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Cheap flights from Chicago to Jamaica from $154

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 9/13. 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.

Find the cheapest flights from Chicago to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
6:00 am - 12:09 pm
ORD
-
KIN
6h 09m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
KIN
-
ORD
8h 26m
1 stop
$390JetBlue
Tue, Sep 22 - Wed, Sep 23
JetBlue Logo
7:00 am - 1:48 pm
ORD
-
MBJ
6h 48m
1 stop
JetBlue Logo
3:59 pm - 11:44 pm
MBJ
-
ORD
8h 45m
1 stop
$391JetBlue
Fri, Oct 30 - Tue, Nov 3
American Airlines Logo
7:47 am - 4:02 pm
ORD
-
KIN
8h 15m
2 stops
American Airlines Logo
5:03 pm - 12:38 am
KIN
-
ORD
7h 35m
1 stop
$391American Airlines
Sat, Oct 3 - Sat, Oct 10
American Airlines Logo
6:59 am - 4:02 pm
ORD
-
KIN
9h 03m
1 stop
American Airlines Logo
1:08 pm - 11:32 pm
KIN
-
ORD
10h 24m
1 stop
$398American Airlines
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
5:05 am - 2:25 pm
MDW
-
MBJ
8h 20m
1 stop
Southwest Logo
1:00 pm - 9:20 pm
MBJ
-
MDW
9h 20m
1 stop
$459Southwest
Sun, Dec 6 - Thu, Dec 10
Southwest Logo
8:40 pm - 2:25 pm
MDW
-
MBJ
16h 45m
2 stops
Southwest Logo
1:00 pm - 9:20 pm
MBJ
-
MDW
9h 20m
1 stop
$464Southwest
Sun, Dec 6 - Thu, Dec 10
Delta Logo
12:46 pm - 8:13 pm
MDW
-
KIN
7h 27m
1 stop
Delta Logo
9:13 am - 10:36 pm
KIN
-
MDW
13h 23m
1 stop
$464Delta
Fri, Aug 21 - Fri, Aug 28
Delta Logo
6:42 pm - 8:13 pm
MDW
-
KIN
25h 31m
2 stops
Delta Logo
9:13 am - 9:17 am
KIN
-
MDW
24h 04m
2 stops
$469Delta
Fri, Aug 21 - Fri, Aug 28
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:39 pm - 10:03 pm
MBJ
-
MDW
8h 24m
1 stop
$472Frontier
Wed, Jul 29 - Sun, Aug 16
Frontier Logo
6:40 am - 1:31 pm
MDW
-
MBJ
6h 51m
1 stop
Frontier Logo
2:49 pm - 9:58 pm
MBJ
-
MDW
7h 09m
1 stop
$485Frontier
Mon, Oct 12 - Mon, Oct 26

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Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets
Frontier
Jul 29
MDW6:05 amChicago Midway
6h 22m
1 stop
MBJ12:27 pmMontego Bay Sangster Intl
Aug 16
MBJ1:39 pmMontego Bay Sangster Intl
8h 24m
1 stop
MDW10:03 pmChicago Midway
$472
Frontier
Oct 12
MDW6:40 amChicago Midway
6h 51m
1 stop
MBJ1:31 pmMontego Bay Sangster Intl
Oct 26
MBJ2:49 pmMontego Bay Sangster Intl
7h 09m
1 stop
MDW9:58 pmChicago Midway
$485
Frontier
Oct 3
MDW7:25 amChicago Midway
6h 06m
1 stop
MBJ1:31 pmMontego Bay Sangster Intl
Oct 10
MBJ2:46 pmMontego Bay Sangster Intl
7h 12m
1 stop
MDW9:58 pmChicago Midway
$486

JetBlue flights from Chicago to Jamaica

Our best JetBlue deals on Chicago to Jamaica flight tickets
JetBlue
Sep 22
ORD6:00 amChicago O'Hare Intl
6h 09m
1 stop
KIN12:09 pmKingston Norman Manley
Sep 23
KIN3:05 pmKingston Norman Manley
8h 26m
1 stop
ORD11:31 pmChicago O'Hare Intl
$390
JetBlue
Oct 30
ORD7:00 amChicago O'Hare Intl
6h 48m
1 stop
MBJ1:48 pmMontego Bay Sangster Intl
Nov 3
MBJ3:59 pmMontego Bay Sangster Intl
8h 45m
1 stop
ORD11:44 pmChicago O'Hare Intl
$391
JetBlue
Nov 2
ORD7:00 amChicago O'Hare Intl
6h 54m
1 stop
MBJ2:54 pmMontego Bay Sangster Intl
Nov 11
MBJ3:59 pmMontego Bay Sangster Intl
8h 45m
1 stop
ORD11:44 pmChicago O'Hare Intl
$394

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 July 8, 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

Cheapest round-trip

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 9/22

6:00 am-12:09 pm

1 stop6h 09m

Kingston Norman Manley

Wed 9/23

3:05 pm-11:31 pm

1 stop8h 26m

$390

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/30

7:00 am-1:48 pm

1 stop6h 48m

Montego Bay Sangster Intl

Tue 11/3

3:59 pm-11:44 pm

1 stop8h 45m

$391

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 10/3

7:47 am-4:02 pm

2 stops8h 15m

Kingston Norman Manley

Sat 10/10

5:03 pm-12:38 am

1 stop7h 35m

$391

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Fri 9/11

6:59 am-4:02 pm

1 stop9h 03m

Kingston Norman Manley

Mon 9/14

1:08 pm-11:32 pm

1 stop10h 24m

$398

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 12/6

5:05 am-2:25 pm

1 stop8h 20m

Montego Bay Sangster Intl

Thu 12/10

1:00 pm-9:20 pm

1 stop9h 20m

$459

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 12/6

8:40 pm-2:25 pm

2 stops16h 45m

Montego Bay Sangster Intl

Thu 12/10

1:00 pm-9:20 pm

1 stop9h 20m

$464

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 8/21

12:46 pm-8:13 pm

1 stop7h 27m

Kingston Norman Manley

Fri 8/28

9:13 am-10:36 pm

1 stop13h 23m

$464

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 8/21

6:42 pm-8:13 pm

2 stops25h 31m

Kingston Norman Manley

Fri 8/28

9:13 am-9:17 am

2 stops24h 04m

$469

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 7/29

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Sun 8/16

1:39 pm-10:03 pm

1 stop8h 24m

$472
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/12

6:40 am-1:31 pm

1 stop6h 51m

Montego Bay Sangster Intl

Mon 10/26

2:49 pm-9:58 pm

1 stop7h 09m

$485

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 December. Flight prices, which tend to average around $84, 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 December, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $93.

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 $491. 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 $619.

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 from Chicago 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 $527 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 $468 on momondo.

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

There are 4 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

$284

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago in the past 72 hours is $284. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $597.
The fastest flight from Chicago to Jamaica takes 3h 55m
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

Frequently asked questions about flying from Chicago to Jamaica

  • 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
FrontierPriceFrom $144Free CancellationRating
5.6
2,835 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.8
8,450 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.1
3,013 reviews
Search JetBlue flights
United AirlinesPriceFrom $297Free CancellationRating
7.4
9,949 reviews
Search United Airlines flights
American AirlinesPriceFrom $318Free CancellationRating
7.1
11,783 reviews
Search American Airlines flights
SouthwestPriceFrom $467Free CancellationRating
7.9
4,249 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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