Wed, Nov 11 - Mon, Nov 16
United Airlines Logo
1:25 pm - 9:18 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
8h 53m1 stop Newark
United Airlines Logo
5:00 am - 2:14 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
8h 14m1 stop Newark
$334United Airlines
Wed, Nov 11 - Mon, Nov 16
Delta Logo
6:00 pm - 7:46 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
14h 46m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
7:00 am - 4:35 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
8h 35m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$337Delta
Wed, Nov 11 - Mon, Nov 16
Delta Logo
6:00 pm - 7:46 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
14h 46m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:45 am - 4:35 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
8h 50m1 stop Atlanta Hartsfield-Jackson
$337Delta
Wed, Nov 11 - Mon, Nov 16
Air Canada Logo
1:50 pm - 5:43 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
28h 53m1 stop Toronto Pearson Intl
Air Canada Logo
8:50 pm - 12:50 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
15h 00m1 stop Toronto Pearson Intl
$356Air Canada
Thu, Dec 3 - Tue, Dec 8
United Airlines Logo
3:20 pm - 11:49 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
9h 29m1 stop Newark
United Airlines Logo
8:40 am - 1:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
$356United Airlines
Mon, Nov 23 - Sun, Nov 29
United Airlines Logo
1:25 pm - 10:18 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
9h 53m1 stop Newark
United Airlines Logo
8:40 am - 1:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
$356United Airlines
Mon, Nov 23 - Sun, Nov 29
American Airlines Logo
2:12 pm - 6:55 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 43mnonstop
American Airlines Logo
9:00 am - 1:12 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 12mnonstop
$391American Airlines
Wed, Sep 2 - Tue, Sep 8
American Airlines Logo
3:12 pm - 6:59 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 47mnonstop
American Airlines Logo
8:11 am - 1:21 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 10mnonstop
$391American Airlines
Wed, Dec 16 - Mon, Jan 4
American Airlines Logo
3:57 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 49mnonstop
American Airlines Logo
9:40 am - 2:57 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 17mnonstop
$391American Airlines
Wed, Nov 11 - Mon, Nov 16

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American Airlines flights from Montego Bay to Chicago O'Hare Intl Airport

Our best American Airlines deals on Montego Bay to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 2
MBJ2:12 pmMontego Bay Sangster Intl
4h 43m
ORD6:55 pmChicago O'Hare Intl
Sep 8
ORD9:00 amChicago O'Hare Intl
4h 12m
MBJ1:12 pmMontego Bay Sangster Intl
$391
American Airlines
Sep 2
MBJ2:12 pmMontego Bay Sangster Intl
4h 43m
ORD6:55 pmChicago O'Hare Intl
Sep 8
ORD9:00 amChicago O'Hare Intl
4h 12m
MBJ1:12 pmMontego Bay Sangster Intl
$396
American Airlines
Sep 2
MBJ3:23 pmMontego Bay Sangster Intl
16h 07m
1 stop
ORD7:30 amChicago O'Hare Intl
Sep 8
ORD9:00 amChicago O'Hare Intl
4h 12m
MBJ1:12 pmMontego Bay Sangster Intl
$402

United Airlines flights from Montego Bay to Chicago O'Hare Intl Airport

Our best United Airlines deals on Montego Bay to Chicago O'Hare Intl Airport flight tickets
United Airlines
Nov 11
MBJ2:54 pmMontego Bay Sangster Intl
4h 26m
ORD6:20 pmChicago O'Hare Intl
Nov 16
ORD5:00 amChicago O'Hare Intl
8h 14m
1 stop
MBJ2:14 pmMontego Bay Sangster Intl
$324
United Airlines
Nov 11
MBJ1:25 pmMontego Bay Sangster Intl
8h 53m
1 stop
ORD9:18 pmChicago O'Hare Intl
Nov 16
ORD5:00 amChicago O'Hare Intl
8h 14m
1 stop
MBJ2:14 pmMontego Bay Sangster Intl
$334
United Airlines
Nov 23
MBJ1:25 pmMontego Bay Sangster Intl
9h 53m
1 stop
ORD10:18 pmChicago O'Hare Intl
Nov 29
ORD8:40 amChicago O'Hare Intl
4h 08m
MBJ1:48 pmMontego Bay Sangster Intl
$356

momondo Fare Finder

 
Customize your flight search to find flights from Montego Bay to Chicago O'Hare Intl 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 12, 2026.
Use the filters below to find and compare flights from Montego Bay to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 11/11

