Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Montego Bay to Chicago from $151

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 12/9. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Montego Bay to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
1:07 pm - 11:29 pmMBJ-ORD
11h 22m1 stop
Spirit Airlines Logo
5:00 am - 12:05 pmORD-MBJ
6h 05m1 stop
$301Spirit Airlines
Find Deal
Sat, Nov 22 - Sun, Jan 4
American Airlines Logo
2:30 pm - 6:17 pmMBJ-ORD
4h 47mnonstop
American Airlines Logo
9:58 am - 3:11 pmORD-MBJ
4h 13mnonstop
$328American Airlines
Find Deal
Fri, Dec 12 - Fri, Jan 2
American Airlines Logo
3:12 pm - 6:59 pmMBJ-ORD
4h 47mnonstop
American Airlines Logo
7:11 am - 4:22 pmORD-MBJ
8h 11m1 stop
$333American Airlines
Find Deal
Fri, Dec 12 - Fri, Jan 2
Delta Logo
1:55 pm - 9:39 pmMBJ-ORD
8h 44m1 stop
Delta Logo
7:00 am - 8:41 pmORD-MBJ
12h 41m2 stops
$334Delta
Find Deal
Fri, Dec 12 - Fri, Jan 2
Frontier Logo
4:50 pm - 7:20 amMBJ-ORD
15h 30m2 stops
Frontier Logo
6:00 am - 2:54 pmORD-MBJ
7h 54m1 stop
$350Frontier
Find Deal
Sat, Nov 22 - Sun, Jan 4
Frontier Logo
11:12 am - 10:46 pmMBJ-ORD
12h 34m1 stop
Frontier Logo
12:44 pm - 8:59 amORD-MBJ
19h 15m1 stop
$367Frontier
Find Deal
Sat, Dec 27 - Sun, Dec 28
American Airlines Logo
3:13 pm - 6:54 pmMBJ-ORD
4h 41mnonstop
American Airlines Logo
7:17 pm - 10:17 amORD-MBJ
14h 00m1 stop
$373American Airlines
Find Deal
Mon, Nov 24 - Sun, Nov 30
Frontier Logo
3:34 pm - 10:12 pmMBJ-MDW
7h 38m1 stop
Frontier Logo
6:00 am - 8:59 amMDW-MBJ
25h 59m1 stop
$374Frontier
Find Deal
Sat, Dec 27 - Sun, Dec 28
Southwest Logo
3:55 pm - 11:00 pmMBJ-MDW
8h 05m1 stop
Southwest Logo
5:25 am - 2:55 pmMDW-MBJ
8h 30m1 stop
$469Southwest
Find Deal
Mon, Nov 24 - Sun, Nov 30
Southwest Logo
3:55 pm - 11:05 pmMBJ-MDW
8h 10m1 stop
Southwest Logo
5:45 am - 2:25 pmMDW-MBJ
7h 40m1 stop
$528Southwest
Find Deal
Sun, Dec 28 - Tue, Dec 30

United Airlines flights from Montego Bay to Chicago

Our best United Airlines deals on Montego Bay to Chicago flight tickets
United Airlines
Dec 3
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
Dec 5
ORD9:08 pmChicago O'Hare Intl
15h 57m
1 stop
MBJ2:05 pmMontego Bay Sangster Intl
$331
Find similar
United Airlines
Dec 28
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
Jan 4
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
$384
Find similar
United Airlines
Dec 28
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
Jan 4
ORD9:23 pmChicago O'Hare Intl
15h 42m
1 stop
MBJ2:05 pmMontego Bay Sangster Intl
$388
Find similar

Delta flights from Montego Bay to Chicago

Our best Delta deals on Montego Bay to Chicago flight tickets
Delta
Dec 12
MBJ1:55 pmMontego Bay Sangster Intl
8h 44m
1 stop
ORD9:39 pmChicago O'Hare Intl
Jan 2
ORD7:00 amChicago O'Hare Intl
12h 41m
2 stops
MBJ8:41 pmMontego Bay Sangster Intl
$334
Find similar
Delta
Dec 3
MBJ2:29 pmMontego Bay Sangster Intl
9h 14m
1 stop
ORD10:43 pmChicago O'Hare Intl
Dec 5
ORD6:45 amChicago O'Hare Intl
8h 48m
2 stops
MBJ4:33 pmMontego Bay Sangster Intl
$367
Find similar
Delta
Dec 22
MBJ8:00 amMontego Bay Sangster Intl
8h 13m
1 stop
ORD3:13 pmChicago O'Hare Intl
Jan 10
ORD6:50 amChicago O'Hare Intl
12h 46m
2 stops
MBJ8:36 pmMontego Bay Sangster Intl
$415
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 November 13, 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 11/22

1:07 pm-11:29 pm

1 stop11h 22m

Chicago O'Hare Intl

Sun 1/4

5:00 am-12:05 pm

1 stop6h 05m

$301

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

2:30 pm-6:17 pm

Nonstop4h 47m

Chicago O'Hare Intl

Fri 1/2

9:58 am-3:11 pm

Nonstop4h 13m

$328

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

3:12 pm-6:59 pm

Nonstop4h 47m

Chicago O'Hare Intl

Fri 1/2

7:11 am-4:22 pm

1 stop8h 11m

$333

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 12/12

1:55 pm-9:39 pm

1 stop8h 44m

Chicago O'Hare Intl

Fri 1/2

7:00 am-8:41 pm

2 stops12h 41m

$334

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 11/22

4:50 pm-7:20 am

2 stops15h 30m

Chicago O'Hare Intl

Sun 1/4

6:00 am-2:54 pm

1 stop7h 54m

$350

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 12/27

11:12 am-10:46 pm

1 stop12h 34m

Chicago O'Hare Intl

Sun 12/28

12:44 pm-8:59 am

1 stop19h 15m

$367

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 11/24

3:13 pm-6:54 pm

Nonstop4h 41m

Chicago O'Hare Intl

Sun 11/30

7:17 pm-10:17 am

1 stop14h 00m

$373

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sat 12/27

3:34 pm-10:12 pm

1 stop7h 38m

Chicago Midway

Sun 12/28

6:00 am-8:59 am

1 stop25h 59m

$374

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Mon 11/24

3:55 pm-11:00 pm

1 stop8h 05m

Chicago Midway

Sun 11/30

5:25 am-2:55 pm

1 stop8h 30m

$469

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 12/28

3:55 pm-11:05 pm

1 stop8h 10m

Chicago Midway

Tue 12/30

5:45 am-2:25 pm

1 stop7h 40m

$528

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 $440. 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 $633.

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 $501.

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.

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

As of November 2025, prices for Montego Bay to Chicago flights are approximately 1% 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

$234

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 $234. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $344.
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
8,139 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,049 reviews
Search American Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
United AirlinesPriceFrom $409Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights

  • United Airlines Flights From Montego Bay to Chicago

    Across 2 United Airlines flights from Montego Bay to Chicago this week, the average price was $484, with the best United Airlines deals starting from $409 round-trip. 9,015 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Montego Bay to Chicago

    Across 11,049 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
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 12/13
Sat 12/20
By creating a price alert you accept our terms of use and privacy policy.

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