Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 2/14. 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
1:00 pm - 9:13 pm
MBJ
-
ORD
9h 13m
1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
$230Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
Spirit Airlines Logo
12:00 pm - 7:46 pm
MBJ
-
ORD
7h 46m
1 stop
Spirit Airlines Logo
8:41 pm - 11:02 am
ORD
-
MBJ
14h 21m
1 stop
$269Spirit Airlines
Tue, Mar 24 - Tue, Apr 14
American Airlines Logo
1:14 pm - 5:55 pm
MBJ
-
ORD
4h 41mnonstop
American Airlines Logo
8:10 am - 12:15 pm
ORD
-
MBJ
4h 05mnonstop
$320American Airlines
Tue, Mar 24 - Tue, Apr 14
United Airlines Logo
1:48 pm - 6:13 pm
MBJ
-
ORD
4h 25mnonstop
United Airlines Logo
8:45 am - 3:10 pm
ORD
-
MBJ
6h 25m
1 stop
$325United Airlines
Tue, Mar 24 - Tue, Apr 14
Spirit Airlines Logo
1:00 pm - 7:54 am
MBJ
-
ORD
19h 54m
2 stops
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
$329Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
3:20 pm - 11:53 pm
MBJ
-
ORD
8h 33m
1 stop
American Airlines Logo
6:58 pm - 11:51 am
ORD
-
MBJ
16h 53m
1 stop
$335American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
1:15 pm - 5:58 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
8:10 am - 12:15 pm
ORD
-
MBJ
4h 05mnonstop
$345American Airlines
Mon, Apr 13 - Tue, Apr 21
American Airlines Logo
1:15 pm - 5:58 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
5:00 am - 11:24 am
ORD
-
MBJ
6h 24m
1 stop
$350American Airlines
Mon, Apr 13 - Tue, Apr 21
Delta Logo
11:15 am - 11:54 pm
MBJ
-
ORD
12h 39m
1 stop
Delta Logo
7:00 am - 3:17 pm
ORD
-
MBJ
8h 17m
2 stops
$351Delta
Tue, Mar 24 - Tue, Apr 14
Spirit Airlines Logo
1:00 pm - 9:22 am
MBJ
-
ORD
21h 22m
3 stops
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
$360Spirit Airlines
Wed, Feb 25 - Wed, Mar 4

Air Canada flights from Montego Bay to Chicago O'Hare Intl Airport

Our best Air Canada deals on Montego Bay to Chicago O'Hare Intl Airport flight tickets
Air Canada
Apr 13
MBJ12:40 pmMontego Bay Sangster Intl
23h 37m
2 stops
ORD12:17 pmChicago O'Hare Intl
Apr 21
ORD8:20 pmChicago O'Hare Intl
15h 15m
1 stop
MBJ11:35 amMontego Bay Sangster Intl
$409
Air Canada
Mar 30
MBJ12:40 pmMontego Bay Sangster Intl
21h 10m
1 stop
ORD9:50 amChicago O'Hare Intl
Apr 6
ORD6:21 pmChicago O'Hare Intl
41h 14m
2 stops
MBJ11:35 amMontego Bay Sangster Intl
$447
Air Canada
Mar 30
MBJ12:40 pmMontego Bay Sangster Intl
22h 13m
2 stops
ORD10:53 amChicago O'Hare Intl
Apr 6
ORD6:21 pmChicago O'Hare Intl
41h 14m
2 stops
MBJ11:35 amMontego Bay Sangster Intl
$450

American Airlines flights from Montego Bay to Chicago O'Hare Intl Airport

Our best American Airlines deals on Montego Bay to Chicago O'Hare Intl Airport flight tickets
American Airlines
Mar 24
MBJ1:14 pmMontego Bay Sangster Intl
4h 41m
ORD5:55 pmChicago O'Hare Intl
Apr 14
ORD8:10 amChicago O'Hare Intl
4h 05m
MBJ12:15 pmMontego Bay Sangster Intl
$320
American Airlines
May 14
MBJ3:20 pmMontego Bay Sangster Intl
8h 33m
1 stop
ORD11:53 pmChicago O'Hare Intl
May 18
ORD6:58 pmChicago O'Hare Intl
16h 53m
1 stop
MBJ11:51 amMontego Bay Sangster Intl
$335
American Airlines
Apr 13
MBJ1:15 pmMontego Bay Sangster Intl
4h 43m
ORD5:58 pmChicago O'Hare Intl
Apr 21
ORD8:10 amChicago O'Hare Intl
4h 05m
MBJ12:15 pmMontego Bay Sangster Intl
$345

momondo Fare Finder

 
Customize your flight search to find flights from Montego Bay to Chicago O'Hare Intl Airport 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 January 29, 2026.
Use the filters below to find and compare flights from Montego Bay to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-9:13 pm

