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Cheap flights from Chicago to Montego Bay from $165

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Montego Bay departing on 9/28. 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
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.
JetBlue Logo
7:00 am - 2:54 pm
ORD
-
MBJ
6h 54m
1 stop
JetBlue Logo
2:00 pm - 11:44 pm
MBJ
-
ORD
10h 44m
1 stop
$394JetBlue
Tue, Nov 3 - Wed, Nov 4
JetBlue Logo
7:00 am - 1:51 pm
ORD
-
MBJ
6h 51m
1 stop
JetBlue Logo
2:53 pm - 11:44 pm
MBJ
-
ORD
8h 51m
1 stop
$413JetBlue
Sat, Oct 24 - Thu, Oct 29
JetBlue Logo
7:00 am - 1:40 pm
ORD
-
MBJ
5h 40m
1 stop
JetBlue Logo
5:00 pm - 11:44 pm
MBJ
-
ORD
7h 44m
1 stop
$418JetBlue
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
9:00 am - 1:12 pm
ORD
-
MBJ
4h 12mnonstop
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
$434American Airlines
Sun, Aug 16 - Thu, Aug 20
American Airlines Logo
7:30 am - 1:34 pm
ORD
-
MBJ
6h 04m
1 stop
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
$438American Airlines
Sun, Aug 16 - Thu, Aug 20
Multiple Airlines Logo
7:00 am - 2:54 pm
ORD
-
MBJ
6h 54m
1 stop
Multiple Airlines Logo
1:50 pm - 2:52 pm
MBJ
-
ORD
26h 02m
2 stops
$441Multiple Airlines
Sun, Nov 1 - Wed, Nov 4
Southwest Logo
5:10 am - 1:30 pm
MDW
-
MBJ
8h 20m
1 stop
Southwest Logo
12:15 pm - 10:40 pm
MBJ
-
MDW
10h 25m
1 stop
$448Southwest
Sun, Aug 16 - Thu, Aug 20
Southwest Logo
5:00 am - 1:30 pm
MDW
-
MBJ
8h 30m
2 stops
Southwest Logo
12:15 pm - 10:20 pm
MBJ
-
MDW
10h 05m
2 stops
$453Southwest
Sun, Aug 16 - Thu, Aug 20
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
$472Frontier
Tue, Jul 21 - Fri, Jul 24
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:32 pm - 10:47 pm
MBJ
-
MDW
9h 15m
1 stop
$483Frontier
Sat, Aug 15 - Sat, Aug 22

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JetBlue flights from Chicago to Montego Bay

Our best JetBlue deals on Chicago to Montego Bay flight tickets
JetBlue
Nov 3
ORD7:00 amChicago O'Hare Intl
6h 54m
1 stop
MBJ2:54 pmMontego Bay Sangster Intl
Nov 4
MBJ2:00 pmMontego Bay Sangster Intl
10h 44m
1 stop
ORD11:44 pmChicago O'Hare Intl
$394
JetBlue
Oct 24
ORD7:00 amChicago O'Hare Intl
6h 51m
1 stop
MBJ1:51 pmMontego Bay Sangster Intl
Oct 29
MBJ2:53 pmMontego Bay Sangster Intl
8h 51m
1 stop
ORD11:44 pmChicago O'Hare Intl
$413
JetBlue
Dec 5
ORD7:00 amChicago O'Hare Intl
5h 40m
1 stop
MBJ1:40 pmMontego Bay Sangster Intl
Dec 12
MBJ5:00 pmMontego Bay Sangster Intl
7h 44m
1 stop
ORD11:44 pmChicago O'Hare Intl
$418

Delta flights from Chicago to Montego Bay

Our best Delta deals on Chicago to Montego Bay flight tickets
Delta
Aug 16
ORD5:30 amChicago O'Hare Intl
7h 31m
1 stop
MBJ1:01 pmMontego Bay Sangster Intl
Aug 28
MBJ4:59 pmMontego Bay Sangster Intl
16h 41m
1 stop
ORD9:40 amChicago O'Hare Intl
$448
Delta
Aug 16
ORD5:30 amChicago O'Hare Intl
7h 31m
1 stop
MBJ1:01 pmMontego Bay Sangster Intl
Aug 20
MBJ4:59 pmMontego Bay Sangster Intl
14h 57m
2 stops
ORD7:56 amChicago O'Hare Intl
$453
Delta
Aug 16
MDW6:05 amChicago Midway
6h 56m
1 stop
MBJ1:01 pmMontego Bay Sangster Intl
Aug 28
MBJ2:26 pmMontego Bay Sangster Intl
8h 10m
1 stop
MDW10:36 pmChicago Midway
$505

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Montego Bay 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 July 2, 2026.
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 11/3

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Wed 11/4

2:00 pm-11:44 pm

1 stop10h 44m

$394

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 10/24

7:00 am-1:51 pm

1 stop6h 51m

Montego Bay Sangster Intl

Thu 10/29

2:53 pm-11:44 pm

1 stop8h 51m

$413

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 12/5

7:00 am-1:40 pm

1 stop5h 40m

Montego Bay Sangster Intl

Sat 12/12

5:00 pm-11:44 pm

1 stop7h 44m

$418
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

9:00 am-1:12 pm

Nonstop4h 12m

Montego Bay Sangster Intl

Thu 8/20

2:12 pm-6:55 pm

Nonstop4h 43m

$434

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

7:30 am-1:34 pm

1 stop6h 04m

Montego Bay Sangster Intl

Thu 8/20

2:12 pm-6:55 pm

Nonstop4h 43m

$438

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 11/1

7:00 am-2:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Wed 11/4

1:50 pm-2:52 pm

2 stops26h 02m

$441

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

5:10 am-1:30 pm

1 stop8h 20m

Montego Bay Sangster Intl

Thu 8/20

12:15 pm-10:40 pm

1 stop10h 25m

$448

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

5:00 am-1:30 pm

2 stops8h 30m

Montego Bay Sangster Intl

Thu 8/20

12:15 pm-10:20 pm

2 stops10h 05m

$453

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 7/21

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Fri 7/24

1:32 pm-10:03 pm

1 stop8h 31m

$472

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/15

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Sat 8/22

1:32 pm-10:47 pm

1 stop9h 15m

$483

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?

What is the cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of August, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $127.

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 $492. 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 $619.

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 $526 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 $468 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?

You could potentially save up to 20% on your flight if you consider stops on a Chicago to Montego Bay flight.

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

As of July 2026, prices for Chicago to Montego Bay flights are approximately 6% more expensive 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

$252

Fastest flight time

3h 50m

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 $252. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $540.
The fastest flight from Chicago to Montego Bay takes 3h 50m
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 50m.

  • 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
2,850 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.8
8,452 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.1
3,008 reviews
Search JetBlue flights
United AirlinesPriceFrom $297Free CancellationRating
7.4
9,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $318Free CancellationRating
7.1
11,769 reviews
Search American Airlines flights
SouthwestPriceFrom $467Free CancellationRating
7.9
4,249 reviews
Search Southwest flights

  • American Airlines Flights From Chicago to Montego Bay

    American Airlines flight deals from Chicago to Montego Bay start from $318 round-trip. Over the 3 American Airlines flights for this route in a normal week, average airfare is usually $539 round-trip - but some users have found much cheaper deals with momondo.

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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