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Cheap flights from Montego Bay to Chicago from $149

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 9/17. 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 (MBJ-CHI)

Cheap round-trip flights

Spirit Airlines Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Spirit Airlines Logo
5:05 am - 11:05 amORD-MBJ
6h 00m1 stop
$263Spirit Airlines
Find Deal
Sat, Sep 13 - Sat, Oct 4
Spirit Airlines Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Spirit Airlines Logo
6:44 pm - 11:05 amORD-MBJ
16h 21m1 stop
$267Spirit Airlines
Find Deal
Wed, Sep 24 - Mon, Sep 29
American Airlines Logo
1:50 pm - 6:23 pmMBJ-ORD
4h 33mnonstop
American Airlines Logo
7:10 am - 3:05 pmORD-MBJ
7h 55m1 stop
$338American Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
Delta Logo
2:35 pm - 9:36 pmMBJ-MDW
7h 01m1 stop
Delta Logo
6:00 am - 12:07 pmMDW-MBJ
6h 07m1 stop
$339Delta
Find Deal
Fri, Oct 3 - Tue, Oct 7
Delta Logo
12:50 pm - 8:40 amMBJ-ORD
19h 50m2 stops
Delta Logo
7:59 pm - 12:07 pmORD-MBJ
16h 08m1 stop
$345Delta
Find Deal
Wed, Oct 1 - Mon, Oct 6
Logo
12:10 pm - 10:52 amMBJ-ORD
22h 42m1 stop
Logo
8:49 pm - 11:05 amORD-MBJ
14h 16m2 stops
$350
Find Deal
Fri, Sep 19 - Mon, Sep 22
American Airlines Logo
2:38 pm - 11:48 pmMBJ-ORD
9h 10m2 stops
American Airlines Logo
6:00 am - 2:54 pmORD-MBJ
8h 54m2 stops
$353American Airlines
Find Deal
Wed, Sep 24 - Tue, Sep 30
United Airlines Logo
3:36 pm - 11:34 pmMBJ-ORD
8h 58m1 stop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$384United Airlines
Find Deal
Thu, Nov 20 - Thu, Nov 27
Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Logo
4:51 pm - 1:20 pmORD-MBJ
20h 29m1 stop
$396
Find Deal
Wed, Oct 1 - Thu, Oct 9
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$465United Airlines
Find Deal
Sun, Dec 21 - Wed, Dec 31

American Airlines flights from Montego Bay to Chicago

Our best American Airlines deals on Montego Bay to Chicago flight tickets
American Airlines
Oct 8
MBJ1:50 pmMontego Bay Sangster Intl
4h 33m
ORD6:23 pmChicago O'Hare Intl
Oct 15
ORD7:10 amChicago O'Hare Intl
7h 55m
1 stop
MBJ3:05 pmMontego Bay Sangster Intl
$338
Find similar
American Airlines
Sep 24
MBJ2:38 pmMontego Bay Sangster Intl
9h 10m
2 stops
ORD11:48 pmChicago O'Hare Intl
Sep 30
ORD6:00 amChicago O'Hare Intl
8h 54m
2 stops
MBJ2:54 pmMontego Bay Sangster Intl
$353
Find similar
American Airlines
Oct 1
MBJ1:55 pmMontego Bay Sangster Intl
9h 53m
2 stops
ORD11:48 pmChicago O'Hare Intl
Oct 5
ORD5:30 pmChicago O'Hare Intl
20h 00m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$404
Find similar

United Airlines flights from Montego Bay to Chicago

Our best United Airlines deals on Montego Bay to Chicago flight tickets
United Airlines
Nov 20
MBJ3:36 pmMontego Bay Sangster Intl
8h 58m
1 stop
ORD11:34 pmChicago O'Hare Intl
Nov 27
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
$384
Find similar
United Airlines
Dec 21
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
Dec 31
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
$465
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 August 26, 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 9/13

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Sat 10/4

5:05 am-11:05 am

1 stop6h 00m

$263

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/24

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Mon 9/29

6:44 pm-11:05 am

1 stop16h 21m

$267

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 10/8

1:50 pm-6:23 pm

Nonstop4h 33m

Chicago O'Hare Intl

Wed 10/15

7:10 am-3:05 pm

1 stop7h 55m

$338

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 10/3

2:35 pm-9:36 pm

1 stop7h 01m

Chicago Midway

Tue 10/7

6:00 am-12:07 pm

1 stop6h 07m

$339

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 10/1

12:50 pm-8:40 am

2 stops19h 50m

Chicago O'Hare Intl

Mon 10/6

7:59 pm-12:07 pm

1 stop16h 08m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 9/19

12:10 pm-10:52 am

1 stop22h 42m

Chicago O'Hare Intl

Mon 9/22

8:49 pm-11:05 am

2 stops14h 16m

$350

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 9/24

2:38 pm-11:48 pm

2 stops9h 10m

Chicago O'Hare Intl

Tue 9/30

6:00 am-2:54 pm

2 stops8h 54m

$353

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/20

3:36 pm-11:34 pm

1 stop8h 58m

Chicago O'Hare Intl

Thu 11/27

8:42 am-1:46 pm

Nonstop4h 04m

$384

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 10/1

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

Thu 10/9

4:51 pm-1:20 pm

1 stop20h 29m

$396

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 12/21

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Wed 12/31

8:42 am-1:46 pm

Nonstop4h 04m

$465

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

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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Montego Bay, with most prices found around $351. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Montego Bay to Chicago during August average around $400.

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 $447. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Montego Bay to Chicago for around $543.

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 $448. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $505.

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?

No. A direct flight is the cheapest option for a flight between Montego Bay to Chicago.

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

As of August 2025, prices for Montego Bay to Chicago flights are approximately 55% more expensive 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

$292

Fastest flight time

4h 10m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Montego Bay in the past 72 hours is $292. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $437.
The fastest flight from Montego Bay to Chicago takes 4h 10m
Direct flights go from Montego Bay to Chicago every day.
There are 2 airports near Chicago: 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. 4h 10m 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 $251Free CancellationRating
6.3
8,031 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $370Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $409Free CancellationRating
7.4
8,943 reviews
Search United Airlines flights

  • American Airlines Flights From Montego Bay to Chicago

    Across 7 American Airlines flights from Montego Bay to Chicago this week, the average price was $488, with the best American Airlines deals starting from $370 round-trip. 10,000 users have rated American Airlines on momondo, with an average score of 7.2/10.

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
Lansing
Portage
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?

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