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Cheap flights from Montego Bay to Chicago from $157

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 2/24. 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
12:57 pm - 7:38 pm
MBJ
-
ORD
7h 41m1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$263Spirit Airlines
Thu, Jan 22 - Mon, Jan 26
Multiple Airlines Logo
12:57 pm - 8:30 pm
MBJ
-
ORD
8h 33m1 stop
Multiple Airlines Logo
7:30 am - 12:02 pm
ORD
-
MBJ
27h 32m1 stop
$282Multiple Airlines
Thu, Jan 8 - Sun, Jan 11
Spirit Airlines Logo
12:57 pm - 7:38 pm
MBJ
-
ORD
7h 41m1 stop
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
$291Spirit Airlines
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
12:57 pm - 8:30 pm
MBJ
-
ORD
8h 33m1 stop
Multiple Airlines Logo
5:32 pm - 12:02 pm
ORD
-
MBJ
17h 30m1 stop
$295Multiple Airlines
Thu, Jan 8 - Sat, Jan 17
Frontier Logo
3:47 pm - 1:21 pm
MBJ
-
MDW
22h 34m1 stop
Frontier Logo
6:33 pm - 2:29 pm
MDW
-
MBJ
18h 56m1 stop
$307Frontier
Tue, Dec 23 - Thu, Jan 1
Frontier Logo
4:51 pm - 11:25 pm
MBJ
-
MDW
7h 34m1 stop
Frontier Logo
6:00 am - 3:31 pm
MDW
-
MBJ
8h 31m1 stop
$324Frontier
Thu, Feb 26 - Thu, Mar 5
Delta Logo
8:00 am - 5:26 pm
MBJ
-
MDW
10h 26m2 stops
Delta Logo
9:50 am - 8:41 pm
MDW
-
MBJ
9h 51m1 stop
$362Delta
Wed, Dec 24 - Tue, Dec 30
Delta Logo
8:00 am - 4:20 pm
MBJ
-
MDW
9h 20m1 stop
Delta Logo
6:00 am - 8:41 pm
MDW
-
MBJ
13h 41m1 stop
$434Delta
Sun, Dec 21 - Sun, Jan 4
Southwest Logo
12:55 pm - 10:40 pm
MBJ
-
MDW
9h 45m1 stop
Southwest Logo
6:30 am - 2:05 pm
MDW
-
MBJ
7h 35m1 stop
$451Southwest
Wed, Apr 1 - Mon, Apr 6
Southwest Logo
12:55 pm - 10:40 pm
MBJ
-
MDW
9h 45m1 stop
Southwest Logo
9:00 pm - 1:55 pm
MDW
-
MBJ
16h 55m2 stops
$482Southwest
Wed, Apr 1 - Mon, Apr 6

Spirit Airlines flights from Montego Bay to Chicago

Our best Spirit Airlines deals on Montego Bay to Chicago flight tickets
Spirit Airlines
Dec 9
MBJ1:05 pmMontego Bay Sangster Intl
12h 04m
1 stop
ORD12:09 amChicago O'Hare Intl
Jan 6
ORD5:00 amChicago O'Hare Intl
6h 05m
1 stop
MBJ12:05 pmMontego Bay Sangster Intl
$255
Find similar
Spirit Airlines
Jan 22
MBJ12:57 pmMontego Bay Sangster Intl
7h 41m
1 stop
ORD7:38 pmChicago O'Hare Intl
Jan 26
ORD5:15 amChicago O'Hare Intl
5h 47m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
$263
Find similar
Spirit Airlines
Dec 11
MBJ1:05 pmMontego Bay Sangster Intl
7h 56m
1 stop
ORD8:01 pmChicago O'Hare Intl
Jan 6
ORD5:00 amChicago O'Hare Intl
6h 05m
1 stop
MBJ12:05 pmMontego Bay Sangster Intl
$282
Find similar

Air Canada flights from Montego Bay to Chicago

Our best Air Canada deals on Montego Bay to Chicago flight tickets
Air Canada
Dec 10
MBJ2:15 pmMontego Bay Sangster Intl
19h 58m
1 stop
ORD9:13 amChicago O'Hare Intl
Jan 14
ORD8:45 pmChicago O'Hare Intl
14h 45m
1 stop
MBJ12:30 pmMontego Bay Sangster Intl
$361
Find similar
Air Canada
Jan 22
MBJ1:30 pmMontego Bay Sangster Intl
29h 18m
1 stop
ORD5:48 pmChicago O'Hare Intl
Jan 26
ORD1:55 pmChicago O'Hare Intl
21h 35m
2 stops
MBJ12:30 pmMontego Bay Sangster Intl
$374
Find similar
Air Canada
Jan 22
MBJ1:30 pmMontego Bay Sangster Intl
9h 35m
1 stop
ORD10:05 pmChicago O'Hare Intl
Jan 26
ORD9:15 pmChicago O'Hare Intl
14h 15m
1 stop
MBJ12:30 pmMontego Bay Sangster Intl
$375
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 December 4, 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

Thu 1/22

12:57 pm-7:38 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 1/26

5:15 am-12:02 pm

1 stop5h 47m

$263

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/8

12:57 pm-8:30 pm

1 stop8h 33m

Chicago O'Hare Intl

Sun 1/11

7:30 am-12:02 pm

1 stop27h 32m

$282

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/8

12:57 pm-7:38 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 1/12

5:15 am-12:02 pm

1 stop5h 47m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 1/8

12:57 pm-8:30 pm

1 stop8h 33m

Chicago O'Hare Intl

Sat 1/17

5:32 pm-12:02 pm

1 stop17h 30m

$295

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Tue 12/23

3:47 pm-1:21 pm

1 stop22h 34m

Chicago Midway

Thu 1/1

6:33 pm-2:29 pm

1 stop18h 56m

$307

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 2/26

4:51 pm-11:25 pm

1 stop7h 34m

Chicago Midway

Thu 3/5

6:00 am-3:31 pm

1 stop8h 31m

$324

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 12/24

8:00 am-5:26 pm

2 stops10h 26m

Chicago Midway

Tue 12/30

9:50 am-8:41 pm

1 stop9h 51m

$362

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 12/21

8:00 am-4:20 pm

1 stop9h 20m

Chicago Midway

Sun 1/4

6:00 am-8:41 pm

1 stop13h 41m

$434

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 4/1

12:55 pm-10:40 pm

1 stop9h 45m

Chicago Midway

Mon 4/6

6:30 am-2:05 pm

1 stop7h 35m

$451

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 4/1

12:55 pm-10:40 pm

1 stop9h 45m

Chicago Midway

Mon 4/6

9:00 pm-1:55 pm

2 stops16h 55m

$482

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 typical price of a round-trip flight between Montego Bay and Chicago?

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 $433. 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 $543.

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 $498.

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?

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 December 2025, prices for Montego Bay to Chicago flights are approximately 17% 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

$257

Fastest flight time

4h 37m

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 $257. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $387.
The fastest flight from Montego Bay to Chicago takes 4h 37m
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 39m 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
8,159 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,046 reviews
Search American Airlines flights
United AirlinesPriceFrom $349Free CancellationRating
7.4
9,066 reviews
Search United Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,255 reviews
Search Southwest 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 $476, with the best American Airlines deals starting from $348 round-trip. 11,045 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
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.

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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