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Cheap flights from Chicago to Montego Bay from $113

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 4/26. 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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Find the cheapest flights from Chicago to Montego Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
12:25 pm - 8:30 am
MBJ
-
ORD
20h 05m
1 stop
$294American Airlines
Wed, Apr 29 - Mon, May 4
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
4:37 pm - 12:11 pm
MBJ
-
ORD
19h 34m
1 stop
$295American Airlines
Sat, Apr 18 - Tue, Apr 21
American Airlines Logo
7:15 am - 1:25 pm
ORD
-
MBJ
6h 10m
1 stop
American Airlines Logo
3:20 pm - 11:34 pm
MBJ
-
ORD
8h 14m
1 stop
$297American Airlines
Thu, May 7 - Sun, May 10
United Airlines Logo
8:40 am - 12:50 pm
ORD
-
MBJ
4h 10mnonstop
United Airlines Logo
4:12 pm - 11:43 pm
MBJ
-
ORD
7h 31m
1 stop
$298United Airlines
Sat, Apr 11 - Wed, Apr 15
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$298Southwest
Fri, Jun 5 - Mon, Jun 8
Spirit Airlines Logo
5:05 am - 11:05 am
ORD
-
MBJ
6h 00m
1 stop
Spirit Airlines Logo
1:21 pm - 12:24 am
MBJ
-
ORD
11h 03m
1 stop
$301Spirit Airlines
Sun, Apr 12 - Thu, Apr 23
United Airlines Logo
8:15 pm - 1:30 pm
ORD
-
MBJ
17h 15m
1 stop
United Airlines Logo
2:40 pm - 12:45 am
MBJ
-
ORD
10h 05m
1 stop
$302United Airlines
Wed, Apr 29 - Sat, May 2
Frontier Logo
6:00 am - 12:42 pm
MDW
-
MBJ
6h 42m
1 stop
Frontier Logo
1:17 pm - 10:14 pm
MBJ
-
MDW
8h 57m
1 stop
$352Frontier
Mon, Apr 13 - Sat, Apr 25
Frontier Logo
6:00 am - 2:23 pm
MDW
-
MBJ
8h 23m
1 stop
Frontier Logo
1:17 pm - 10:14 pm
MBJ
-
MDW
8h 57m
1 stop
$373Frontier
Sun, Apr 12 - Sat, Apr 25
Southwest Logo
9:55 am - 1:45 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
12:15 pm - 10:45 pm
MBJ
-
MDW
10h 30m
2 stops
$386Southwest
Sat, Apr 11 - Thu, Apr 16

American Airlines flights from Chicago to Montego Bay

Our best American Airlines deals on Chicago to Montego Bay flight tickets
American Airlines
Apr 29
ORD8:05 amChicago O'Hare Intl
4h 08m
MBJ12:13 pmMontego Bay Sangster Intl
May 4
MBJ12:25 pmMontego Bay Sangster Intl
20h 05m
1 stop
ORD8:30 amChicago O'Hare Intl
$294
American Airlines
Apr 18
ORD8:05 amChicago O'Hare Intl
4h 08m
MBJ12:13 pmMontego Bay Sangster Intl
Apr 21
MBJ4:37 pmMontego Bay Sangster Intl
19h 34m
1 stop
ORD12:11 pmChicago O'Hare Intl
$295
American Airlines
May 7
ORD7:15 amChicago O'Hare Intl
6h 10m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
May 10
MBJ3:20 pmMontego Bay Sangster Intl
8h 14m
1 stop
ORD11:34 pmChicago O'Hare Intl
$297

Spirit Airlines flights from Chicago to Montego Bay

Our best Spirit Airlines deals on Chicago to Montego Bay flight tickets
Spirit Airlines
Apr 12
ORD5:05 amChicago O'Hare Intl
6h 00m
1 stop
MBJ11:05 amMontego Bay Sangster Intl
Apr 23
MBJ1:21 pmMontego Bay Sangster Intl
11h 03m
1 stop
ORD12:24 amChicago O'Hare Intl
$301
Spirit Airlines
May 3
ORD5:05 amChicago O'Hare Intl
7h 11m
1 stop
MBJ12:16 pmMontego Bay Sangster Intl
May 7
MBJ1:21 pmMontego Bay Sangster Intl
11h 03m
1 stop
ORD12:24 amChicago O'Hare Intl
$306
Spirit Airlines
Apr 18
ORD7:15 pmChicago O'Hare Intl
17h 01m
1 stop
MBJ12:16 pmMontego Bay Sangster Intl
Apr 21
MBJ1:21 pmMontego Bay Sangster Intl
11h 03m
1 stop
ORD12:24 amChicago O'Hare Intl
$311

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 March 4, 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

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 4/29

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Mon 5/4

12:25 pm-8:30 am

1 stop20h 05m

$294

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 4/18

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Tue 4/21

4:37 pm-12:11 pm

1 stop19h 34m

$295

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 5/7

7:15 am-1:25 pm

1 stop6h 10m

Montego Bay Sangster Intl

Sun 5/10

3:20 pm-11:34 pm

1 stop8h 14m

$297

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 4/11

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Wed 4/15

4:12 pm-11:43 pm

1 stop7h 31m

$298

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 6/5

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Mon 6/8

1:50 pm-5:50 pm

Nonstop4h 00m

$298

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/12

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

Thu 4/23

1:21 pm-12:24 am

1 stop11h 03m

$301

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 4/29

8:15 pm-1:30 pm

1 stop17h 15m

Montego Bay Sangster Intl

Sat 5/2

2:40 pm-12:45 am

1 stop10h 05m

$302

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 4/13

6:00 am-12:42 pm

1 stop6h 42m

Montego Bay Sangster Intl

Sat 4/25

1:17 pm-10:14 pm

1 stop8h 57m

$352

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 4/12

6:00 am-2:23 pm

1 stop8h 23m

Montego Bay Sangster Intl

Sat 4/25

1:17 pm-10:14 pm

1 stop8h 57m

$373

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/11

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Thu 4/16

12:15 pm-10:45 pm

2 stops10h 30m

$386

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 cheapest month to fly to Montego Bay?

If you aren’t able to travel to Montego Bay during the month of January, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $529.

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 $539. 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 $676.

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 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 $564 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 $494 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to Montego Bay Sangster Intl 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 21% 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 March 2026, prices for Chicago to Montego Bay flights are approximately 35% 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

$218

Fastest flight time

3h 45m

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 $218. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $386.
The fastest flight from Chicago to Montego Bay takes 3h 45m
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

  • 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 45m.

  • 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
Spirit AirlinesPriceFrom $141Free CancellationRating
6.3
8,490 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,245 reviews
Search Delta flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,382 reviews
Search United Airlines flights
American AirlinesPriceFrom $393Free CancellationRating
7.1
11,379 reviews
Search American Airlines flights
SouthwestPriceFrom $518Free CancellationRating
8.0
4,304 reviews
Search Southwest flights

  • American Airlines Flights From Chicago to Montego Bay

    American Airlines flight deals from Chicago to Montego Bay start from $393 round-trip. Over the 6 American Airlines flights for this route in a normal week, average airfare is usually $569 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
Lucea
Falmouth
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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