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Cheap flights from Montego Bay to Chicago from $219

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 8/22. 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.
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
9:00 am - 1:12 pm
ORD
-
MBJ
4h 12mnonstop
$351American Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
6:45 am - 2:23 pm
ORD
-
MBJ
7h 38m
1 stop
$356American Airlines
Tue, Sep 1 - Tue, Sep 8
Delta Logo
2:26 pm - 11:59 pm
MBJ
-
ORD
9h 33m
1 stop
Delta Logo
6:45 am - 1:20 pm
ORD
-
MBJ
6h 35m
1 stop
$357Delta
Fri, Oct 2 - Tue, Oct 6
Delta Logo
2:26 pm - 10:45 pm
MBJ
-
MDW
8h 19m
1 stop
Delta Logo
6:00 am - 1:20 pm
MDW
-
MBJ
7h 20m
1 stop
$357Delta
Fri, Oct 2 - Tue, Oct 6
United Airlines Logo
3:45 pm - 7:50 am
MBJ
-
ORD
17h 05m
1 stop
United Airlines Logo
8:40 am - 1:48 pm
ORD
-
MBJ
4h 08mnonstop
$362United Airlines
Sun, Nov 1 - Mon, Nov 30
United Airlines Logo
3:45 pm - 9:00 am
MBJ
-
ORD
18h 15m
1 stop
United Airlines Logo
8:17 pm - 2:39 pm
ORD
-
MBJ
17h 22m
1 stop
$363United Airlines
Sat, Dec 19 - Sat, Jan 2
Southwest Logo
12:00 pm - 11:10 pm
MBJ
-
MDW
11h 10m
2 stops
Southwest Logo
5:45 am - 11:50 am
MDW
-
MBJ
6h 05m
1 stop
$454Southwest
Fri, Oct 2 - Tue, Oct 6
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
11:45 am - 12:17 pm
MDW
-
MBJ
24h 32m
1 stop
$475Frontier
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
12:00 pm - 11:55 pm
MBJ
-
MDW
11h 55m
2 stops
Southwest Logo
8:55 pm - 11:50 am
MDW
-
MBJ
14h 55m
2 stops
$487Southwest
Fri, Oct 2 - Mon, Oct 5
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
Frontier Logo
6:05 am - 12:24 pm
MDW
-
MBJ
6h 19m
1 stop
$492Frontier
Thu, Aug 13 - Sun, Aug 16

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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
Sep 1
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
$351
American Airlines
Sep 1
MBJ2:12 pmMontego Bay Sangster Intl
4h 43m
ORD6:55 pmChicago O'Hare Intl
Sep 8
ORD6:45 amChicago O'Hare Intl
7h 38m
1 stop
MBJ2:23 pmMontego Bay Sangster Intl
$356
American Airlines
Aug 22
MBJ5:08 pmMontego Bay Sangster Intl
14h 26m
1 stop
ORD7:34 amChicago O'Hare Intl
Aug 24
ORD9:00 amChicago O'Hare Intl
4h 12m
MBJ1:12 pmMontego Bay Sangster Intl
$360

United Airlines flights from Montego Bay to Chicago

Our best United Airlines deals on Montego Bay to Chicago flight tickets
United Airlines
Jul 25
MBJ4:33 pmMontego Bay Sangster Intl
8h 12m
1 stop
ORD12:45 amChicago O'Hare Intl
Jul 27
ORD6:29 amChicago O'Hare Intl
7h 01m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
$390
United Airlines
Aug 1
MBJ4:33 pmMontego Bay Sangster Intl
8h 12m
1 stop
ORD12:45 amChicago O'Hare Intl
Aug 15
ORD11:15 amChicago O'Hare Intl
27h 55m
1 stop
MBJ3:10 pmMontego Bay Sangster Intl
$507
United Airlines
Jul 24
MBJ2:40 pmMontego Bay Sangster Intl
19h 40m
1 stop
ORD10:20 amChicago O'Hare Intl
Aug 1
ORD6:40 pmChicago O'Hare Intl
20h 46m
1 stop
MBJ3:26 pmMontego Bay Sangster Intl
$547

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 July 21, 2026.
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

Cheapest round-trip
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 9/1

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 9/8

9:00 am-1:12 pm

Nonstop4h 12m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 9/1

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 9/8

6:45 am-2:23 pm

1 stop7h 38m

$356

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 10/2

2:26 pm-11:59 pm

1 stop9h 33m

Chicago O'Hare Intl

Tue 10/6

6:45 am-1:20 pm

1 stop6h 35m

$357

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 10/2

2:26 pm-10:45 pm

1 stop8h 19m

Chicago Midway

Tue 10/6

6:00 am-1:20 pm

1 stop7h 20m

$357

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 11/1

3:45 pm-7:50 am

1 stop17h 05m

Chicago O'Hare Intl

Mon 11/30

8:40 am-1:48 pm

Nonstop4h 08m

$362

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 12/19

3:45 pm-9:00 am

1 stop18h 15m

Chicago O'Hare Intl

Sat 1/2

8:17 pm-2:39 pm

1 stop17h 22m

$363

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 10/2

12:00 pm-11:10 pm

2 stops11h 10m

Chicago Midway

Tue 10/6

5:45 am-11:50 am

1 stop6h 05m

$454

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 8/15

1:32 pm-10:03 pm

1 stop8h 31m

Chicago Midway

Sat 8/22

11:45 am-12:17 pm

1 stop24h 32m

$475

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Fri 10/2

12:00 pm-11:55 pm

2 stops11h 55m

Chicago Midway

Mon 10/5

8:55 pm-11:50 am

2 stops14h 55m

$487

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 8/13

1:32 pm-10:03 pm

1 stop8h 31m

Chicago Midway

Sun 8/16

6:05 am-12:24 pm

1 stop6h 19m

$492

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 $354. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Montego Bay to Chicago during May average around $371.

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 $413. 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 $531.

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 $467.

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?

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 July 2026, prices for Montego Bay to Chicago flights are approximately 24% 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

$215

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 $215. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $385.
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
10,011 reviews
Search United Airlines flights
American AirlinesPriceFrom $281Free CancellationRating
7.1
11,832 reviews
Search American 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 $411, with the best American Airlines deals starting from $281 round-trip. 11,832 users have rated American Airlines on momondo, with an average score of 7.1/10.

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
Lansing
Saint Joseph
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

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