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Cheap flights from Chicago to Jamaica from $104

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 2/3. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:15 am - 12:12 pm
ORD
-
KIN
5h 57m1 stop
Spirit Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m1 stop
$333Spirit Airlines
Mon, Jan 26 - Fri, Jan 30
Spirit Airlines Logo
5:15 am - 12:12 pm
ORD
-
KIN
5h 57m1 stop
Spirit Airlines Logo
1:17 pm - 11:47 pm
KIN
-
ORD
11h 30m1 stop
$337Spirit Airlines
Mon, Feb 9 - Thu, Feb 19
Spirit Airlines Logo
4:43 pm - 12:15 pm
ORD
-
KIN
18h 32m1 stop
Spirit Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m1 stop
$351Spirit Airlines
Wed, Feb 18 - Sun, Feb 22
American Airlines Logo
10:09 am - 3:22 pm
ORD
-
MBJ
4h 13mnonstop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$377American Airlines
Mon, Jan 12 - Thu, Jan 15
American Airlines Logo
5:26 pm - 12:24 pm
ORD
-
MBJ
17h 58m1 stop
American Airlines Logo
3:12 pm - 6:51 pm
MBJ
-
ORD
4h 39mnonstop
$381American Airlines
Sat, Jan 24 - Thu, Jan 29
Delta Logo
6:45 am - 3:20 pm
MDW
-
MBJ
7h 35m1 stop
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
$435Delta
Sun, Jan 18 - Wed, Jan 21
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m1 stop
Delta Logo
4:44 pm - 12:46 pm
MBJ
-
MDW
21h 02m2 stops
$440Delta
Fri, Feb 27 - Thu, Mar 5
Frontier Logo
9:04 pm - 9:00 am
MDW
-
MBJ
10h 56m1 stop
Frontier Logo
10:40 am - 9:33 pm
MBJ
-
MDW
11h 53m1 stop
$443Frontier
Sun, Feb 15 - Sat, Feb 21
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 9:00 pm
MBJ
-
MDW
8h 00m1 stop
$463Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m1 stop
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m2 stops
$468Southwest
Wed, Feb 18 - Wed, Feb 25

American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets
American Airlines
Jan 12
ORD10:09 amChicago O'Hare Intl
4h 13m
MBJ3:22 pmMontego Bay Sangster Intl
Jan 15
MBJ3:12 pmMontego Bay Sangster Intl
4h 39m
ORD6:51 pmChicago O'Hare Intl
$377
Find similar
American Airlines
Jan 24
ORD5:26 pmChicago O'Hare Intl
17h 58m
1 stop
MBJ12:24 pmMontego Bay Sangster Intl
Jan 29
MBJ3:12 pmMontego Bay Sangster Intl
4h 39m
ORD6:51 pmChicago O'Hare Intl
$381
Find similar
American Airlines
Jan 18
ORD10:09 amChicago O'Hare Intl
4h 13m
MBJ3:22 pmMontego Bay Sangster Intl
Jan 21
MBJ4:16 pmMontego Bay Sangster Intl
7h 52m
1 stop
ORD11:08 pmChicago O'Hare Intl
$387
Find similar

Air Canada flights from Chicago to Jamaica

Our best Air Canada deals on Chicago to Jamaica flight tickets
Air Canada
Jun 6
ORD6:20 pmChicago O'Hare Intl
17h 00m
2 stops
MBJ11:20 amMontego Bay Sangster Intl
Jun 10
MBJ12:15 pmMontego Bay Sangster Intl
20h 45m
1 stop
ORD9:00 amChicago O'Hare Intl
$392
Find similar
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
31h 53m
2 stops
ORD8:08 pmChicago O'Hare Intl
$395
Find similar
Air Canada
Jan 8
ORD12:50 pmChicago O'Hare Intl
28h 15m
1 stop
MBJ6:05 pmMontego Bay Sangster Intl
Jan 11
MBJ7:05 pmMontego Bay Sangster Intl
24h 46m
1 stop
ORD6:51 pmChicago O'Hare Intl
$412
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 December 23, 2025.
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

Mon 1/26

5:15 am-12:12 pm

1 stop5h 57m

Kingston Norman Manley

Fri 1/30

1:17 pm-11:22 am

1 stop23h 05m

$333

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 2/9

5:15 am-12:12 pm

1 stop5h 57m

Kingston Norman Manley

Thu 2/19

1:17 pm-11:47 pm

1 stop11h 30m

$337

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 2/18

4:43 pm-12:15 pm

1 stop18h 32m

Kingston Norman Manley

Sun 2/22

1:17 pm-11:22 am

1 stop23h 05m

$351

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/12

10:09 am-3:22 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Thu 1/15

3:12 pm-6:51 pm

Nonstop4h 39m

$377

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 1/24

5:26 pm-12:24 pm

1 stop17h 58m

Montego Bay Sangster Intl

Thu 1/29

3:12 pm-6:51 pm

Nonstop4h 39m

$381

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 1/18

6:45 am-3:20 pm

1 stop7h 35m

Montego Bay Sangster Intl

Wed 1/21

4:45 pm-10:22 pm

1 stop6h 37m

$435

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 2/27

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Thu 3/5

4:44 pm-12:46 pm

2 stops21h 02m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 2/15

9:04 pm-9:00 am

1 stop10h 56m

Montego Bay Sangster Intl

Sat 2/21

10:40 am-9:33 pm

1 stop11h 53m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/25

2:00 pm-9:00 pm

1 stop8h 00m

$463

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Wed 2/25

2:00 pm-10:05 pm

2 stops9h 05m

$468

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 $544. 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 time of day to depart on your flight to Jamaica?

Our most recent data shows that the best time of day to fly to Jamaica is at noon. Flights from Chicago to Jamaica during this time can be as low as $287. In the morning is when there is more demand to fly to Jamaica, so prices are often more expensive at around $602 per ticket.

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 $581 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 $546 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

$215

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 $215. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $459.
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 $174Free CancellationRating
6.3
8,194 reviews
Search Spirit Airlines flights
DeltaPriceFrom $186Free CancellationRating
7.9
8,014 reviews
Search Delta flights
FrontierPriceFrom $341Free CancellationRating
5.8
3,074 reviews
Search Frontier flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights
American AirlinesPriceFrom $430Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,253 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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