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Mon 11/16

5:00 am-2:14 pm

1 stop8h 14m

$324

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 11/11

1:25 pm-9:18 pm

1 stop8h 53m

Chicago O'Hare Intl

Mon 11/16

5:00 am-2:14 pm

1 stop8h 14m

$334

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 11/11

6:00 pm-7:46 am

2 stops14h 46m

Chicago O'Hare Intl

Mon 11/16

7:00 am-4:35 pm

2 stops8h 35m

$337

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 11/11

6:00 pm-7:46 am

2 stops14h 46m

Chicago O'Hare Intl

Mon 11/16

6:45 am-4:35 pm

1 stop8h 50m

$337

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Thu 12/3

1:50 pm-5:43 pm

1 stop28h 53m

Chicago O'Hare Intl

Tue 12/8

8:50 pm-12:50 pm

1 stop15h 00m

$356

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Mon 11/23

3:20 pm-11:49 pm

1 stop9h 29m

Chicago O'Hare Intl

Sun 11/29

8:40 am-1:48 pm

Nonstop4h 08m

$356

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Mon 11/23

1:25 pm-10:18 pm

1 stop9h 53m

Chicago O'Hare Intl

Sun 11/29

8:40 am-1:48 pm

Nonstop4h 08m

$356
Quickest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 9/2

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 9/8

9:00 am-1:12 pm

Nonstop4h 12m

$391

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 12/16

3:12 pm-6:59 pm

Nonstop4h 47m

Chicago O'Hare Intl

Mon 1/4

8:11 am-1:21 pm

Nonstop4h 10m

$391

Montego BayChicago

MBJ Montego Bay Sangster Intl - ORD Chicago O'Hare Intl

MBJORD

Montego Bay Sangster Intl

Wed 11/11

3:57 pm-7:46 pm

Nonstop4h 49m

Chicago O'Hare Intl

Mon 11/16

9:40 am-2:57 pm

Nonstop4h 17m

$391

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 O'Hare Intl 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 O'Hare Intl Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $399 to $590.
The lowest price recently found on this route was $324.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Montego Bay averaging around $348.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $413. This is often the case because there is less demand to fly during this day of the week. 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 $531.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Montego Bay in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $454 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $463. 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 O'Hare Intl flight route?

Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Montego Bay Sangster Intl - Chicago O'Hare Intl flight prices

What cabin class options are available on Montego Bay to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on Montego Bay to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Montego Bay to Chicago O'Hare Intl Airport.

How have Montego Bay to Chicago O'Hare Intl Airport flight prices changed over time?

As of August 2026, prices for Montego Bay to Chicago O'Hare Intl Airport flights are approximately 28% cheaper when compared to flights at the same time last year.

When to book flights from Montego Bay to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montego Bay to Chicago O'Hare Intl 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 O'Hare Intl Airport (MBJ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montego Bay to Chicago O'Hare Intl Airport

Best Price Found

$329

Fastest flight time

4h 26m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Montego Bay in the past 72 hours is $329. The best round-trip flight deal from Montego Bay to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $411.
The fastest flight from Montego Bay to Chicago O'Hare Intl Airport takes 4h 26m
Direct flights go from Montego Bay to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Montego Bay to Chicago O'Hare Intl Airport

  • How far is Montego Bay Sangster Intl to Chicago O'Hare Intl by plane?

    The distance between Montego Bay Sangster Intl and Chicago O'Hare Intl is about 1726.0 mi. A reasonable flight in good conditions will take 4h 26m.

  • When did momondo last update prices for flights from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl 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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Montego Bay to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Montego Bay to Chicago O'Hare Intl Airport?

Best airlines flying from Montego Bay to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Montego Bay to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $281Free CancellationRating
7.4
10,111 reviews
Search United Airlines flights
American AirlinesPriceFrom $281Free CancellationRating
7.1
11,911 reviews
Search American Airlines flights

  • American Airlines Flights From Montego Bay to Chicago O'Hare Intl Airport

    American Airlines flight deals from Montego Bay to Chicago O'Hare Intl Airport start from $281 round-trip. Over the 7 American Airlines flights for this route in a normal week, average airfare is usually $403 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Gurnee
Rosemont
Oak Brook
Orland Park
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Racine
Aurora
Janesville
Elgin
South Holland
Evanston

Why use momondo?

Why should I use momondo to find a flight deal from Montego Bay to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Montego Bay.

Can I find flights from Montego Bay to Chicago with flexible booking policies on momondo?

Flights from Montego Bay to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Montego Bay and alert you when they change.

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