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Cheap flights from Chicago to Jamaica from $100

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 2/8. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
Spirit Airlines Logo
12:57 pm - 7:38 pm
MBJ
-
ORD
7h 41m
1 stop
$368Spirit Airlines
Mon, Jan 26 - Fri, Feb 6
Multiple Airlines Logo
6:36 pm - 10:58 am
ORD
-
MBJ
16h 22m
1 stop
Multiple Airlines Logo
12:00 pm - 7:46 pm
MBJ
-
ORD
7h 46m
1 stop
$369Multiple Airlines
Tue, Mar 17 - Wed, Mar 25
Frontier Logo
5:15 am - 2:23 pm
ORD
-
MBJ
9h 08m
1 stop
Frontier Logo
1:57 pm - 10:39 pm
MBJ
-
ORD
8h 42m
1 stop
$371Frontier
Thu, Apr 2 - Mon, Apr 13
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
Spirit Airlines Logo
12:57 pm - 11:47 pm
MBJ
-
ORD
11h 50m
1 stop
$373Spirit Airlines
Tue, Feb 3 - Sun, Feb 8
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
Spirit Airlines Logo
1:00 pm - 11:47 pm
MBJ
-
ORD
11h 47m
1 stop
$376Spirit Airlines
Sat, Feb 14 - Wed, Feb 18
Delta Logo
6:00 am - 12:53 pm
MDW
-
MBJ
5h 53m
1 stop
Delta Logo
2:19 pm - 10:31 pm
MBJ
-
MDW
9h 12m
1 stop
$384Delta
Sun, Feb 22 - Fri, Feb 27
Frontier Logo
6:48 pm - 9:25 am
MDW
-
MBJ
13h 37m
1 stop
Frontier Logo
10:32 am - 7:59 pm
MBJ
-
MDW
10h 27m
1 stop
$390Frontier
Fri, Feb 20 - Sun, Feb 22
Southwest Logo
7:10 am - 1:55 pm
MDW
-
MBJ
6h 45m
1 stop
Southwest Logo
11:35 am - 3:45 pm
MBJ
-
MDW
4h 10mnonstop
$396Southwest
Mon, Apr 20 - Sat, Apr 25
Southwest Logo
6:45 am - 3:15 pm
MDW
-
MBJ
7h 30m
1 stop
Southwest Logo
1:30 pm - 12:55 am
MBJ
-
MDW
12h 25m
2 stops
$397Southwest
Mon, Feb 23 - Fri, Feb 27
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m
1 stop
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m
1 stop
$409Delta
Sat, Feb 28 - Wed, Mar 4

Delta flights from Chicago to Jamaica

Our best Delta deals on Chicago to Jamaica flight tickets
Delta
Feb 22
MDW6:00 amChicago Midway
5h 53m
1 stop
MBJ12:53 pmMontego Bay Sangster Intl
Feb 27
MBJ2:19 pmMontego Bay Sangster Intl
9h 12m
1 stop
MDW10:31 pmChicago Midway
$384
Delta
Feb 28
ORD6:45 amChicago O'Hare Intl
7h 34m
1 stop
MBJ3:19 pmMontego Bay Sangster Intl
Mar 6
MBJ12:20 pmMontego Bay Sangster Intl
7h 29m
1 stop
ORD6:49 pmChicago O'Hare Intl
$409
Delta
Apr 29
ORD5:20 amChicago O'Hare Intl
7h 56m
1 stop
MBJ1:16 pmMontego Bay Sangster Intl
May 2
MBJ4:55 pmMontego Bay Sangster Intl
14h 40m
2 stops
ORD7:35 amChicago O'Hare Intl
$414

Air Canada flights from Chicago to Jamaica

Our best Air Canada deals on Chicago to Jamaica 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
20h 45m
1 stop
ORD9:00 amChicago O'Hare Intl
$386
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
$394
Air Canada
Jun 16
ORD9:55 amChicago O'Hare Intl
25h 25m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
Jun 21
MBJ12:30 pmMontego Bay Sangster Intl
26h 25m
1 stop
ORD2:55 pmChicago O'Hare Intl
$396

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 January 21, 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

Mon 1/26

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Fri 2/6

12:57 pm-7:38 pm

1 stop7h 41m

$368

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/17

6:36 pm-10:58 am

1 stop16h 22m

Montego Bay Sangster Intl

Wed 3/25

12:00 pm-7:46 pm

1 stop7h 46m

$369

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 4/2

5:15 am-2:23 pm

1 stop9h 08m

Montego Bay Sangster Intl

Mon 4/13

1:57 pm-10:39 pm

1 stop8h 42m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/3

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Sun 2/8

12:57 pm-11:47 pm

1 stop11h 50m

$373

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 2/14

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Wed 2/18

1:00 pm-11:47 pm

1 stop11h 47m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/22

6:00 am-12:53 pm

1 stop5h 53m

Montego Bay Sangster Intl

Fri 2/27

2:19 pm-10:31 pm

1 stop9h 12m

$384

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 2/20

6:48 pm-9:25 am

1 stop13h 37m

Montego Bay Sangster Intl

Sun 2/22

10:32 am-7:59 pm

1 stop10h 27m

$390

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 4/20

7:10 am-1:55 pm

1 stop6h 45m

Montego Bay Sangster Intl

Sat 4/25

11:35 am-3:45 pm

Nonstop4h 10m

$396

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/23

6:45 am-3:15 pm

1 stop7h 30m

Montego Bay Sangster Intl

Fri 2/27

1:30 pm-12:55 am

2 stops12h 25m

$397

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/28

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Wed 3/4

4:44 pm-10:31 pm

1 stop6h 47m

$409

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 $529, 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 $546. 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 $686.

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 week ahead of your departure date. In general, you can expect to find flights to Jamaica for around $579 when searching week 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 $497 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?

No. A direct flight is the cheapest option for a flight between Chicago to Jamaica.

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

$248

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 $248. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $477.
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 $130Free CancellationRating
6.3
8,361 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.7
3,055 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,086 reviews
Search Delta flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,190 reviews
Search United Airlines flights
American AirlinesPriceFrom $422Free CancellationRating
7.2
11,169 reviews
Search American Airlines flights
SouthwestPriceFrom $531Free CancellationRating
8.0
4,266 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

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