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Cheap flights from Chicago to Jamaica from $118

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 4/5. 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.
American Airlines Logo
8:53 pm - 3:20 pm
ORD
-
MBJ
18h 27m
1 stop
American Airlines Logo
2:00 pm - 6:30 pm
MBJ
-
ORD
4h 30mnonstop
$294American Airlines
Sat, Aug 1 - Thu, Aug 6
American Airlines Logo
6:05 am - 1:25 pm
ORD
-
MBJ
7h 20m
1 stop
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
$297American Airlines
Sun, Apr 12 - Sun, Apr 19
United Airlines Logo
8:42 am - 12:46 pm
ORD
-
MBJ
4h 04mnonstop
United Airlines Logo
1:48 pm - 6:13 pm
MBJ
-
ORD
4h 25mnonstop
$298United Airlines
Wed, Mar 11 - Wed, Mar 18
American Airlines Logo
8:46 pm - 9:13 am
ORD
-
MBJ
12h 27m
1 stop
American Airlines Logo
2:29 pm - 4:21 pm
MBJ
-
ORD
25h 52m
1 stop
$299American Airlines
Sat, May 9 - Fri, May 15
American Airlines Logo
5:28 pm - 9:07 am
ORD
-
MBJ
15h 39m
1 stop
American Airlines Logo
10:07 am - 8:53 am
MBJ
-
ORD
22h 46m
1 stop
$300American Airlines
Mon, Mar 23 - Thu, Mar 26
Spirit Airlines Logo
5:05 am - 11:05 am
ORD
-
MBJ
6h 00m
1 stop
Spirit Airlines Logo
12:00 pm - 8:03 am
MBJ
-
ORD
20h 03m
2 stops
$305Spirit Airlines
Mon, Apr 13 - Wed, Apr 22
Southwest Logo
7:00 am - 1:55 pm
MDW
-
MBJ
6h 55m
1 stop
Southwest Logo
2:25 pm - 9:25 pm
MBJ
-
MDW
7h 00m
1 stop
$343Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
7:00 am - 1:55 pm
MDW
-
MBJ
6h 55m
1 stop
Southwest Logo
12:15 pm - 7:10 am
MBJ
-
MDW
18h 55m
2 stops
$348Southwest
Wed, Apr 29 - Wed, May 6
Delta Logo
12:52 pm - 8:00 pm
MDW
-
KIN
7h 08m
1 stop
Delta Logo
9:00 am - 4:26 pm
KIN
-
MDW
7h 26m
1 stop
$496Delta
Thu, Apr 16 - Mon, Apr 20
Delta Logo
12:47 pm - 8:00 pm
MDW
-
KIN
7h 13m
1 stop
Delta Logo
9:00 am - 10:28 pm
KIN
-
MDW
13h 28m
1 stop
$566Delta
Fri, Apr 10 - Fri, Apr 17

American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets
American Airlines
Aug 1
ORD8:53 pmChicago O'Hare Intl
18h 27m
1 stop
MBJ3:20 pmMontego Bay Sangster Intl
Aug 6
MBJ2:00 pmMontego Bay Sangster Intl
4h 30m
ORD6:30 pmChicago O'Hare Intl
$294
American Airlines
Apr 15
ORD7:15 amChicago O'Hare Intl
6h 10m
1 stop
MBJ1:25 pmMontego Bay Sangster Intl
Apr 19
MBJ1:15 pmMontego Bay Sangster Intl
4h 40m
ORD5:55 pmChicago O'Hare Intl
$297
American Airlines
May 9
ORD8:46 pmChicago O'Hare Intl
12h 27m
1 stop
MBJ9:13 amMontego Bay Sangster Intl
May 15
MBJ2:29 pmMontego Bay Sangster Intl
25h 52m
1 stop
ORD4:21 pmChicago O'Hare Intl
$299

United Airlines flights from Chicago to Jamaica

Our best United Airlines deals on Chicago to Jamaica flight tickets
United Airlines
Mar 11
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ12:46 pmMontego Bay Sangster Intl
Mar 18
MBJ1:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$298
United Airlines
Apr 5
ORD8:40 amChicago O'Hare Intl
4h 10m
MBJ12:50 pmMontego Bay Sangster Intl
Apr 9
MBJ1:52 pmMontego Bay Sangster Intl
4h 23m
ORD6:15 pmChicago O'Hare Intl
$317
United Airlines
Mar 11
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ12:46 pmMontego Bay Sangster Intl
Mar 17
MBJ1:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$318

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 26, 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

Sat 8/1

8:53 pm-3:20 pm

1 stop18h 27m

Montego Bay Sangster Intl

Thu 8/6

2:00 pm-6:30 pm

Nonstop4h 30m

$294

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/12

6:05 am-1:25 pm

1 stop7h 20m

Montego Bay Sangster Intl

Sun 4/19

1:15 pm-5:55 pm

Nonstop4h 40m

$297

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/11

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Wed 3/18

1:48 pm-6:13 pm

Nonstop4h 25m

$298

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 5/9

8:46 pm-9:13 am

1 stop12h 27m

Montego Bay Sangster Intl

Fri 5/15

2:29 pm-4:21 pm

1 stop25h 52m

$299

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 3/23

5:28 pm-9:07 am

1 stop15h 39m

Montego Bay Sangster Intl

Thu 3/26

10:07 am-8:53 am

1 stop22h 46m

$300

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 4/13

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

Wed 4/22

12:00 pm-8:03 am

2 stops20h 03m

$305

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/29

7:00 am-1:55 pm

1 stop6h 55m

Montego Bay Sangster Intl

Wed 5/6

2:25 pm-9:25 pm

1 stop7h 00m

$343

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 4/29

7:00 am-1:55 pm

1 stop6h 55m

Montego Bay Sangster Intl

Wed 5/6

12:15 pm-7:10 am

2 stops18h 55m

$348

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 4/16

12:52 pm-8:00 pm

1 stop7h 08m

Kingston Norman Manley

Mon 4/20

9:00 am-4:26 pm

1 stop7h 26m

$496

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 4/10

12:47 pm-8:00 pm

1 stop7h 13m

Kingston Norman Manley

Fri 4/17

9:00 am-10:28 pm

1 stop13h 28m

$566

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 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 Jamaica?

The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $529. 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 $664.

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 16% 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

$180

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 $180. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $464.
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
8,494 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.7
3,040 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,237 reviews
Search Delta flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,347 reviews
Search United Airlines flights
American AirlinesPriceFrom $404Free CancellationRating
7.2
11,352 reviews
Search American Airlines flights
SouthwestPriceFrom $518Free CancellationRating
8.0
4,299 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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