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Cheap flights from Montego Bay to Chicago from $209

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.
Air Canada Logo
1:50 pm - 1:13 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
24h 23m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 am - 5:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 35m1 stop Toronto Pearson Intl
$370Air Canada
Wed, Nov 11 - Mon, Nov 16
Air Canada Logo
1:50 pm - 9:23 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 33m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 am - 5:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 35m1 stop Toronto Pearson Intl
$371Air Canada
Thu, Nov 26 - Mon, Nov 30
Air Canada Logo
1:50 pm - 9:08 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 18m1 stop Toronto Pearson Intl
Air Canada Logo
4:30 pm - 5:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
23h 50m1 stop Toronto Pearson Intl
$371Air Canada
Tue, Dec 1 - Tue, Dec 8
Air Canada Logo
1:50 pm - 9:23 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 33m1 stop Toronto Pearson Intl
Air Canada Logo
1:55 pm - 1:25 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
22h 30m1 stop Montreal Pierre Elliott Trudeau Intl
$387Air Canada
Sat, Nov 7 - Sat, Nov 14
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
United Airlines Logo
8:40 am - 1:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
$432United Airlines
Tue, Dec 15 - Sun, Jan 3
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
United Airlines Logo
7:04 am - 4:19 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
8h 15m1 stop Washington, D.C. Dulles Intl
$436United Airlines
Tue, Dec 15 - Sun, Jan 3
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
United Airlines Logo
8:40 am - 1:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
$445United Airlines
Thu, Nov 5 - Mon, Nov 9
American Airlines Logo
3:56 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 50mnonstop
American Airlines Logo
9:40 am - 2:52 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 12mnonstop
$446American Airlines
Wed, Nov 11 - Mon, Nov 16
American Airlines Logo
6:12 pm - 9:30 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
16h 18m1 stop Miami
American Airlines Logo
5:21 am - 2:22 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
8h 01m1 stop Charlotte Douglas
$446American Airlines
Tue, Dec 15 - Sun, Jan 3
American Airlines Logo
3:56 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 50mnonstop
American Airlines Logo
6:00 am - 5:09 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
10h 09m1 stop Dallas/Fort Worth
$450American Airlines
Wed, Nov 11 - Mon, Nov 16

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Air Canada flights from Montego Bay to Chicago O'Hare Intl Airport

Our best Air Canada deals on Montego Bay to Chicago O'Hare Intl Airport flight tickets
Air Canada
Nov 11
MBJ1:50 pmMontego Bay Sangster Intl
24h 23m
1 stop
ORD1:13 pmChicago O'Hare Intl
Nov 16
ORD8:45 amChicago O'Hare Intl
7h 35m
1 stop
MBJ5:20 pmMontego Bay Sangster Intl
$370
Air Canada
Nov 26
MBJ1:50 pmMontego Bay Sangster Intl
20h 33m
1 stop
ORD9:23 amChicago O'Hare Intl
Nov 30
ORD8:45 amChicago O'Hare Intl
7h 35m
1 stop
MBJ5:20 pmMontego Bay Sangster Intl
$371
Air Canada
Nov 7
MBJ1:50 pmMontego Bay Sangster Intl
20h 33m
1 stop
ORD9:23 amChicago O'Hare Intl
Nov 14
ORD1:55 pmChicago O'Hare Intl
22h 30m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
$387

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
Dec 15
MBJ2:54 pmMontego Bay Sangster Intl
4h 26m
ORD6:20 pmChicago O'Hare Intl
Jan 3
ORD8:40 amChicago O'Hare Intl
4h 08m
MBJ1:48 pmMontego Bay Sangster Intl
$432
United Airlines
Nov 2
MBJ2:54 pmMontego Bay Sangster Intl
4h 26m
ORD6:20 pmChicago O'Hare Intl
Nov 10
ORD8:40 amChicago O'Hare Intl
4h 08m
MBJ1:48 pmMontego Bay Sangster Intl
$445
United Airlines
Nov 2
MBJ2:54 pmMontego Bay Sangster Intl
4h 26m
ORD6:20 pmChicago O'Hare Intl
Nov 9
ORD8:40 pmChicago O'Hare Intl
14h 33m
1 stop
MBJ12:13 pmMontego Bay Sangster Intl
$449

momondo Fare Finder

 
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

1:50 pm-1:13 pm

1 stop24h 23m

Chicago O'Hare Intl

Mon 11/16

8:45 am-5:20 pm

1 stop7h 35m

$370

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Thu 11/26

1:50 pm-9:23 am

1 stop20h 33m

Chicago O'Hare Intl

Mon 11/30

8:45 am-5:20 pm

1 stop7h 35m

$371

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 12/1

1:50 pm-9:08 am

1 stop20h 18m

Chicago O'Hare Intl

Tue 12/8

4:30 pm-5:20 pm

1 stop23h 50m

$371

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Sat 11/7

1:50 pm-9:23 am

1 stop20h 33m

Chicago O'Hare Intl

Sat 11/14

1:55 pm-1:25 pm

1 stop22h 30m

$387
Quickest round-trip

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 12/15

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Sun 1/3

8:40 am-1:48 pm

Nonstop4h 08m

$432

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 12/15

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Sun 1/3

7:04 am-4:19 pm

1 stop8h 15m

$436

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Thu 11/5

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Mon 11/9

8:40 am-1:48 pm

Nonstop4h 08m

$445

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Wed 11/11

3:56 pm-7:46 pm

Nonstop4h 50m

Chicago O'Hare Intl

Mon 11/16

9:40 am-2:52 pm

Nonstop4h 12m

$446

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 12/15

6:12 pm-9:30 am

1 stop16h 18m

Chicago O'Hare Intl

Sun 1/3

5:21 am-2:22 pm

1 stop8h 01m

$446

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Wed 11/11

3:56 pm-7:46 pm

Nonstop4h 50m

Chicago O'Hare Intl

Mon 11/16

6:00 am-5:09 pm

1 stop10h 09m

$450

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 $406 to $512.
The lowest price recently found on this route was $370.

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

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Montego Bay averaging around $300.

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 Thursday when prices can be found for as low as $416. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday 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 $548.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $469 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $486. 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?

You could potentially save up to 12% on your flight if you consider stops on a Montego Bay to Chicago O'Hare Intl Airport flight.

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

As of October 2026, prices for Montego Bay to Chicago O'Hare Intl Airport flights are approximately 5% more expensive 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

$209

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 $209. The best round-trip flight deal from Montego Bay to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $370.
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
7.3
10,404 reviews
Search United Airlines flights
American AirlinesPriceFrom $281Free CancellationRating
7.0
12,186 reviews
Search American Airlines flights

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
Rosemont
Oak Brook
Gurnee
Joliet
Orland Park
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Waukegan
Skokie

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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