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Cheap flights from Montego Bay to Chicago from $155

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 2/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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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.
American Airlines Logo
2:23 pm - 7:00 pm
MBJ
-
ORD
4h 37mnonstop
American Airlines Logo
6:25 pm - 9:25 am
ORD
-
MBJ
15h 00m1 stop
$470American Airlines
Sat, Jun 13 - Sat, Sep 5
American Airlines Logo
3:05 pm - 10:49 pm
MBJ
-
ORD
7h 44m1 stop
American Airlines Logo
8:34 pm - 9:25 am
ORD
-
MBJ
12h 51m1 stop
$480American Airlines
Sat, Jun 13 - Sat, Sep 5
Multiple Airlines Logo
12:15 pm - 1:25 pm
MBJ
-
ORD
25h 10m1 stop
Multiple Airlines Logo
9:30 am - 9:39 am
ORD
-
MBJ
24h 09m2 stops
$519Multiple Airlines
Sat, Jun 13 - Sat, Sep 5
Air Canada Logo
1:30 pm - 1:01 pm
MBJ
-
ORD
24h 31m1 stop
Air Canada Logo
10:00 am - 12:30 pm
ORD
-
MBJ
25h 30m1 stop
$541Air Canada
Wed, Jan 7 - Wed, Jan 14
Air Canada Logo
1:30 pm - 8:10 pm
MBJ
-
ORD
31h 40m2 stops
Air Canada Logo
6:00 pm - 12:30 pm
ORD
-
MBJ
17h 30m2 stops
$554Air Canada
Wed, Jan 7 - Wed, Jan 14
American Airlines Logo
2:23 pm - 7:00 pm
MBJ
-
ORD
4h 37mnonstop
American Airlines Logo
8:30 am - 12:31 pm
ORD
-
MBJ
4h 01mnonstop
$578American Airlines
Sat, Jun 13 - Sat, Sep 5
Multiple Airlines Logo
12:15 pm - 8:08 pm
MBJ
-
ORD
31h 53m2 stops
Multiple Airlines Logo
9:30 am - 1:10 pm
ORD
-
MBJ
27h 40m2 stops
$669Multiple Airlines
Sat, Jun 13 - Sat, Sep 5

American Airlines flights from Montego Bay to Chicago

Our best American Airlines deals on Montego Bay to Chicago flight tickets
American Airlines
Jun 13
MBJ2:23 pmMontego Bay Sangster Intl
4h 37m
ORD7:00 pmChicago O'Hare Intl
Sep 5
ORD6:25 pmChicago O'Hare Intl
15h 00m
1 stop
MBJ9:25 amMontego Bay Sangster Intl
$470
Find similar
American Airlines
Jun 13
MBJ3:05 pmMontego Bay Sangster Intl
7h 44m
1 stop
ORD10:49 pmChicago O'Hare Intl
Sep 5
ORD8:34 pmChicago O'Hare Intl
12h 51m
1 stop
MBJ9:25 amMontego Bay Sangster Intl
$480
Find similar
American Airlines
Jun 13
MBJ2:23 pmMontego Bay Sangster Intl
4h 37m
ORD7:00 pmChicago O'Hare Intl
Sep 5
ORD8:30 amChicago O'Hare Intl
4h 01m
MBJ12:31 pmMontego Bay Sangster Intl
$578
Find similar

Air Canada flights from Montego Bay to Chicago

Our best Air Canada deals on Montego Bay to Chicago flight tickets
Air Canada
Jan 7
MBJ1:30 pmMontego Bay Sangster Intl
24h 31m
1 stop
ORD1:01 pmChicago O'Hare Intl
Jan 14
ORD10:00 amChicago O'Hare Intl
25h 30m
1 stop
MBJ12:30 pmMontego Bay Sangster Intl
$541
Find similar
Air Canada
Jan 7
MBJ1:30 pmMontego Bay Sangster Intl
31h 40m
2 stops
ORD8:10 pmChicago O'Hare Intl
Jan 14
ORD6:00 pmChicago O'Hare Intl
17h 30m
2 stops
MBJ12:30 pmMontego Bay Sangster Intl
$554
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montego Bay to Chicago 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 December 27, 2025.
Use the filters below to find and compare flights from Montego Bay to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 6/13

