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Cheap flights from Chicago to Jamaica from $111

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 Jamaica departing on 2/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
12:44 pm - 12:02 pm
ORD
-
MBJ
22h 18m
3 stops
Spirit Airlines Logo
11:57 am - 7:11 pm
MBJ
-
ORD
7h 14m
1 stop
$364Spirit Airlines
Tue, Mar 3 - Tue, Mar 10
Multiple Airlines Logo
4:28 pm - 12:12 pm
ORD
-
MBJ
19h 44m
1 stop
Multiple Airlines Logo
12:00 pm - 11:41 pm
MBJ
-
ORD
11h 41m
1 stop
$365Multiple Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
6:05 am - 1:25 pm
ORD
-
MBJ
7h 20m
1 stop
American Airlines Logo
4:37 pm - 12:25 am
MBJ
-
ORD
7h 48m
1 stop
$366American Airlines
Thu, Apr 16 - Wed, Apr 22
American Airlines Logo
8:05 am - 12:11 pm
ORD
-
MBJ
4h 06mnonstop
American Airlines Logo
1:14 pm - 5:55 pm
MBJ
-
ORD
4h 41mnonstop
$371American Airlines
Sun, Mar 8 - Sat, Mar 14
Southwest Logo
9:55 am - 1:45 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
2:55 pm - 10:20 pm
MBJ
-
MDW
7h 25m
1 stop
$372Southwest
Sat, Apr 18 - Thu, Apr 23
Southwest Logo
6:30 am - 2:30 pm
MDW
-
MBJ
8h 00m
1 stop
Southwest Logo
12:30 pm - 4:50 pm
MBJ
-
MDW
4h 20mnonstop
$375Southwest
Wed, Mar 11 - Sun, Mar 15
Frontier Logo
6:55 am - 2:17 pm
MDW
-
MBJ
7h 22m
1 stop
Frontier Logo
9:01 am - 8:07 pm
MBJ
-
MDW
11h 06m
1 stop
$382Frontier
Sat, Mar 14 - Sat, Apr 11
Delta Logo
6:00 am - 3:28 pm
MDW
-
MBJ
9h 28m
1 stop
Delta Logo
1:38 pm - 10:31 pm
MBJ
-
MDW
8h 53m
1 stop
$388Delta
Wed, Mar 11 - Wed, Mar 18
Delta Logo
6:00 am - 12:54 pm
MDW
-
MBJ
6h 54m
1 stop
Delta Logo
2:09 pm - 10:28 pm
MBJ
-
MDW
8h 19m
1 stop
$389Delta
Wed, Apr 29 - Sat, May 2
Frontier Logo
6:00 am - 9:17 am
MDW
-
MBJ
26h 17m
1 stop
Frontier Logo
12:40 pm - 9:39 pm
MBJ
-
MDW
9h 59m
1 stop
$392Frontier
Sat, Feb 21 - Sat, Feb 28

Spirit Airlines flights from Chicago to Jamaica

Our best Spirit Airlines deals on Chicago to Jamaica flight tickets
Spirit Airlines
Mar 3
ORD12:44 pmChicago O'Hare Intl
22h 18m
3 stops
MBJ12:02 pmMontego Bay Sangster Intl
Mar 10
MBJ11:57 amMontego Bay Sangster Intl
7h 14m
1 stop
ORD7:11 pmChicago O'Hare Intl
$364
Spirit Airlines
Mar 1
ORD8:42 pmChicago O'Hare Intl
14h 20m
2 stops
MBJ12:02 pmMontego Bay Sangster Intl
Mar 6
MBJ1:00 pmMontego Bay Sangster Intl
11h 47m
1 stop
ORD11:47 pmChicago O'Hare Intl
$367
Spirit Airlines
Feb 27
ORD8:16 pmChicago O'Hare Intl
14h 46m
1 stop
MBJ12:02 pmMontego Bay Sangster Intl
Mar 2
MBJ1:00 pmMontego Bay Sangster Intl
23h 22m
1 stop
ORD11:22 amChicago O'Hare Intl
$369

Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets
Southwest
Apr 18
MDW9:55 amChicago Midway
3h 50m
MBJ1:45 pmMontego Bay Sangster Intl
Apr 23
MBJ2:55 pmMontego Bay Sangster Intl
7h 25m
1 stop
MDW10:20 pmChicago Midway
$372
Southwest
Mar 11
MDW6:30 amChicago Midway
8h 00m
1 stop
MBJ2:30 pmMontego Bay Sangster Intl
Mar 15
MBJ12:30 pmMontego Bay Sangster Intl
4h 20m
MDW4:50 pmChicago Midway
$375
Southwest
Apr 18
MDW6:10 amChicago Midway
7h 20m
1 stop
MBJ1:30 pmMontego Bay Sangster Intl
Apr 23
MBJ12:15 pmMontego Bay Sangster Intl
6h 45m
1 stop
MDW7:00 pmChicago Midway
$376

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica 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 February 11, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/3

12:44 pm-12:02 pm

3 stops22h 18m

Montego Bay Sangster Intl

Tue 3/10

11:57 am-7:11 pm

1 stop7h 14m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 4/17

4:28 pm-12:12 pm

1 stop19h 44m

Montego Bay Sangster Intl

Tue 4/21

12:00 pm-11:41 pm

1 stop11h 41m

$365

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/16

6:05 am-1:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Wed 4/22

4:37 pm-12:25 am

1 stop7h 48m

$366

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/8

8:05 am-12:11 pm

Nonstop4h 06m

Montego Bay Sangster Intl

Sat 3/14

1:14 pm-5:55 pm

Nonstop4h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 4/18

9:55 am-1:45 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Thu 4/23

2:55 pm-10:20 pm

1 stop7h 25m

$372

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 3/11

6:30 am-2:30 pm

1 stop8h 00m

Montego Bay Sangster Intl

Sun 3/15

12:30 pm-4:50 pm

Nonstop4h 20m

$375

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 3/14

6:55 am-2:17 pm

1 stop7h 22m

Montego Bay Sangster Intl

Sat 4/11

9:01 am-8:07 pm

1 stop11h 06m

$382

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 3/11

6:00 am-3:28 pm

1 stop9h 28m

Montego Bay Sangster Intl

Wed 3/18

1:38 pm-10:31 pm

1 stop8h 53m

$388

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/29

6:00 am-12:54 pm

1 stop6h 54m

Montego Bay Sangster Intl

Sat 5/2

2:09 pm-10:28 pm

1 stop8h 19m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/21

6:00 am-9:17 am

1 stop26h 17m

Montego Bay Sangster Intl

Sat 2/28

12:40 pm-9:39 pm

1 stop9h 59m

$392

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 Jamaica from

How to get the cheapest flight ticket from Chicago to Jamaica

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 Jamaica?

The cheapest month to fly to Jamaica from Chicago is in January. Flight prices, which tend to average around $516, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica 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 Jamaica?

The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $539. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $675.

What is the cheapest Chicago to Jamaica flight route?

Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago - Jamaica flight prices

How far in advance should I book a flight to Jamaica?

You are more likely to see cheaper flights to Jamaica from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $568 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Chicago for as low as $493 on momondo.

What cabin class options are available on Chicago to Jamaica flights?

There are 3 cabin classes available to choose from on Chicago to Jamaica 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 Jamaica flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago to Jamaica flight.

Cheap Chicago to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Jamaica

Best Price Found

$224

Fastest flight time

3h 45m

Direct flights

Every day

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago in the past 72 hours is $224. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $484.
The fastest flight from Chicago to Jamaica takes 3h 45m
Direct flights go from Chicago to Jamaica every day.
There are 11 airports in Jamaica. From Chicago there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

  • When did momondo last update prices for flights from Chicago to Jamaica?

    Prices for flights from Chicago to Jamaica refresh daily.

  • How many operators does momondo search for flights from Chicago to Jamaica?

  • How old do you have to be to fly from Chicago to Jamaica?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Jamaica.

  • What documentation or ID do you need to fly to Jamaica?

    The necessary travel and health documents for your Jamaica trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Jamaica?

Best airlines flying from Chicago to Jamaica

Compare and see reviews for airlines that fly from Chicago to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $100Free CancellationRating
6.3
8,444 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,180 reviews
Search Delta flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,273 reviews
Search United Airlines flights
American AirlinesPriceFrom $412Free CancellationRating
7.2
11,265 reviews
Search American Airlines flights
SouthwestPriceFrom $518Free CancellationRating
8.0
4,280 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jamaica?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Jamaica. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Jamaica with flexible booking policies on momondo?

Flights from Chicago to Jamaica 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 Jamaica?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Jamaica.

I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Jamaica 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 Jamaica 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.
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