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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 9/20. 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

Spirit Airlines Logo
5:59 pm - 12:13 pmORD-KIN
17h 14m1 stop
Spirit Airlines Logo
1:28 pm - 9:00 pmKIN-ORD
8h 32m1 stop
$346Spirit Airlines
Find Deal
Tue, Nov 11 - Wed, Dec 3
Spirit Airlines Logo
6:44 pm - 11:02 amORD-KIN
16h 18m1 stop
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
$359Spirit Airlines
Find Deal
Thu, Sep 11 - Tue, Sep 23
Frontier Logo
6:20 am - 3:15 pmMDW-MBJ
7h 55m1 stop
Frontier Logo
4:53 pm - 11:06 pmMBJ-MDW
7h 13m1 stop
$398Frontier
Find Deal
Fri, Nov 14 - Thu, Nov 20
Frontier Logo
6:20 am - 12:45 pmMDW-MBJ
6h 25m1 stop
Frontier Logo
3:51 pm - 11:25 pmMBJ-MDW
7h 34m1 stop
$399Frontier
Find Deal
Fri, Oct 3 - Fri, Oct 10
American Airlines Logo
9:45 am - 3:01 pmORD-MBJ
4h 16mnonstop
American Airlines Logo
3:14 pm - 6:55 pmMBJ-ORD
4h 41mnonstop
$410American Airlines
Find Deal
Wed, Nov 19 - Wed, Nov 26
American Airlines Logo
8:29 pm - 12:05 pmORD-MBJ
15h 36m2 stops
American Airlines Logo
1:55 pm - 11:48 pmMBJ-ORD
9h 53m2 stops
$414American Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 13
Southwest Logo
7:05 am - 1:55 pmMDW-MBJ
6h 50m1 stop
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
$420Southwest
Find Deal
Mon, Oct 20 - Fri, Oct 24
Southwest Logo
8:45 pm - 2:00 pmMDW-MBJ
17h 15m2 stops
Southwest Logo
12:50 pm - 8:40 pmMBJ-MDW
7h 50m2 stops
$424Southwest
Find Deal
Mon, Oct 20 - Fri, Oct 24
Delta Logo
6:00 am - 4:33 pmMDW-MBJ
9h 33m1 stop
Delta Logo
5:58 pm - 9:51 amMBJ-MDW
16h 53m1 stop
$425Delta
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Sun, Nov 16 - Wed, Nov 26
Delta Logo
7:00 am - 8:25 pmORD-MBJ
12h 25m2 stops
Delta Logo
8:00 am - 6:46 pmMBJ-ORD
11h 46m2 stops
$429Delta
Find Deal
Mon, Feb 16 - Thu, Feb 26

American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets
American Airlines
Nov 19
ORD9:45 amChicago O'Hare Intl
4h 16m
MBJ3:01 pmMontego Bay Sangster Intl
Nov 26
MBJ3:14 pmMontego Bay Sangster Intl
4h 41m
ORD6:55 pmChicago O'Hare Intl
$410
Find similar
American Airlines
Sep 6
ORD8:29 pmChicago O'Hare Intl
15h 36m
2 stops
MBJ12:05 pmMontego Bay Sangster Intl
Sep 13
MBJ1:55 pmMontego Bay Sangster Intl
9h 53m
2 stops
ORD11:48 pmChicago O'Hare Intl
$414
Find similar
American Airlines
Feb 14
ORD8:35 pmChicago O'Hare Intl
17h 04m
1 stop
MBJ2:39 pmMontego Bay Sangster Intl
Feb 19
MBJ2:15 pmMontego Bay Sangster Intl
4h 28m
ORD5:43 pmChicago O'Hare Intl
$415
Find similar

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets
Frontier
Nov 14
MDW6:20 amChicago Midway
7h 55m
1 stop
MBJ3:15 pmMontego Bay Sangster Intl
Nov 20
MBJ4:53 pmMontego Bay Sangster Intl
7h 13m
1 stop
MDW11:06 pmChicago Midway
$398
Find similar
Frontier
Oct 3
MDW6:20 amChicago Midway
6h 25m
1 stop
MBJ12:45 pmMontego Bay Sangster Intl
Oct 10
MBJ3:51 pmMontego Bay Sangster Intl
7h 34m
1 stop
MDW11:25 pmChicago Midway
$399
Find similar
Frontier
Sep 29
MDW6:20 amChicago Midway
6h 25m
1 stop
MBJ12:45 pmMontego Bay Sangster Intl
Oct 4
MBJ2:05 pmMontego Bay Sangster Intl
9h 12m
1 stop
MDW11:17 pmChicago Midway
$402
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 August 21, 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

Tue 11/11

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Wed 12/3

1:28 pm-9:00 pm

1 stop8h 32m

$346

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 9/11

6:44 pm-11:02 am

1 stop16h 18m

Kingston Norman Manley

Tue 9/23

12:08 pm-10:48 pm

1 stop10h 40m

$359

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 11/14

6:20 am-3:15 pm

1 stop7h 55m

Montego Bay Sangster Intl

Thu 11/20

4:53 pm-11:06 pm

1 stop7h 13m

$398

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 10/3

6:20 am-12:45 pm

1 stop6h 25m

Montego Bay Sangster Intl

Fri 10/10

3:51 pm-11:25 pm

1 stop7h 34m

$399

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/19

9:45 am-3:01 pm

Nonstop4h 16m

Montego Bay Sangster Intl

Wed 11/26

3:14 pm-6:55 pm

Nonstop4h 41m

$410

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 9/6

8:29 pm-12:05 pm

2 stops15h 36m

Montego Bay Sangster Intl

Sat 9/13

1:55 pm-11:48 pm

2 stops9h 53m

$414

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/20

7:05 am-1:55 pm

1 stop6h 50m

Montego Bay Sangster Intl

Fri 10/24

12:50 pm-8:40 pm

2 stops7h 50m

$420

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/20

8:45 pm-2:00 pm

2 stops17h 15m

Montego Bay Sangster Intl

Fri 10/24

12:50 pm-8:40 pm

2 stops7h 50m

$424

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 11/16

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

Wed 11/26

5:58 pm-9:51 am

1 stop16h 53m

$425

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/16

7:00 am-8:25 pm

2 stops12h 25m

Montego Bay Sangster Intl

Thu 2/26

8:00 am-6:46 pm

2 stops11h 46m

$429

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 February. Flight prices, which tend to average around $528, 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 February, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $533.

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 Sunday when prices can be found for as low as $534. 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 $677.

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 $603 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 $607 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 $532 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?

You could potentially save up to 19% 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

$194

Fastest flight time

3h 55m

Direct flights

Every day

Airports in Jamaica

1 airport
The best one-way flight to Jamaica from Chicago in the past 72 hours is $194. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $513.
The fastest flight from Chicago to Jamaica takes 3h 55m
Direct flights go from Chicago to Jamaica every day.
There is 1 airport near Jamaica: 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 $266Free CancellationRating
6.3
8,035 reviews
Search Spirit Airlines flights
DeltaPriceFrom $295Free CancellationRating
7.9
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $424Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
American AirlinesPriceFrom $436Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,245 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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