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Cheap flights from Chicago to Jamaica from $98

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 2/10. 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
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
5:32 pm - 12:12 pm
ORD
-
KIN
17h 40m1 stop
Spirit Airlines Logo
1:17 pm - 11:47 pm
KIN
-
ORD
11h 30m1 stop
$344Spirit Airlines
Thu, Jan 29 - Mon, Feb 2
Multiple Airlines Logo
3:40 pm - 12:15 pm
ORD
-
KIN
19h 35m1 stop
Multiple Airlines Logo
1:17 pm - 11:24 pm
KIN
-
ORD
11h 07m1 stop
$348Multiple Airlines
Sun, Feb 15 - Thu, Feb 19
Multiple Airlines Logo
3:40 pm - 12:15 pm
ORD
-
KIN
19h 35m1 stop
Multiple Airlines Logo
1:17 pm - 9:13 pm
KIN
-
ORD
8h 56m1 stop
$356Multiple Airlines
Sun, Feb 15 - Mon, Feb 23
Spirit Airlines Logo
5:32 pm - 12:12 pm
ORD
-
KIN
17h 40m1 stop
Spirit Airlines Logo
1:17 pm - 7:38 pm
KIN
-
ORD
7h 21m1 stop
$359Spirit Airlines
Sat, Jan 31 - Fri, Feb 6
Frontier Logo
4:42 pm - 8:50 am
ORD
-
MBJ
15h 08m1 stop
Frontier Logo
10:40 am - 10:39 pm
MBJ
-
ORD
12h 59m1 stop
$386Frontier
Thu, Feb 12 - Sat, Feb 21
Frontier Logo
12:22 pm - 8:50 am
MDW
-
MBJ
19h 28m1 stop
Frontier Logo
10:32 am - 7:59 pm
MBJ
-
MDW
10h 27m1 stop
$394Frontier
Thu, Feb 19 - Sun, Feb 22
Southwest Logo
3:25 pm - 1:00 pm
MDW
-
MBJ
20h 35m2 stops
Southwest Logo
1:30 pm - 9:10 pm
MBJ
-
MDW
8h 40m1 stop
$421Southwest
Sun, Feb 1 - Thu, Feb 5
Delta Logo
6:14 pm - 11:13 am
MDW
-
MBJ
15h 59m1 stop
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m1 stop
$427Delta
Mon, Feb 9 - Wed, Feb 18
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
Delta Logo
2:19 pm - 10:33 pm
MBJ
-
MDW
9h 14m1 stop
$436Delta
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
5:30 am - 1:00 pm
MDW
-
MBJ
6h 30m1 stop
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m2 stops
$454Southwest
Mon, Feb 9 - Wed, Feb 18

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
19h 50m
2 stops
ORD8:05 amChicago O'Hare Intl
$384
Find similar
Air Canada
Jun 7
ORD8:20 pmChicago O'Hare Intl
15h 00m
1 stop
MBJ11:20 amMontego Bay Sangster Intl
Jun 11
MBJ12:15 pmMontego Bay Sangster Intl
20h 45m
1 stop
ORD9:00 amChicago O'Hare Intl
$386
Find similar
Air Canada
Jun 4
ORD10:53 amChicago O'Hare Intl
24h 27m
2 stops
MBJ11:20 amMontego Bay Sangster Intl
Jun 7
MBJ12:15 pmMontego Bay Sangster Intl
20h 45m
1 stop
ORD9:00 amChicago O'Hare Intl
$396
Find similar

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets
Frontier
Feb 19
MDW12:22 pmChicago Midway
19h 28m
1 stop
MBJ8:50 amMontego Bay Sangster Intl
Feb 22
MBJ10:32 amMontego Bay Sangster Intl
10h 27m
1 stop
MDW7:59 pmChicago Midway
$394
Find similar
Frontier
Apr 2
ORD5:05 amChicago O'Hare Intl
9h 41m
1 stop
MBJ2:46 pmMontego Bay Sangster Intl
Apr 13
MBJ4:06 pmMontego Bay Sangster Intl
7h 55m
1 stop
ORD12:01 amChicago O'Hare Intl
$411
Find similar
Frontier
Feb 12
MDW6:25 amChicago Midway
6h 28m
1 stop
MBJ1:53 pmMontego Bay Sangster Intl
Feb 16
MBJ10:05 amMontego Bay Sangster Intl
10h 42m
1 stop
MDW7:47 pmChicago Midway
$413
Find similar

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 6, 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

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 1/29

5:32 pm-12:12 pm

1 stop17h 40m

Kingston Norman Manley

Mon 2/2

1:17 pm-11:47 pm

1 stop11h 30m

$344

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 2/15

3:40 pm-12:15 pm

1 stop19h 35m

Kingston Norman Manley

Thu 2/19

1:17 pm-11:24 pm

1 stop11h 07m

$348

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 2/15

3:40 pm-12:15 pm

1 stop19h 35m

Kingston Norman Manley

Mon 2/23

1:17 pm-9:13 pm

1 stop8h 56m

$356

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 1/31

5:32 pm-12:12 pm

1 stop17h 40m

Kingston Norman Manley

Fri 2/6

1:17 pm-7:38 pm

1 stop7h 21m

$359

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 2/12

4:42 pm-8:50 am

1 stop15h 08m

Montego Bay Sangster Intl

Sat 2/21

10:40 am-10:39 pm

1 stop12h 59m

$386

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 2/19

12:22 pm-8:50 am

1 stop19h 28m

Montego Bay Sangster Intl

Sun 2/22

10:32 am-7:59 pm

1 stop10h 27m

$394

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/1

3:25 pm-1:00 pm

2 stops20h 35m

Montego Bay Sangster Intl

Thu 2/5

1:30 pm-9:10 pm

1 stop8h 40m

$421

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/9

6:14 pm-11:13 am

1 stop15h 59m

Montego Bay Sangster Intl

Wed 2/18

4:44 pm-10:31 pm

1 stop6h 47m

$427

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/17

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Tue 2/24

2:19 pm-10:33 pm

1 stop9h 14m

$436

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/9

5:30 am-1:00 pm

1 stop6h 30m

Montego Bay Sangster Intl

Wed 2/18

2:00 pm-10:05 pm

2 stops9h 05m

$454

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 $532, 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 $547. 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 $684.

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 $580 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

$242

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago in the past 72 hours is $242. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $432.
The fastest flight from Chicago to Jamaica takes 3h 50m
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 $168Free CancellationRating
6.3
8,273 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
8,017 reviews
Search Delta flights
FrontierPriceFrom $341Free CancellationRating
5.7
3,064 reviews
Search Frontier flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,132 reviews
Search United Airlines flights
American AirlinesPriceFrom $429Free CancellationRating
7.2
11,082 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,247 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.
Start using Trips
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Find better results for your trip to Jamaica

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