Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Montego Bay from $98

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 2/10. 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 Chicago to Montego Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
Multiple Airlines Logo
2:35 pm - 10:47 am
MBJ
-
ORD
21h 12m2 stops
$382Multiple Airlines
Sun, Jan 25 - Sat, Jan 31
Spirit Airlines Logo
5:32 pm - 12:02 pm
ORD
-
MBJ
17h 30m1 stop
Spirit Airlines Logo
12:57 pm - 7:38 pm
MBJ
-
ORD
7h 41m1 stop
$384Spirit Airlines
Sat, Jan 17 - Fri, Jan 23
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
Spirit Airlines Logo
12:57 pm - 11:47 pm
MBJ
-
ORD
11h 50m1 stop
$385Spirit Airlines
Thu, Feb 5 - Mon, Feb 9
Frontier Logo
4:42 pm - 8:50 am
ORD
-
MBJ
15h 08m1 stop
Frontier Logo
10:40 am - 10:39 pm
MBJ
-
ORD
12h 59m1 stop
$386Frontier
Thu, Feb 12 - Sat, Feb 21
Multiple Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m1 stop
Multiple Airlines Logo
10:32 am - 10:39 pm
MBJ
-
ORD
13h 07m1 stop
$387Multiple Airlines
Tue, Feb 10 - Sun, Feb 15
Frontier Logo
12:22 pm - 8:50 am
MDW
-
MBJ
19h 28m1 stop
Frontier Logo
10:32 am - 7:59 pm
MBJ
-
MDW
10h 27m1 stop
$394Frontier
Thu, Feb 19 - Sun, Feb 22
Southwest Logo
3:25 pm - 1:00 pm
MDW
-
MBJ
20h 35m2 stops
Southwest Logo
1:30 pm - 9:10 pm
MBJ
-
MDW
8h 40m1 stop
$421Southwest
Sun, Feb 1 - Thu, Feb 5
Delta Logo
6:14 pm - 11:13 am
MDW
-
MBJ
15h 59m1 stop
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m1 stop
$427Delta
Mon, Feb 9 - Wed, Feb 18
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
Delta Logo
2:19 pm - 10:33 pm
MBJ
-
MDW
9h 14m1 stop
$436Delta
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
5:30 am - 1:00 pm
MDW
-
MBJ
6h 30m1 stop
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m2 stops
$454Southwest
Mon, Feb 9 - Wed, Feb 18

Air Canada flights from Chicago to Montego Bay

Our best Air Canada deals on Chicago to Montego Bay flight tickets
Air Canada
Jun 5
ORD8:20 pmChicago O'Hare Intl
15h 00m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
Jun 10
MBJ12:15 pmMontego Bay Sangster Intl
19h 50m
2 stops
ORD8:05 amChicago O'Hare Intl
$384
Find similar
Air Canada
Jun 7
ORD8:20 pmChicago O'Hare Intl
15h 00m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
Jun 11
MBJ12:15 pmMontego Bay Sangster Intl
20h 45m
1 stop
ORD9:00 amChicago O'Hare Intl
$386
Find similar
Air Canada
Jun 4
ORD10:53 amChicago O'Hare Intl
24h 27m
2 stops
MBJ11:20 amMontego Bay Sangster Intl
Jun 7
MBJ12:15 pmMontego Bay Sangster Intl
20h 45m
1 stop
ORD9:00 amChicago O'Hare Intl
$396
Find similar

Spirit Airlines flights from Chicago to Montego Bay

Our best Spirit Airlines deals on Chicago to Montego Bay flight tickets
Spirit Airlines
Feb 5
ORD5:15 amChicago O'Hare Intl
5h 47m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Feb 9
MBJ12:57 pmMontego Bay Sangster Intl
11h 50m
1 stop
ORD11:47 pmChicago O'Hare Intl
$385
Find similar
Spirit Airlines
Jan 16
ORD5:15 amChicago O'Hare Intl
5h 47m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Jan 22
MBJ12:57 pmMontego Bay Sangster Intl
7h 41m
1 stop
ORD7:38 pmChicago O'Hare Intl
$388
Find similar
Spirit Airlines
Feb 8
ORD8:43 pmChicago O'Hare Intl
14h 19m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Feb 15
MBJ1:00 pmMontego Bay Sangster Intl
11h 47m
1 stop
ORD11:47 pmChicago O'Hare Intl
$391
Find similar

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 January 6, 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

Sun 1/25

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Sat 1/31

2:35 pm-10:47 am

2 stops21h 12m

$382

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/17

5:32 pm-12:02 pm

1 stop17h 30m

Montego Bay Sangster Intl

Fri 1/23

12:57 pm-7:38 pm

1 stop7h 41m

$384

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 2/5

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Mon 2/9

12:57 pm-11:47 pm

1 stop11h 50m

$385

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 2/12

4:42 pm-8:50 am

1 stop15h 08m

Montego Bay Sangster Intl

Sat 2/21

10:40 am-10:39 pm

1 stop12h 59m

$386

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/10

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Sun 2/15

10:32 am-10:39 pm

1 stop13h 07m

$387

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 2/19

12:22 pm-8:50 am

1 stop19h 28m

Montego Bay Sangster Intl

Sun 2/22

10:32 am-7:59 pm

1 stop10h 27m

$394

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/1

3:25 pm-1:00 pm

2 stops20h 35m

Montego Bay Sangster Intl

Thu 2/5

1:30 pm-9:10 pm

1 stop8h 40m

$421

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/9

6:14 pm-11:13 am

1 stop15h 59m

Montego Bay Sangster Intl

Wed 2/18

4:44 pm-10:31 pm

1 stop6h 47m

$427

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/17

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Tue 2/24

2:19 pm-10:33 pm

1 stop9h 14m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/9

5:30 am-1:00 pm

1 stop6h 30m

Montego Bay Sangster Intl

Wed 2/18

2:00 pm-10:05 pm

2 stops9h 05m

$454

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $540.

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 $557. 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 $689.

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 week ahead of your departure date. In general, you can expect to find flights to Montego Bay for around $580 when searching week 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 $497 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?

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 January 2026, prices for Chicago to Montego Bay flights are approximately 2% 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

$242

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 $242. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $432.
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

  • 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
Spirit AirlinesPriceFrom $168Free CancellationRating
6.3
8,273 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
8,017 reviews
Search Delta flights
FrontierPriceFrom $341Free CancellationRating
5.7
3,064 reviews
Search Frontier flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,132 reviews
Search United Airlines flights
American AirlinesPriceFrom $429Free CancellationRating
7.2
11,083 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,247 reviews
Search Southwest flights

  • American Airlines Flights From Chicago to Montego Bay

    American Airlines flight deals from Chicago to Montego Bay start from $429 round-trip. Over the 4 American Airlines flights for this route in a normal week, average airfare is usually $588 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.

An easier way to manage your Montego Bay 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
Thu 2/5
Thu 2/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Jamaica