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Cheap flights from Montego Bay to Chicago from $161

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 11/8. 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

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Cheap round-trip flights

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Spirit Airlines Logo
12:09 pm - 6:38 pmMBJ-ORD
6h 29m1 stop
Spirit Airlines Logo
5:10 am - 12:02 pmORD-MBJ
5h 52m1 stop
$255Spirit Airlines
Find Deal
Wed, Oct 29 - Sun, Nov 2
Spirit Airlines Logo
1:07 pm - 8:27 pmMBJ-ORD
8h 20m1 stop
Spirit Airlines Logo
3:26 pm - 12:02 pmORD-MBJ
19h 36m1 stop
$308Spirit Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$320United Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
United Airlines Logo
1:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
5:00 am - 1:05 pmORD-MBJ
7h 05m1 stop
$325United Airlines
Find Deal
Wed, Oct 29 - Sun, Nov 2
Delta Logo
2:17 pm - 11:40 pmMBJ-MDW
10h 23m1 stop
Delta Logo
6:00 am - 12:52 pmMDW-MBJ
5h 52m1 stop
$326Delta
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
3:30 pm - 11:29 pmMBJ-ORD
7h 59m1 stop
Frontier Logo
6:00 am - 3:15 pmORD-MBJ
8h 15m1 stop
$334Frontier
Find Deal
Sat, Nov 1 - Sat, Nov 15
Frontier Logo
11:17 am - 6:04 pmMBJ-MDW
7h 47m1 stop
Frontier Logo
6:00 am - 3:46 pmMDW-MBJ
8h 46m1 stop
$340Frontier
Find Deal
Sun, Dec 14 - Sat, Jan 10
Delta Logo
5:59 pm - 12:01 amMBJ-ORD
7h 02m1 stop
Delta Logo
6:45 am - 4:34 pmORD-MBJ
8h 49m2 stops
$351Delta
Find Deal
Thu, Nov 13 - Mon, Nov 17
Multiple Airlines Logo
1:07 pm - 8:27 pmMBJ-ORD
8h 20m1 stop
Multiple Airlines Logo
6:30 pm - 12:02 pmORD-MBJ
16h 32m2 stops
$353Multiple Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
Multiple Airlines Logo
3:30 pm - 11:29 pmMBJ-ORD
7h 59m1 stop
Multiple Airlines Logo
7:34 pm - 3:15 pmORD-MBJ
18h 41m2 stops
$362Multiple Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 15

Spirit Airlines flights from Montego Bay to Chicago

Our best Spirit Airlines deals on Montego Bay to Chicago flight tickets
Spirit Airlines
Oct 29
MBJ12:09 pmMontego Bay Sangster Intl
6h 29m
1 stop
ORD6:38 pmChicago O'Hare Intl
Nov 2
ORD5:10 amChicago O'Hare Intl
5h 52m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
$255
Find similar
Spirit Airlines
Nov 13
MBJ1:07 pmMontego Bay Sangster Intl
8h 20m
1 stop
ORD8:27 pmChicago O'Hare Intl
Nov 17
ORD3:26 pmChicago O'Hare Intl
19h 36m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
$308
Find similar
Spirit Airlines
Oct 18
MBJ12:09 pmMontego Bay Sangster Intl
11h 36m
1 stop
ORD11:45 pmChicago O'Hare Intl
Oct 20
ORD7:43 pmChicago O'Hare Intl
15h 17m
1 stop
MBJ11:00 amMontego Bay Sangster Intl
$318
Find similar

United Airlines flights from Montego Bay to Chicago

Our best United Airlines deals on Montego Bay to Chicago flight tickets
United Airlines
Nov 13
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
Nov 17
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
$320
Find similar
United Airlines
Oct 29
MBJ1:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
Nov 2
ORD5:00 amChicago O'Hare Intl
7h 05m
1 stop
MBJ1:05 pmMontego Bay Sangster Intl
$325
Find similar
United Airlines
Dec 12
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
Jan 2
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
$345
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 October 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

Wed 10/29

12:09 pm-6:38 pm

1 stop6h 29m

Chicago O'Hare Intl

Sun 11/2

5:10 am-12:02 pm

1 stop5h 52m

$255

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/13

1:07 pm-8:27 pm

1 stop8h 20m

Chicago O'Hare Intl

Mon 11/17

3:26 pm-12:02 pm

1 stop19h 36m

$308

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/13

2:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Mon 11/17

8:42 am-1:46 pm

Nonstop4h 04m

$320

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 10/29

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

Sun 11/2

5:00 am-1:05 pm

1 stop7h 05m

$325

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 11/13

2:17 pm-11:40 pm

1 stop10h 23m

Chicago Midway

Mon 11/17

6:00 am-12:52 pm

1 stop5h 52m

$326

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 11/1

3:30 pm-11:29 pm

1 stop7h 59m

Chicago O'Hare Intl

Sat 11/15

6:00 am-3:15 pm

1 stop8h 15m

$334

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Sun 12/14

11:17 am-6:04 pm

1 stop7h 47m

Chicago Midway

Sat 1/10

6:00 am-3:46 pm

1 stop8h 46m

$340

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/13

5:59 pm-12:01 am

1 stop7h 02m

Chicago O'Hare Intl

Mon 11/17

6:45 am-4:34 pm

2 stops8h 49m

$351

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 11/13

1:07 pm-8:27 pm

1 stop8h 20m

Chicago O'Hare Intl

Mon 11/17

6:30 pm-12:02 pm

2 stops16h 32m

$353

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 11/1

3:30 pm-11:29 pm

1 stop7h 59m

Chicago O'Hare Intl

Sat 11/15

7:34 pm-3:15 pm

2 stops18h 41m

$362

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 $447. 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 $491. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $508.

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 October 2025, prices for Montego Bay to Chicago flights are approximately 4% 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

$217

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 $217. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $339.
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
8,093 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,235 reviews
Search Southwest flights
United AirlinesPriceFrom $409Free CancellationRating
7.4
8,973 reviews
Search United 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 $479, with the best American Airlines deals starting from $348 round-trip. 11,043 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