1 stop9h 13m

Chicago O'Hare Intl

Wed 3/4

5:15 am-12:02 pm

1 stop5h 47m

$230

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

12:00 pm-7:46 pm

1 stop7h 46m

Chicago O'Hare Intl

Tue 4/14

8:41 pm-11:02 am

1 stop14h 21m

$269

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

1:14 pm-5:55 pm

Nonstop4h 41m

Chicago O'Hare Intl

Tue 4/14

8:10 am-12:15 pm

Nonstop4h 05m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Tue 4/14

8:45 am-3:10 pm

1 stop6h 25m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-7:54 am

2 stops19h 54m

Chicago O'Hare Intl

Wed 3/4

5:15 am-12:02 pm

1 stop5h 47m

$329

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 5/14

3:20 pm-11:53 pm

1 stop8h 33m

Chicago O'Hare Intl

Mon 5/18

6:58 pm-11:51 am

1 stop16h 53m

$335

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 4/13

1:15 pm-5:58 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 4/21

8:10 am-12:15 pm

Nonstop4h 05m

$345

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Mon 4/13

1:15 pm-5:58 pm

Nonstop4h 43m

Chicago O'Hare Intl

Tue 4/21

5:00 am-11:24 am

1 stop6h 24m

$350

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/24

11:15 am-11:54 pm

1 stop12h 39m

Chicago O'Hare Intl

Tue 4/14

7:00 am-3:17 pm

2 stops8h 17m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 2/25

1:00 pm-9:22 am

3 stops21h 22m

Chicago O'Hare Intl

Wed 3/4

5:15 am-12:02 pm

1 stop5h 47m

$360

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $438. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Montego Bay because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $557.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Montego Bay at noon is the least expensive time of day to depart. momondo users have found prices as low as $494 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $507. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

You could potentially save up to 25% on your flight if you consider stops on a Montego Bay to Chicago O'Hare Intl Airport flight.

How have Montego Bay to Chicago O'Hare Intl Airport flight prices changed over time?

As of January 2026, prices for Montego Bay to Chicago O'Hare Intl Airport flights are approximately 24% more expensive when compared to flights at the same time last year.

When to book flights from Montego Bay to Chicago O'Hare Intl Airport

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

Cheap Montego Bay to Chicago O'Hare Intl Airport (MBJ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montego Bay to Chicago O'Hare Intl Airport

Best Price Found

$282

Fastest flight time

4h 23m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Montego Bay in the past 72 hours is $282. The best round-trip flight deal from Montego Bay to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $365.
The fastest flight from Montego Bay to Chicago O'Hare Intl Airport takes 4h 23m
Direct flights go from Montego Bay to Chicago O'Hare Intl Airport every day.
Search flight deals

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

    The distance between Montego Bay Sangster Intl and Chicago O'Hare Intl is about 1726.0 mi. A reasonable flight in good conditions will take 4h 23m.

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

    Prices for flights from Montego Bay Sangster Intl Airport to Chicago O'Hare Intl Airport refresh daily.

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

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

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Montego Bay to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Montego Bay to Chicago O'Hare Intl Airport?

Best airlines flying from Montego Bay to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Montego Bay to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $256Free CancellationRating
6.3
8,394 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,206 reviews
Search American Airlines flights
United AirlinesPriceFrom $349Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights

  • American Airlines Flights From Montego Bay to Chicago O'Hare Intl Airport

    American Airlines flight deals from Montego Bay to Chicago O'Hare Intl Airport start from $348 round-trip. Over the 5 American Airlines flights for this route in a normal week, average airfare is usually $472 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Montego Bay to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Montego Bay.

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

Flights from Montego Bay to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Montego Bay to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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 simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Montego Bay and alert you when they change.

An easier way to manage your Chicago O'Hare Intl Airport 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 2/28
Sat 3/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago