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 10/4. 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

Spirit Airlines Logo
12:10 pm - 10:48 pmMBJ-ORD
10h 38m1 stop
Spirit Airlines Logo
7:43 pm - 11:00 amORD-MBJ
15h 17m1 stop
$223Spirit Airlines
Find Deal
sáb., oct. 4 - sáb., oct. 11
Spirit Airlines Logo
12:09 pm - 6:38 pmMBJ-ORD
6h 29m1 stop
Spirit Airlines Logo
7:43 pm - 11:00 amORD-MBJ
15h 17m1 stop
$226Spirit Airlines
Find Deal
mié., oct. 8 - sáb., oct. 11
Frontier Logo
3:51 pm - 11:46 pmMBJ-MDW
7h 55m1 stop
Frontier Logo
1:37 pm - 2:15 pmMDW-MBJ
24h 38m1 stop
$276Frontier
Find Deal
vie., oct. 24 - vie., oct. 31
American Airlines Logo
1:50 pm - 6:23 pmMBJ-ORD
4h 33mnonstop
American Airlines Logo
9:45 pm - 2:15 pmORD-MBJ
16h 30m1 stop
$304American Airlines
Find Deal
mar., oct. 7 - sáb., oct. 11
Frontier Logo
4:01 pm - 11:20 pmMBJ-MDW
31h 19m2 stops
Frontier Logo
1:37 pm - 3:15 pmMDW-MBJ
25h 38m1 stop
$309Frontier
Find Deal
sáb., oct. 25 - sáb., nov. 1
American Airlines Logo
1:45 pm - 8:26 pmMBJ-ORD
7h 41m1 stop
American Airlines Logo
10:15 am - 3:22 pmORD-MBJ
4h 07mnonstop
$310American Airlines
Find Deal
mié., dic. 10 - lun., dic. 15
United Airlines Logo
1:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$317United Airlines
Find Deal
dom., oct. 26 - dom., nov. 2
United Airlines Logo
2:20 pm - 7:41 amMBJ-ORD
17h 21m1 stop
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
$328United Airlines
Find Deal
dom., oct. 26 - dom., nov. 2
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
Southwest Logo
6:15 am - 12:50 pmMDW-MBJ
6h 35m1 stop
$334Southwest
Find Deal
vie., oct. 24 - vie., oct. 31
Southwest Logo
1:00 pm - 9:05 pmMBJ-MDW
9h 05m1 stop
Southwest Logo
5:05 am - 2:55 pmMDW-MBJ
8h 50m1 stop
$436Southwest
Find Deal
mié., dic. 10 - lun., dic. 15

Spirit Airlines flights from Montego Bay to Chicago

Our best Spirit Airlines deals on Montego Bay to Chicago flight tickets
Spirit Airlines
Oct 4
MBJ12:10 pmMontego Bay Sangster Intl
10h 38m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 11
ORD7:43 pmChicago O'Hare Intl
15h 17m
1 stop
MBJ11:00 amMontego Bay Sangster Intl
$223
Find similar
Spirit Airlines
Oct 8
MBJ12:09 pmMontego Bay Sangster Intl
6h 29m
1 stop
ORD6:38 pmChicago O'Hare Intl
Oct 11
ORD7:43 pmChicago O'Hare Intl
15h 17m
1 stop
MBJ11:00 amMontego Bay Sangster Intl
$226
Find similar
Spirit Airlines
Sep 24
MBJ12:10 pmMontego Bay Sangster Intl
10h 38m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 29
ORD6:44 pmChicago O'Hare Intl
16h 21m
1 stop
MBJ11:05 amMontego Bay Sangster Intl
$231
Find similar

American Airlines flights from Montego Bay to Chicago

Our best American Airlines deals on Montego Bay to Chicago flight tickets
American Airlines
Oct 7
MBJ1:50 pmMontego Bay Sangster Intl
4h 33m
ORD6:23 pmChicago O'Hare Intl
Oct 11
ORD9:45 pmChicago O'Hare Intl
16h 30m
1 stop
MBJ2:15 pmMontego Bay Sangster Intl
$304
Find similar
American Airlines
Dec 10
MBJ1:45 pmMontego Bay Sangster Intl
7h 41m
1 stop
ORD8:26 pmChicago O'Hare Intl
Dec 15
ORD10:15 amChicago O'Hare Intl
4h 07m
MBJ3:22 pmMontego Bay Sangster Intl
$310
Find similar
American Airlines
Dec 12
MBJ2:30 pmMontego Bay Sangster Intl
4h 47m
ORD6:17 pmChicago O'Hare Intl
Jan 2
ORD8:11 amChicago O'Hare Intl
4h 10m
MBJ1:21 pmMontego Bay Sangster Intl
$343
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 septiembre 11, 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

sáb. 10/4

12:10 pm-10:48 pm

1 stop10h 38m

Chicago O'Hare Intl

sáb. 10/11

7:43 pm-11:00 am

1 stop15h 17m

$223

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mié. 10/8

12:09 pm-6:38 pm

1 stop6h 29m

Chicago O'Hare Intl

sáb. 10/11

7:43 pm-11:00 am

1 stop15h 17m

$226

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

vie. 10/24

3:51 pm-11:46 pm

1 stop7h 55m

Chicago Midway

vie. 10/31

1:37 pm-2:15 pm

1 stop24h 38m

$276

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 10/7

1:50 pm-6:23 pm

Nonstop4h 33m

Chicago O'Hare Intl

sáb. 10/11

9:45 pm-2:15 pm

1 stop16h 30m

$304

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

sáb. 10/25

4:01 pm-11:20 pm

2 stops31h 19m

Chicago Midway

sáb. 11/1

1:37 pm-3:15 pm

1 stop25h 38m

$309

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mié. 12/10

1:45 pm-8:26 pm

1 stop7h 41m

Chicago O'Hare Intl

lun. 12/15

10:15 am-3:22 pm

Nonstop4h 07m

$310

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

dom. 10/26

1:48 pm-6:13 pm

Nonstop4h 25m

Chicago O'Hare Intl

dom. 11/2

8:42 am-1:46 pm

Nonstop4h 04m

$317

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

dom. 10/26

2:20 pm-7:41 am

1 stop17h 21m

Chicago O'Hare Intl

dom. 11/2

8:42 am-1:46 pm

Nonstop4h 04m

$328

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

vie. 10/24

12:50 pm-8:40 pm

2 stops7h 50m

Chicago Midway

vie. 10/31

6:15 am-12:50 pm

1 stop6h 35m

$334

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

mié. 12/10

1:00 pm-9:05 pm

1 stop9h 05m

Chicago Midway

lun. 12/15

5:05 am-2:55 pm

1 stop8h 50m

$436

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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Montego Bay, with most prices found around $351. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Montego Bay to Chicago during August average around $400.

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 $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 $489. In contrast, the most expensive time of day to depart to Chicago is at noon 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 Midway 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 4 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 September 2025, prices for Montego Bay to Chicago flights are approximately 25% 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

$297

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 $297. The best round-trip flight deal from Montego Bay to Chicago found on momondo in the last 72 hours is $446.
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 25m 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
8,023 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $348Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $392Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
United AirlinesPriceFrom $409Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights

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
Lansing
Portage
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
sáb. 10/11
sáb. 10/18
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