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Cheap flights from Chicago to Jamaica from $163

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 8/25. 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
7:00 am - 1:48 pm
ORD
-
MBJ
6h 48m
1 stop
JetBlue Logo
2:00 pm - 11:44 pm
MBJ
-
ORD
10h 44m
1 stop
$394JetBlue
Sat, Oct 31 - Tue, Nov 10
United Airlines Logo
9:38 pm - 1:30 pm
ORD
-
MBJ
15h 52m
1 stop
United Airlines Logo
12:52 pm - 11:21 pm
MBJ
-
ORD
10h 29m
1 stop
$407United Airlines
Fri, Oct 16 - Mon, Oct 19
Delta Logo
6:40 am - 3:34 pm
ORD
-
MBJ
8h 54m
1 stop
Delta Logo
1:09 pm - 8:55 pm
MBJ
-
ORD
7h 46m
1 stop
$414Delta
Sun, Aug 16 - Sat, Aug 22
Delta Logo
6:40 am - 3:34 pm
ORD
-
MBJ
8h 54m
1 stop
Delta Logo
4:59 pm - 7:56 am
MBJ
-
ORD
14h 57m
2 stops
$419Delta
Sun, Aug 16 - Thu, Aug 20
Southwest Logo
5:00 am - 12:50 pm
MDW
-
MBJ
7h 50m
1 stop
Southwest Logo
2:15 pm - 10:20 pm
MBJ
-
MDW
8h 05m
2 stops
$421Southwest
Sat, Aug 22 - Fri, Aug 28
American Airlines Logo
8:37 am - 4:24 pm
ORD
-
KIN
7h 47m
1 stop
American Airlines Logo
5:24 pm - 12:35 am
KIN
-
ORD
7h 11m
1 stop
$430American Airlines
Mon, Aug 24 - Mon, Aug 31
American Airlines Logo
8:00 am - 4:26 pm
ORD
-
KIN
8h 26m
2 stops
American Airlines Logo
2:00 pm - 11:52 pm
KIN
-
ORD
9h 52m
2 stops
$432American Airlines
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
5:05 am - 2:25 pm
MDW
-
MBJ
8h 20m
1 stop
Southwest Logo
1:00 pm - 7:00 pm
MBJ
-
MDW
7h 00m
1 stop
$459Southwest
Sun, Dec 6 - Wed, Dec 9
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
$472Frontier
Tue, Aug 11 - Sat, Aug 15
Frontier Logo
6:05 am - 12:24 pm
MDW
-
MBJ
6h 19m
1 stop
Frontier Logo
1:32 pm - 10:03 pm
MBJ
-
MDW
8h 31m
1 stop
$482Frontier
Sun, Aug 2 - Thu, Aug 6

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Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets
Southwest
Aug 22
MDW5:00 amChicago Midway
7h 50m
1 stop
MBJ12:50 pmMontego Bay Sangster Intl
Aug 28
MBJ2:15 pmMontego Bay Sangster Intl
8h 05m
2 stops
MDW10:20 pmChicago Midway
$421
Southwest
Sep 19
MDW5:55 amChicago Midway
6h 30m
1 stop
MBJ12:25 pmMontego Bay Sangster Intl
Sep 23
MBJ1:55 pmMontego Bay Sangster Intl
6h 50m
1 stop
MDW8:45 pmChicago Midway
$460
Southwest
Aug 17
MDW5:55 amChicago Midway
7h 20m
2 stops
MBJ1:15 pmMontego Bay Sangster Intl
Aug 20
MBJ2:15 pmMontego Bay Sangster Intl
7h 15m
1 stop
MDW9:30 pmChicago Midway
$463

JetBlue flights from Chicago to Jamaica

Our best JetBlue deals on Chicago to Jamaica flight tickets
JetBlue
Oct 31
ORD7:00 amChicago O'Hare Intl
6h 48m
1 stop
MBJ1:48 pmMontego Bay Sangster Intl
Nov 10
MBJ2:00 pmMontego Bay Sangster Intl
10h 44m
1 stop
ORD11:44 pmChicago O'Hare Intl
$394
JetBlue
Dec 5
ORD7:00 amChicago O'Hare Intl
5h 40m
1 stop
MBJ1:40 pmMontego Bay Sangster Intl
Dec 12
MBJ5:00 pmMontego Bay Sangster Intl
7h 44m
1 stop
ORD11:44 pmChicago O'Hare Intl
$418
JetBlue
Nov 3
ORD7:00 amChicago O'Hare Intl
6h 54m
1 stop
MBJ2:54 pmMontego Bay Sangster Intl
Nov 10
MBJ2:00 pmMontego Bay Sangster Intl
10h 44m
1 stop
ORD11:44 pmChicago O'Hare Intl
$421

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 13, 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

Sat 10/31

7:00 am-1:48 pm

1 stop6h 48m

Montego Bay Sangster Intl

Tue 11/10

2:00 pm-11:44 pm

1 stop10h 44m

$394

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 10/16

9:38 pm-1:30 pm

1 stop15h 52m

Montego Bay Sangster Intl

Mon 10/19

12:52 pm-11:21 pm

1 stop10h 29m

$407

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

6:40 am-3:34 pm

1 stop8h 54m

Montego Bay Sangster Intl

Sat 8/22

1:09 pm-8:55 pm

1 stop7h 46m

$414

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 8/16

6:40 am-3:34 pm

1 stop8h 54m

Montego Bay Sangster Intl

Thu 8/20

4:59 pm-7:56 am

2 stops14h 57m

$419

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/22

5:00 am-12:50 pm

1 stop7h 50m

Montego Bay Sangster Intl

Fri 8/28

2:15 pm-10:20 pm

2 stops8h 05m

$421

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 8/24

8:37 am-4:24 pm

1 stop7h 47m

Kingston Norman Manley

Mon 8/31

5:24 pm-12:35 am

1 stop7h 11m

$430

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 8/26

8:00 am-4:26 pm

2 stops8h 26m

Kingston Norman Manley

Wed 9/2

2:00 pm-11:52 pm

2 stops9h 52m

$432

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 12/6

5:05 am-2:25 pm

1 stop8h 20m

Montego Bay Sangster Intl

Wed 12/9

1:00 pm-7:00 pm

1 stop7h 00m

$459

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 8/11

6:05 am-12:27 pm

1 stop6h 22m

Montego Bay Sangster Intl

Sat 8/15

1:32 pm-10:03 pm

1 stop8h 31m

$472
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/2

6:05 am-12:24 pm

1 stop6h 19m

Montego Bay Sangster Intl

Thu 8/6

1:32 pm-10:03 pm

1 stop8h 31m

$482

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 $488. 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 $616.

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

$268

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 $268. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $603.
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
2,815 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.8
8,464 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.1
3,010 reviews
Search JetBlue flights
United AirlinesPriceFrom $297Free CancellationRating
7.4
9,984 reviews
Search United Airlines flights
American AirlinesPriceFrom $318Free CancellationRating
7.1
11,811 reviews
Search American Airlines flights
SouthwestPriceFrom $467Free CancellationRating
8.0
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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