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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.
Frontier Logo
4:23 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 24m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:16 am - 3:29 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 13m1 stop Atlanta Hartsfield-Jackson
$368Frontier
Mon, Nov 2 - Thu, Nov 12
Frontier Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:16 am - 3:08 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
7h 52m1 stop Atlanta Hartsfield-Jackson
$371Frontier
Mon, Oct 26 - Mon, Nov 2
Frontier Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 18m1 stop Atlanta Hartsfield-Jackson
$381Frontier
Thu, Oct 22 - Mon, Oct 26
Frontier Logo
4:23 pm - 11:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 24m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:42 pm - 3:29 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 47m1 stop Atlanta Hartsfield-Jackson
$384Frontier
Mon, Nov 2 - Wed, Nov 11
American Airlines Logo
6:09 pm - 9:30 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
16h 21m1 stop Miami
American Airlines Logo
8:50 pm - 12:45 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
14h 55m1 stop Philadelphia
$386American Airlines
Tue, Nov 24 - Sat, Nov 28
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
$401American Airlines
Tue, Nov 3 - Fri, Nov 13
American Airlines Logo
3:56 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 50mnonstop
American Airlines Logo
7:50 pm - 12:21 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
15h 31m1 stop Miami
$406American Airlines
Tue, Nov 3 - Fri, Nov 13
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
$411United Airlines
Tue, Nov 3 - Tue, Nov 10
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
$411United Airlines
Fri, Nov 6 - Sun, Nov 8
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
$411United Airlines
Thu, Nov 5 - Mon, Nov 9

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American Airlines flights from Montego Bay to Chicago

Our best American Airlines deals on Montego Bay to Chicago flight tickets
American Airlines
Nov 24
MBJ6:09 pmMontego Bay Sangster Intl
16h 21m
1 stop
ORD9:30 amChicago O'Hare Intl
Nov 28
ORD8:50 pmChicago O'Hare Intl
14h 55m
1 stop
MBJ12:45 pmMontego Bay Sangster Intl
$386
American Airlines
Nov 3
MBJ3:56 pmMontego Bay Sangster Intl
4h 50m
ORD7:46 pmChicago O'Hare Intl
Nov 13
ORD9:40 amChicago O'Hare Intl
4h 12m
MBJ2:52 pmMontego Bay Sangster Intl
$401
American Airlines
Nov 3
MBJ3:56 pmMontego Bay Sangster Intl
4h 50m
ORD7:46 pmChicago O'Hare Intl
Nov 13
ORD7:50 pmChicago O'Hare Intl
15h 31m
1 stop
MBJ12:21 pmMontego Bay Sangster Intl
$406

United Airlines flights from Montego Bay to Chicago

Our best United Airlines deals on Montego Bay to Chicago flight tickets
United Airlines
Nov 3
MBJ2:54 pmMontego Bay Sangster Intl
4h 26m
ORD6:20 pmChicago O'Hare Intl
Nov 9
ORD8:40 amChicago O'Hare Intl
4h 08m
MBJ1:48 pmMontego Bay Sangster Intl
$411
United Airlines
Nov 23
MBJ2:54 pmMontego Bay Sangster Intl
4h 26m
ORD6:20 pmChicago O'Hare Intl
Nov 29
ORD8:40 amChicago O'Hare Intl
4h 08m
MBJ1:48 pmMontego Bay Sangster Intl
$421
United Airlines
Dec 29
MBJ2:54 pmMontego Bay Sangster Intl
4h 26m
ORD6:20 pmChicago O'Hare Intl
Jan 4
ORD8:40 amChicago O'Hare Intl
4h 08m
MBJ1:48 pmMontego Bay Sangster Intl
$424

momondo Fare Finder

 
Use the filters below to find and compare flights from Montego Bay to Chicago that are best for you.

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Route

Depart

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Price

Cheapest round-trip

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Mon 11/2

4:23 pm-11:47 pm

1 stop8h 24m

Chicago Midway

Thu 11/12

6:16 am-3:29 pm

1 stop8h 13m

$368

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Mon 10/26

3:48 pm-11:43 pm

1 stop7h 55m

Chicago Midway

Mon 11/2

6:16 am-3:08 pm

1 stop7h 52m

$371

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Thu 10/22

3:48 pm-11:43 pm

1 stop7h 55m

Chicago Midway

Mon 10/26

6:15 am-2:33 pm

1 stop8h 18m

$381

Montego BayChicago

MBJ Montego Bay Sangster Intl - MDW Chicago Midway

MBJMDW

Montego Bay Sangster Intl

Mon 11/2

4:23 pm-11:47 pm

1 stop8h 24m

Chicago Midway

Wed 11/11

6:42 pm-3:29 pm

1 stop19h 47m

$384

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 11/24

6:09 pm-9:30 am

1 stop16h 21m

Chicago O'Hare Intl

Sat 11/28

8:50 pm-12:45 pm

1 stop14h 55m

$386

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 11/3

3:56 pm-7:46 pm

Nonstop4h 50m

Chicago O'Hare Intl

Fri 11/13

9:40 am-2:52 pm

Nonstop4h 12m

$401

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 11/3

3:56 pm-7:46 pm

Nonstop4h 50m

Chicago O'Hare Intl

Fri 11/13

7:50 pm-12:21 pm

1 stop15h 31m

$406
Quickest round-trip

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Tue 11/3

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Tue 11/10

8:40 am-1:48 pm

Nonstop4h 08m

$411

Montego BayChicago

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

MBJORD

Montego Bay Sangster Intl

Fri 11/6

2:54 pm-6:20 pm

Nonstop4h 26m

Chicago O'Hare Intl

Sun 11/8

8:40 am-1:48 pm

Nonstop4h 08m

$411

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

$411

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 May is, on average, the cheapest month to fly to Chicago from Montego Bay, with most prices found around $377. If you’re not able to fly to Chicago in May, then April is your next best option. Flight prices from Montego Bay to Chicago during April average around $387.

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 Thursday when prices can be found for as low as $402. 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 $547.

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 at noon. Flights from Montego Bay to Chicago during this time can be as low as $461. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $486.

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 to Chicago flights?

There are 2 cabin classes available to choose from on Montego Bay 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 12% 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 September 2026, prices for Montego Bay to Chicago flights are approximately 14% 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

$209

Fastest flight time

4h 26m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Montego Bay in the past 72 hours is $209. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $368.
The fastest flight from Montego Bay to Chicago takes 4h 26m
Direct flights go from Montego Bay to Chicago every day.
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

Frequently asked questions about flying from Montego Bay to Chicago

  • 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 26m 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
United AirlinesPriceFrom $281Free CancellationRating
7.4
10,255 reviews
Search United Airlines flights
American AirlinesPriceFrom $281Free CancellationRating
7.0
12,095 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport