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Cheap flights from Chicago to Montego Bay from $138

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 8/31. 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

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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.
JetBlue Logo
7:00 am - 2:54 pm
ORD
-
MBJ
6h 54m
1 stop
JetBlue Logo
3:59 pm - 11:44 pm
MBJ
-
ORD
8h 45m
1 stop
$346JetBlue
Tue, Nov 3 - Tue, Nov 10
American Airlines Logo
5:00 am - 12:42 pm
ORD
-
MBJ
6h 42m
1 stop
American Airlines Logo
3:14 pm - 6:55 pm
MBJ
-
ORD
4h 41mnonstop
$347American Airlines
Wed, Nov 18 - Wed, Nov 25
JetBlue Logo
7:00 am - 2:54 pm
ORD
-
MBJ
6h 54m
1 stop
JetBlue Logo
3:59 pm - 11:44 pm
MBJ
-
ORD
8h 45m
1 stop
$348JetBlue
Tue, Nov 3 - Tue, Nov 10
Delta Logo
6:40 am - 1:01 pm
ORD
-
MBJ
6h 21m
1 stop
Delta Logo
4:59 pm - 12:02 am
MBJ
-
ORD
7h 03m
1 stop
$352Delta
Sun, Aug 16 - Thu, Aug 20
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
$352Delta
Sun, Aug 30 - Wed, Sep 2
Delta Logo
9:30 am - 3:34 pm
ORD
-
MBJ
6h 04m
1 stop
Delta Logo
4:59 pm - 8:00 am
MBJ
-
ORD
15h 01m
2 stops
$357Delta
Mon, Oct 19 - Thu, Oct 22
Delta Logo
6:00 am - 12:07 pm
MDW
-
MBJ
6h 07m
1 stop
Delta Logo
1:32 pm - 8:45 am
MBJ
-
MDW
19h 13m
2 stops
$357Delta
Tue, Oct 13 - Thu, Oct 15
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
$452Frontier
Tue, Jun 30 - Wed, Jul 8
Southwest Logo
10:10 am - 2:00 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
2:30 pm - 11:15 pm
MBJ
-
MDW
8h 45m
1 stop
$456Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
5:05 am - 1:30 pm
MDW
-
MBJ
8h 25m
1 stop
Southwest Logo
2:20 pm - 10:05 pm
MBJ
-
MDW
7h 45m
1 stop
$457Southwest
Sat, Jul 25 - Wed, Jul 29

Delta flights from Chicago to Montego Bay

Our best Delta deals on Chicago to Montego Bay flight tickets
Delta
Aug 30
MDW6:05 amChicago Midway
9h 29m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
Sep 2
MBJ1:09 pmMontego Bay Sangster Intl
9h 27m
1 stop
MDW10:36 pmChicago Midway
$352
Delta
Oct 13
MDW6:00 amChicago Midway
6h 07m
1 stop
MBJ12:07 pmMontego Bay Sangster Intl
Oct 15
MBJ1:32 pmMontego Bay Sangster Intl
19h 13m
2 stops
MDW8:45 amChicago Midway
$357
Delta
Sep 8
MDW6:00 amChicago Midway
5h 49m
1 stop
MBJ11:49 amMontego Bay Sangster Intl
Sep 12
MBJ2:35 pmMontego Bay Sangster Intl
7h 11m
1 stop
MDW9:46 pmChicago Midway
$399

Frontier flights from Chicago to Montego Bay

Our best Frontier deals on Chicago to Montego Bay flight tickets
Frontier
Jun 30
MDW6:00 amChicago Midway
6h 21m
1 stop
MBJ12:21 pmMontego Bay Sangster Intl
Jul 8
MBJ1:32 pmMontego Bay Sangster Intl
8h 31m
1 stop
MDW10:03 pmChicago Midway
$452
Frontier
Jul 28
MDW6:05 amChicago Midway
6h 22m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Aug 2
MBJ1:39 pmMontego Bay Sangster Intl
8h 24m
1 stop
MDW10:03 pmChicago Midway
$463
Frontier
Aug 21
MDW6:00 amChicago Midway
6h 21m
1 stop
MBJ12:21 pmMontego Bay Sangster Intl
Aug 25
MBJ1:26 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW10:11 pmChicago Midway
$472

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 June 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

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

Tue 11/10

3:59 pm-11:44 pm

1 stop8h 45m

$346
Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/18

5:00 am-12:42 pm

1 stop6h 42m

Montego Bay Sangster Intl

Wed 11/25

3:14 pm-6:55 pm

Nonstop4h 41m

$347

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

Tue 11/10

3:59 pm-11:44 pm

1 stop8h 45m

$348

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

6:40 am-1:01 pm

1 stop6h 21m

Montego Bay Sangster Intl

Thu 8/20

4:59 pm-12:02 am

1 stop7h 03m

$352

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/30

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Wed 9/2

1:09 pm-10:36 pm

1 stop9h 27m

$352

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 10/19

9:30 am-3:34 pm

1 stop6h 04m

Montego Bay Sangster Intl

Thu 10/22

4:59 pm-8:00 am

2 stops15h 01m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 10/13

6:00 am-12:07 pm

1 stop6h 07m

Montego Bay Sangster Intl

Thu 10/15

1:32 pm-8:45 am

2 stops19h 13m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 6/30

6:00 am-12:21 pm

1 stop6h 21m

Montego Bay Sangster Intl

Wed 7/8

1:32 pm-10:03 pm

1 stop8h 31m

$452

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/4

10:10 am-2:00 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Sat 7/11

2:30 pm-11:15 pm

1 stop8h 45m

$456

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/25

5:05 am-1:30 pm

1 stop8h 25m

Montego Bay Sangster Intl

Wed 7/29

2:20 pm-10:05 pm

1 stop7h 45m

$457

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 June is also cheap. Prices for this month can be found on momondo for an average of $119.

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 $495. 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 $642.

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 $531 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 $465 on momondo.

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

There are 2 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 14% 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 June 2026, prices for Chicago to Montego Bay flights are approximately 4% 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

$148

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 $148. The best round-trip flight deal from Chicago to Montego Bay found on momondo in the last 72 hours is $408.
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
2,914 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.8
8,396 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.1
2,982 reviews
Search JetBlue flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,774 reviews
Search United Airlines flights
American AirlinesPriceFrom $319Free CancellationRating
7.1
11,642 reviews
Search American Airlines flights
SouthwestPriceFrom $467Free CancellationRating
8.0
4,255 reviews
Search Southwest flights

  • American Airlines Flights From Chicago to Montego Bay

    American Airlines flight deals from Chicago to Montego Bay start from $319 round-trip. Over the 2 American Airlines flights for this route in a normal week, average airfare is usually $542 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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