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Cheap flights from Chicago to Jamaica from $137

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 8/12. 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
5:22 am - 1:05 pm
ORD
-
MBJ
7h 43m
1 stop
American Airlines Logo
2:19 pm - 6:00 pm
MBJ
-
ORD
4h 41mnonstop
$337American Airlines
Mon, Oct 26 - Wed, Nov 4
United Airlines Logo
8:42 am - 1:46 pm
ORD
-
MBJ
4h 04mnonstop
United Airlines Logo
2:48 pm - 6:16 pm
MBJ
-
ORD
4h 28mnonstop
$338United Airlines
Tue, Nov 3 - Wed, Nov 11
Southwest Logo
7:50 am - 11:45 am
MDW
-
MBJ
3h 55mnonstop
Southwest Logo
2:30 pm - 6:35 pm
MBJ
-
MDW
4h 05mnonstop
$338Southwest
Sun, Jun 28 - Sat, Jul 4
American Airlines Logo
5:00 am - 12:42 pm
ORD
-
MBJ
6h 42m
1 stop
American Airlines Logo
3:14 pm - 6:55 pm
MBJ
-
ORD
4h 41mnonstop
$342American Airlines
Tue, Nov 3 - Tue, Nov 10
JetBlue Logo
7:00 am - 5:33 pm
ORD
-
MBJ
10h 33m
1 stop
JetBlue Logo
3:10 pm - 11:44 pm
MBJ
-
ORD
8h 34m
1 stop
$346JetBlue
Tue, Sep 8 - Sat, Sep 12
Southwest Logo
5:55 am - 12:25 pm
MDW
-
MBJ
6h 30m
1 stop
Southwest Logo
12:45 pm - 9:00 pm
MBJ
-
MDW
8h 15m
1 stop
$440Southwest
Sat, Aug 22 - Fri, Aug 28
Delta Logo
6:00 am - 1:20 pm
MDW
-
MBJ
7h 20m
1 stop
Delta Logo
5:59 pm - 12:33 pm
MBJ
-
MDW
19h 34m
2 stops
$443Delta
Sun, Oct 25 - Mon, Nov 2
Delta Logo
6:05 am - 1:01 pm
MDW
-
MBJ
6h 56m
1 stop
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
$452Delta
Sun, Aug 16 - Thu, Aug 20
Frontier Logo
6:00 am - 12:27 pm
MDW
-
MBJ
6h 27m
1 stop
Frontier Logo
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
$460Frontier
Mon, Aug 10 - Thu, Aug 13
Frontier Logo
6:00 am - 12:21 pm
MDW
-
MBJ
6h 21m
1 stop
Frontier Logo
1:32 pm - 10:08 pm
MBJ
-
MDW
8h 36m
1 stop
$465Frontier
Sat, Jul 4 - Thu, Jul 9

Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets
Southwest
Jun 28
MDW7:50 amChicago Midway
3h 55m
MBJ11:45 amMontego Bay Sangster Intl
Jul 4
MBJ2:30 pmMontego Bay Sangster Intl
4h 05m
MDW6:35 pmChicago Midway
$338
Southwest
Aug 22
MDW5:55 amChicago Midway
6h 30m
1 stop
MBJ12:25 pmMontego Bay Sangster Intl
Aug 28
MBJ12:45 pmMontego Bay Sangster Intl
8h 15m
1 stop
MDW9:00 pmChicago Midway
$440
Southwest
Jun 28
MDW8:05 amChicago Midway
6h 30m
1 stop
MBJ2:35 pmMontego Bay Sangster Intl
Jul 4
MBJ2:30 pmMontego Bay Sangster Intl
4h 05m
MDW6:35 pmChicago Midway
$447

JetBlue flights from Chicago to Jamaica

Our best JetBlue deals on Chicago to Jamaica flight tickets
JetBlue
Sep 8
ORD7:00 amChicago O'Hare Intl
10h 33m
1 stop
MBJ5:33 pmMontego Bay Sangster Intl
Sep 12
MBJ3:10 pmMontego Bay Sangster Intl
8h 34m
1 stop
ORD11:44 pmChicago O'Hare Intl
$346
JetBlue
Aug 18
ORD7:00 amChicago O'Hare Intl
10h 33m
1 stop
MBJ5:33 pmMontego Bay Sangster Intl
Aug 27
MBJ12:55 pmMontego Bay Sangster Intl
10h 49m
1 stop
ORD11:44 pmChicago O'Hare Intl
$351
JetBlue
Aug 19
ORD7:00 amChicago O'Hare Intl
10h 33m
1 stop
MBJ5:33 pmMontego Bay Sangster Intl
Aug 26
MBJ12:55 pmMontego Bay Sangster Intl
10h 49m
1 stop
ORD11:44 pmChicago O'Hare Intl
$360

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 May 19, 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

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 10/26

5:22 am-1:05 pm

1 stop7h 43m

Montego Bay Sangster Intl

Wed 11/4

2:19 pm-6:00 pm

Nonstop4h 41m

$337

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 11/3

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Wed 11/11

2:48 pm-6:16 pm

Nonstop4h 28m

$338
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 6/28

7:50 am-11:45 am

Nonstop3h 55m

Montego Bay Sangster Intl

Sat 7/4

2:30 pm-6:35 pm

Nonstop4h 05m

$338

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 11/3

5:00 am-12:42 pm

1 stop6h 42m

Montego Bay Sangster Intl

Tue 11/10

3:14 pm-6:55 pm

Nonstop4h 41m

$342

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 9/8

7:00 am-5:33 pm

1 stop10h 33m

Montego Bay Sangster Intl

Sat 9/12

3:10 pm-11:44 pm

1 stop8h 34m

$346

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/22

5:55 am-12:25 pm

1 stop6h 30m

Montego Bay Sangster Intl

Fri 8/28

12:45 pm-9:00 pm

1 stop8h 15m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 10/25

6:00 am-1:20 pm

1 stop7h 20m

Montego Bay Sangster Intl

Mon 11/2

5:59 pm-12:33 pm

2 stops19h 34m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

6:05 am-1:01 pm

1 stop6h 56m

Montego Bay Sangster Intl

Thu 8/20

1:09 pm-10:36 pm

1 stop9h 27m

$452

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 8/10

6:00 am-12:27 pm

1 stop6h 27m

Montego Bay Sangster Intl

Thu 8/13

1:32 pm-10:08 pm

1 stop8h 36m

$460

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 7/4

6:00 am-12:21 pm

1 stop6h 21m

Montego Bay Sangster Intl

Thu 7/9

1:32 pm-10:08 pm

1 stop8h 36m

$465

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 $492. 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 $636.

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 $530 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 $471 on momondo.

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

There are 2 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 21% 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

$138

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 $138. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $403.
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

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
Spirit AirlinesPriceFrom $100Free CancellationRating
6.2
8,612 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.6
2,944 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,454 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.2
2,983 reviews
Search JetBlue flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,736 reviews
Search United Airlines flights
American AirlinesPriceFrom $319Free CancellationRating
7.1
11,641 reviews
Search American Airlines flights
SouthwestPriceFrom $468Free CancellationRating
7.9
4,285 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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