2:23 pm-7:00 pm

Nonstop4h 37m

Chicago O'Hare Intl

Sat 9/5

6:25 pm-9:25 am

1 stop15h 00m

$470

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 6/13

3:05 pm-10:49 pm

1 stop7h 44m

Chicago O'Hare Intl

Sat 9/5

8:34 pm-9:25 am

1 stop12h 51m

$480

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 6/13

12:15 pm-1:25 pm

1 stop25h 10m

Chicago O'Hare Intl

Sat 9/5

9:30 am-9:39 am

2 stops24h 09m

$519

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 1/7

1:30 pm-1:01 pm

1 stop24h 31m

Chicago O'Hare Intl

Wed 1/14

10:00 am-12:30 pm

1 stop25h 30m

$541

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 1/7

1:30 pm-8:10 pm

2 stops31h 40m

Chicago O'Hare Intl

Wed 1/14

6:00 pm-12:30 pm

2 stops17h 30m

$554

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 6/13

2:23 pm-7:00 pm

Nonstop4h 37m

Chicago O'Hare Intl

Sat 9/5

8:30 am-12:31 pm

Nonstop4h 01m

$578

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 6/13

12:15 pm-8:08 pm

2 stops31h 53m

Chicago O'Hare Intl

Sat 9/5

9:30 am-1:10 pm

2 stops27h 40m

$669

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 2/4

12:57 pm-11:47 pm

1 stop11h 50m

$155

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 2/7

12:57 pm-9:03 pm

1 stop9h 06m

$162

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 2/5

12:57 pm-9:03 pm

1 stop9h 06m

$165

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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

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?

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

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $436. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Montego Bay to Chicago for around $557.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Montego Bay to Chicago during this time can be as low as $454. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $502.

What is the cheapest Montego Bay Sangster Intl to Chicago flight route?

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

What cabin class options are available on Montego Bay Sangster Intl to Chicago flights?

There are 3 cabin classes available to choose from on Montego Bay Sangster Intl to Chicago 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 flights?

You could potentially save up to 10% on your flight if you consider stops on a Montego Bay to Chicago flight.

How have Montego Bay to Chicago flight prices changed over time?

As of December 2025, prices for Montego Bay to Chicago flights are approximately 17% cheaper when compared to flights at the same time last year.

When to book flights from Montego Bay to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Montego Bay to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montego Bay to Chicago (MBJ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montego Bay to Chicago

Best Price Found

$235

Fastest flight time

12h 21m

Direct flights

Mon, Tue, Wed, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Montego Bay in the past 72 hours is $235. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $433.
The fastest flight from Montego Bay to Chicago takes 12h 21m
Direct flights go from Montego Bay to Chicago on Monday, Tuesday, Wednesday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Montego Bay there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

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

    The distance between Montego Bay Sangster Intl and Chicago is about 1713.9 mi. 12h 21m is a normal flight duration for this route.

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

    Prices for flights from Montego Bay Sangster Intl Airport to Chicago are refreshed on a daily basis.

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

  • How old do you have to be to fly from Montego Bay Sangster Intl Airport to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago 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. 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?

  • What is the most popular airline from Montego Bay to Chicago?

Best airlines flying from Montego Bay to Chicago

Compare and see reviews for airlines that fly from Montego Bay to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $256Free CancellationRating
6.3
8,210 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,066 reviews
Search American Airlines flights
United AirlinesPriceFrom $349Free CancellationRating
7.4
9,115 reviews
Search United Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,256 reviews
Search Southwest flights

  • Southwest Flights From Montego Bay to Chicago

    Across 1 Southwest flight from Montego Bay to Chicago this week, the average price was $536, with the best Southwest deals starting from $392 round-trip. 4,256 users have rated Southwest on momondo, with an average score of 8.0/10.

  • American Airlines Flights From Montego Bay to Chicago

    Across 11,066 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Montego Bay to Chicago about 7 times each week, with ticket deals ranging from $348 to $481. Price data is based on momondo searches in the last 72 hours.

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
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?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Montego Bay to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from Montego Bay with this policy.

How can momondo help me find flights from Montego Bay to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Montego Bay to Chicago.

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 not ready to book a flight from Montego Bay to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport