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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 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.
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0 bags

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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
mié., feb. 25 - mié., 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
mar., mar. 24 - mar., abr. 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
mar., mar. 24 - mar., abr. 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
mar., mar. 24 - mar., abr. 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
mié., feb. 25 - mié., 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
jue., may. 14 - lun., may. 18
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
mar., mar. 24 - mar., abr. 14
Delta Logo
2:40 pm - 9:45 pm
MBJ
-
MDW
7h 05m
1 stop
Delta Logo
6:00 am - 1:16 pm
MDW
-
MBJ
7h 16m
1 stop
$351Delta
jue., may. 14 - lun., may. 18
Southwest Logo
2:20 pm - 6:35 pm
MBJ
-
MDW
4h 15mnonstop
Southwest Logo
8:45 am - 12:35 pm
MDW
-
MBJ
3h 50mnonstop
$531Southwest
sáb., mar. 14 - sáb., mar. 21
Southwest Logo
2:05 pm - 12:50 am
MBJ
-
MDW
10h 45m
2 stops
Southwest Logo
8:45 am - 12:35 pm
MDW
-
MBJ
3h 50mnonstop
$728Southwest
sáb., mar. 14 - sáb., mar. 21

Air Canada flights from Montego Bay to Chicago

Our best Air Canada deals on Montego Bay to Chicago 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

Our best American Airlines deals on Montego Bay to Chicago 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 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 enero 29, 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

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mié. 2/25

1:00 pm-9:13 pm

1 stop9h 13m

Chicago O'Hare Intl

mié. 3/4

5:15 am-12:02 pm

1 stop5h 47m

$230

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 3/24

12:00 pm-7:46 pm

1 stop7h 46m

Chicago O'Hare Intl

mar. 4/14

8:41 pm-11:02 am

1 stop14h 21m

$269

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 3/24

1:14 pm-5:55 pm

Nonstop4h 41m

Chicago O'Hare Intl

mar. 4/14

8:10 am-12:15 pm

Nonstop4h 05m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 3/24

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

mar. 4/14

8:45 am-3:10 pm

1 stop6h 25m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mié. 2/25

1:00 pm-7:54 am

2 stops19h 54m

Chicago O'Hare Intl

mié. 3/4

5:15 am-12:02 pm

1 stop5h 47m

$329

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jue. 5/14

3:20 pm-11:53 pm

1 stop8h 33m

Chicago O'Hare Intl

lun. 5/18

6:58 pm-11:51 am

1 stop16h 53m

$335

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 3/24

11:15 am-11:54 pm

1 stop12h 39m

Chicago O'Hare Intl

mar. 4/14

7:00 am-3:17 pm

2 stops8h 17m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

jue. 5/14

2:40 pm-9:45 pm

1 stop7h 05m

Chicago Midway

lun. 5/18

6:00 am-1:16 pm

1 stop7h 16m

$351

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 3/14

2:20 pm-6:35 pm

Nonstop4h 15m

Chicago Midway

sáb. 3/21

8:45 am-12:35 pm

Nonstop3h 50m

$531

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 3/14

2:05 pm-12:50 am

2 stops10h 45m

Chicago Midway

sáb. 3/21

8:45 am-12:35 pm

Nonstop3h 50m

$728

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 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 $439. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Montego Bay to Chicago for around $557.

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 $498. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $507.

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?

You could potentially save up to 25% 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 January 2026, prices for Montego Bay to Chicago flights are approximately 9% 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

$282

Fastest flight time

4h 15m

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 $282. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $365.
The fastest flight from Montego Bay to Chicago takes 4h 15m
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

  • 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 15m 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 $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
SouthwestPriceFrom $392Free CancellationRating
8.0
4,267 reviews
Search Southwest flights

  • American Airlines Flights From Montego Bay to Chicago

    Across 5 American Airlines flights from Montego Bay to Chicago this week, the average price was $472, with the best American Airlines deals starting from $348 round-trip. 11,206 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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
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