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Cheap flights from Chicago to Montego Bay from $175

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Montego Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:40 pm - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
$433Frontier
Thu, Oct 22 - Sat, Oct 24
Frontier Logo
6:40 pm - 2:33 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:48 pm - 11:43 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
$433Frontier
Thu, Oct 22 - Mon, Oct 26
American Airlines Logo
9:40 am - 2:52 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 12mnonstop
American Airlines Logo
3:49 pm - 7:45 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 56mnonstop
$436American Airlines
Sun, Nov 15 - Fri, Nov 20
American Airlines Logo
9:40 am - 2:52 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 12mnonstop
American Airlines Logo
3:56 pm - 7:46 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 50mnonstop
$436American Airlines
Mon, Nov 9 - Thu, Nov 12
Multiple Airlines Logo
7:15 am - 3:28 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 13m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:20 pm - 8:00 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
14h 40m2 stops Toronto Pearson Intl Ottawa
$439Multiple Airlines
Sat, Nov 14 - Mon, Nov 23
Multiple Airlines Logo
7:15 am - 3:28 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
7h 13m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:20 pm - 1:13 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
19h 53m1 stop Toronto Pearson Intl
$439Multiple Airlines
Sat, Nov 14 - Mon, Nov 23
United Airlines Logo
8:40 am - 1:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
$468United Airlines
Tue, Nov 17 - Sun, Nov 22
United Airlines Logo
8:40 am - 12:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
$468United Airlines
Mon, Oct 26 - Sun, Nov 1
JetBlue Logo
7:00 am - 2:57 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
6h 57m1 stop Fort Lauderdale
JetBlue Logo
1:07 pm - 11:36 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
11h 29m1 stop Fort Lauderdale
$472JetBlue
Tue, Nov 10 - Sat, Nov 14
JetBlue Logo
7:00 am - 2:57 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
6h 57m1 stop Fort Lauderdale
JetBlue Logo
3:00 pm - 11:38 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
9h 38m1 stop Fort Lauderdale
$472JetBlue
Tue, Nov 17 - Sun, Nov 22

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Southwest flights from Chicago to Montego Bay

Our best Southwest deals on Chicago to Montego Bay flight tickets
Southwest
Dec 1
MDW6:00 amChicago Midway
7h 25m
1 stop
MBJ2:25 pmMontego Bay Sangster Intl
Dec 8
MBJ3:45 pmMontego Bay Sangster Intl
6h 30m
1 stop
MDW9:15 pmChicago Midway
$503
Southwest
Nov 15
MDW5:05 amChicago Midway
8h 20m
1 stop
MBJ2:25 pmMontego Bay Sangster Intl
Nov 20
MBJ1:00 pmMontego Bay Sangster Intl
11h 10m
1 stop
MDW11:10 pmChicago Midway
$512
Southwest
Nov 15
MDW6:30 pmChicago Midway
16h 30m
2 stops
MBJ12:00 pmMontego Bay Sangster Intl
Nov 20
MBJ3:45 pmMontego Bay Sangster Intl
8h 15m
1 stop
MDW11:00 pmChicago Midway
$517

Air Canada flights from Chicago to Montego Bay

Our best Air Canada deals on Chicago to Montego Bay flight tickets
Air Canada
Oct 26
ORD8:45 amChicago O'Hare Intl
7h 35m
1 stop
MBJ4:20 pmMontego Bay Sangster Intl
Nov 1
MBJ1:50 pmMontego Bay Sangster Intl
29h 56m
2 stops
ORD6:46 pmChicago O'Hare Intl
$452
Air Canada
Nov 23
ORD8:45 amChicago O'Hare Intl
7h 35m
1 stop
MBJ5:20 pmMontego Bay Sangster Intl
Dec 2
MBJ6:20 pmMontego Bay Sangster Intl
22h 18m
1 stop
ORD3:38 pmChicago O'Hare Intl
$459
Air Canada
Nov 28
ORD3:40 pmChicago O'Hare Intl
20h 45m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
Dec 5
MBJ6:20 pmMontego Bay Sangster Intl
15h 48m
1 stop
ORD9:08 amChicago O'Hare Intl
$465

