Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Montego Bay from $104

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 4/13. 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.

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
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
Multiple Airlines Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$295Multiple Airlines
Tue, Apr 28 - Tue, May 5
Frontier Logo
4:05 pm - 12:11 pm
ORD
-
MBJ
20h 06m
2 stops
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$307Frontier
Tue, May 5 - Tue, May 12
Frontier Logo
7:52 pm - 12:11 pm
ORD
-
MBJ
16h 19m
2 stops
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$313Frontier
Sat, May 9 - Tue, May 12
Spirit Airlines Logo
5:05 am - 12:16 pm
ORD
-
MBJ
7h 11m
1 stop
Spirit Airlines Logo
1:21 pm - 12:24 am
MBJ
-
ORD
11h 03m
1 stop
$315Spirit Airlines
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
4:05 pm - 12:11 pm
ORD
-
MBJ
20h 06m
2 stops
Frontier Logo
1:16 pm - 7:55 am
MBJ
-
ORD
18h 39m
1 stop
$317Frontier
Tue, May 5 - Mon, May 11
United Airlines Logo
8:40 am - 12:50 pm
ORD
-
MBJ
4h 10mnonstop
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
$318United Airlines
Mon, Apr 13 - Thu, Apr 23
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$318Southwest
Fri, Jul 3 - Tue, Jul 7
United Airlines Logo
8:45 am - 3:10 pm
ORD
-
MBJ
6h 25m
1 stop
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
$322United Airlines
Mon, Apr 13 - Thu, Apr 23
American Airlines Logo
6:34 am - 1:58 pm
ORD
-
MBJ
7h 24m
1 stop
American Airlines Logo
2:00 pm - 6:30 pm
MBJ
-
ORD
4h 30mnonstop
$327American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
8:05 am - 12:13 pm
ORD
-
MBJ
4h 08mnonstop
American Airlines Logo
2:29 pm - 11:54 pm
MBJ
-
ORD
9h 25m
1 stop
$328American Airlines
Mon, May 4 - Fri, May 8

Frontier flights from Chicago to Montego Bay

Our best Frontier deals on Chicago to Montego Bay flight tickets
Frontier
May 5
ORD4:05 pmChicago O'Hare Intl
20h 06m
2 stops
MBJ12:11 pmMontego Bay Sangster Intl
May 12
MBJ1:16 pmMontego Bay Sangster Intl
18h 39m
1 stop
ORD7:55 amChicago O'Hare Intl
$307
Frontier
May 9
ORD7:52 pmChicago O'Hare Intl
16h 19m
2 stops
MBJ12:11 pmMontego Bay Sangster Intl
May 12
MBJ1:16 pmMontego Bay Sangster Intl
18h 39m
1 stop
ORD7:55 amChicago O'Hare Intl
$313
Frontier
May 5
ORD4:05 pmChicago O'Hare Intl
20h 06m
2 stops
MBJ12:11 pmMontego Bay Sangster Intl
May 11
MBJ1:16 pmMontego Bay Sangster Intl
18h 39m
1 stop
ORD7:55 amChicago O'Hare Intl
$317

American Airlines flights from Chicago to Montego Bay

Our best American Airlines deals on Chicago to Montego Bay flight tickets
American Airlines
Apr 14
ORD8:05 amChicago O'Hare Intl
4h 08m
MBJ12:13 pmMontego Bay Sangster Intl
Apr 22
MBJ1:15 pmMontego Bay Sangster Intl
4h 40m
ORD5:55 pmChicago O'Hare Intl
$318
American Airlines
Apr 14
ORD5:00 amChicago O'Hare Intl
10h 37m
1 stop
MBJ3:37 pmMontego Bay Sangster Intl
Apr 22
MBJ1:15 pmMontego Bay Sangster Intl
4h 40m
ORD5:55 pmChicago O'Hare Intl
$322
American Airlines
Apr 8
ORD8:05 amChicago O'Hare Intl
4h 08m
MBJ12:13 pmMontego Bay Sangster Intl
Apr 23
MBJ1:15 pmMontego Bay Sangster Intl
4h 40m
ORD5:55 pmChicago O'Hare Intl
$323

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 31, 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 4/28

5:05 am-12:16 pm

1 stop7h 11m

Montego Bay Sangster Intl

Tue 5/5

1:16 pm-7:55 am

1 stop18h 39m

$295

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/5

4:05 pm-12:11 pm

2 stops20h 06m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-7:55 am

1 stop18h 39m

$307

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 5/9

7:52 pm-12:11 pm

2 stops16h 19m

Montego Bay Sangster Intl

Tue 5/12

1:16 pm-7:55 am

1 stop18h 39m

$313

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/21

5:05 am-12:16 pm

1 stop7h 11m

Montego Bay Sangster Intl

Tue 4/28

1:21 pm-12:24 am

1 stop11h 03m

$315

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 5/5

4:05 pm-12:11 pm

2 stops20h 06m

Montego Bay Sangster Intl

Mon 5/11

1:16 pm-7:55 am

1 stop18h 39m

$317

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 4/13

8:40 am-12:50 pm

Nonstop4h 10m

Montego Bay Sangster Intl

Thu 4/23

1:52 pm-6:15 pm

Nonstop4h 23m

$318
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 7/3

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Tue 7/7

1:50 pm-5:50 pm

Nonstop4h 00m

$318

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 4/13

8:45 am-3:10 pm

1 stop6h 25m

Montego Bay Sangster Intl

Thu 4/23

1:52 pm-6:15 pm

Nonstop4h 23m

$322

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 8/12

6:34 am-1:58 pm

1 stop7h 24m

Montego Bay Sangster Intl

Wed 8/19

2:00 pm-6:30 pm

Nonstop4h 30m

$327

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Fri 5/8

2:29 pm-11:54 pm

1 stop9h 25m

$328

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 April is also cheap. Prices for this month can be found on momondo for an average of $531.

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 $509. 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 $655.

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 $551 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 $505 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 2% 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 42% 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

$138

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 $138. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $307.
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 $141Free CancellationRating
6.3
8,566 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.7
3,009 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,365 reviews
Search Delta flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,525 reviews
Search United Airlines flights
American AirlinesPriceFrom $374Free CancellationRating
7.1
11,542 reviews
Search American Airlines flights
SouthwestPriceFrom $518Free CancellationRating
8.0
4,332 reviews
Search Southwest flights

  • United Airlines Flights From Chicago to Montego Bay

    United Airlines flight deals from Chicago to Montego Bay start from $302 round-trip. Over the 5 United Airlines flights for this route in a normal week, average airfare is usually $537 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Montego Bay

    American Airlines is also a popular choice for this route. American Airlines flight deals for Chicago to Montego Bay start from as low as $374 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $567. American Airlines operates 7 flights to Montego Bay from Chicago in an average week. Users have rated it 7.1/10 across 11,542 reviews.

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 4/30
Thu 5/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Jamaica