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

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Route

Depart

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Price

Cheapest round-trip

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 10/22

6:40 pm-2:33 pm

1 stop19h 53m

Montego Bay Sangster Intl

Sat 10/24

3:48 pm-11:43 pm

1 stop7h 55m

$433

ChicagoMontego Bay

MDW Chicago Midway - MBJ Montego Bay Sangster Intl

MDWMBJ

Chicago Midway

Thu 10/22

6:40 pm-2:33 pm

1 stop19h 53m

Montego Bay Sangster Intl

Mon 10/26

3:48 pm-11:43 pm

1 stop7h 55m

$433

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sun 11/15

9:40 am-2:52 pm

Nonstop4h 12m

Montego Bay Sangster Intl

Fri 11/20

3:49 pm-7:45 pm

Nonstop4h 56m

$436

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Mon 11/9

9:40 am-2:52 pm

Nonstop4h 12m

Montego Bay Sangster Intl

Thu 11/12

3:56 pm-7:46 pm

Nonstop4h 50m

$436

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 11/14

7:15 am-3:28 pm

1 stop7h 13m

Montego Bay Sangster Intl

Mon 11/23

6:20 pm-8:00 am

2 stops14h 40m

$439

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 11/14

7:15 am-3:28 pm

1 stop7h 13m

Montego Bay Sangster Intl

Mon 11/23

6:20 pm-1:13 pm

1 stop19h 53m

$439
Quickest round-trip

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Tue 11/17

8:40 am-1:48 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Sun 11/22

2:54 pm-6:20 pm

Nonstop4h 26m

$468

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Mon 10/26

8:40 am-12:48 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Sun 11/1

2:54 pm-6:20 pm

Nonstop4h 26m

$468

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Tue 11/10

7:00 am-2:57 pm

1 stop6h 57m

Montego Bay Sangster Intl

Sat 11/14

1:07 pm-11:36 pm

1 stop11h 29m

$472

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Tue 11/17

7:00 am-2:57 pm

1 stop6h 57m

Montego Bay Sangster Intl

Sun 11/22

3:00 pm-11:38 pm

1 stop9h 38m

$472

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 Montego Bay from

How to get the cheapest flight ticket from Chicago to Montego Bay

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 Chicago and Montego Bay?

Prices are currently typical for flights on this route.

Typical prices usually range from $401 to $749.
The lowest price recently found on this route was $433.

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of April, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $489.

What is the cheapest day to depart on your flight to Montego Bay?

On average, the least expensive day to fly to Montego Bay from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $477. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Montego Bay on Thursday is $600.

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

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

How far in advance should I book a flight from Chicago to Montego Bay?

You are more likely to see cheaper flights to Montego Bay from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Montego Bay for around $547 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Montego Bay from Chicago for as low as $462 on momondo.

What cabin class options are available on Chicago to Montego Bay flights?

There are 4 cabin classes available to choose from on Chicago to Montego Bay 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 Chicago to Montego Bay flights?

No. A direct flight is the cheapest option for a flight between Chicago to Montego Bay.

How have Chicago to Montego Bay flight prices changed over time?

As of September 2026, prices for Chicago to Montego Bay flights are approximately 30% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Montego Bay

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

Cheap Chicago to Montego Bay (CHI to MBJ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Montego Bay

Best Price Found

$175

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Montego Bay

1 airport
The best one-way flight to Montego Bay from Chicago in the past 72 hours is $175. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $433.
The fastest flight from Chicago to Montego Bay takes 3h 55m
Direct flights go from Chicago to Montego Bay every day.
There is 1 airport in Montego Bay. From Chicago there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Chicago to Montego Bay

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

    The distance between Chicago and Montego Bay Sangster Intl is about 1713.9 mi. A reasonable flight in good conditions will take 3h 55m.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Montego Bay Sangster Intl Airport.

  • What documentation or ID do you need to fly to Montego Bay Sangster Intl Airport?

    The required travel and health documents for your Montego Bay Sangster 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 Montego Bay Sangster 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 Chicago to Montego Bay?

  • What is the most popular airline from Chicago to Montego Bay?

Best airlines flying from Chicago to Montego Bay

Compare and see reviews for airlines that fly from Chicago to Montego Bay with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $144Free CancellationRating
5.6
2,568 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.8
8,610 reviews
Search Delta flights
JetBluePriceFrom $301Free CancellationRating
7.1
3,041 reviews
Search JetBlue flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
10,251 reviews
Search United Airlines flights
American AirlinesPriceFrom $315Free CancellationRating
7.0
12,096 reviews
Search American Airlines flights
SouthwestPriceFrom $467Free CancellationRating
8.0
4,200 reviews
Search Southwest flights

Traveling to a place near Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Falmouth
Lucea
Treasure Beach
Whitehouse

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Montego Bay. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Chicago to Montego Bay 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 Chicago to Montego Bay?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Montego Bay from Chicago.

I’m not ready to book a flight from Chicago to Montego Bay right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Montego Bay from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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