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Cheap flights from Chicago O'Hare Intl Airport to Jamaica from $99

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 O'Hare Intl Airport to Jamaica departing on 10/7. 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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Find the cheapest flights from Chicago O'Hare Intl Airport 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
$342Spirit Airlines
Find Deal
Tue, Nov 11 - Wed, Dec 3
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
$349Spirit Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
$376United Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
8:44 am - 12:45 pmORD-MBJ
4h 01mnonstop
American Airlines Logo
2:05 pm - 7:25 amMBJ-ORD
17h 20m1 stop
$380American Airlines
Find Deal
Tue, Oct 14 - Sat, Oct 18
United Airlines Logo
8:48 am - 4:12 pmORD-MBJ
6h 24m1 stop
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
$381United Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Multiple Airlines Logo
5:05 am - 2:22 pmORD-MBJ
8h 17m1 stop
Multiple Airlines Logo
1:12 pm - 9:00 pmMBJ-ORD
8h 48m1 stop
$383Multiple Airlines
Find Deal
Sat, Feb 7 - Tue, Feb 10
Multiple Airlines Logo
5:05 am - 11:00 amORD-MBJ
5h 55m1 stop
Multiple Airlines Logo
3:51 pm - 1:06 amMBJ-ORD
33h 15m2 stops
$384Multiple Airlines
Find Deal
Sun, Oct 5 - Thu, Oct 9
American Airlines Logo
5:20 am - 1:05 pmORD-MBJ
7h 45m1 stop
American Airlines Logo
2:05 pm - 7:25 amMBJ-ORD
17h 20m1 stop
$385American Airlines
Find Deal
Wed, Oct 15 - Sat, Oct 18
Delta Logo
9:46 am - 4:34 pmORD-MBJ
5h 48m1 stop
Delta Logo
5:59 pm - 12:02 amMBJ-ORD
7h 03m1 stop
$391Delta
Find Deal
Mon, Nov 17 - Wed, Nov 26
Delta Logo
9:42 am - 3:34 pmORD-MBJ
5h 52m1 stop
Delta Logo
1:48 pm - 7:50 amMBJ-ORD
19h 02m2 stops
$399Delta
Find Deal
Sun, Oct 26 - Wed, Nov 5

United Airlines flights from Chicago O'Hare Intl Airport to Jamaica

Our best United Airlines deals on Chicago O'Hare Intl Airport to Jamaica flight tickets
United Airlines
Nov 8
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Nov 15
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$376
Find similar
United Airlines
Nov 8
ORD8:48 amChicago O'Hare Intl
6h 24m
1 stop
MBJ4:12 pmMontego Bay Sangster Intl
Nov 15
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$381
Find similar
United Airlines
Feb 17
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Feb 25
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$390
Find similar

Delta flights from Chicago O'Hare Intl Airport to Jamaica

Our best Delta deals on Chicago O'Hare Intl Airport to Jamaica flight tickets
Delta
Nov 17
ORD9:46 amChicago O'Hare Intl
5h 48m
1 stop
MBJ4:34 pmMontego Bay Sangster Intl
Nov 26
MBJ5:59 pmMontego Bay Sangster Intl
7h 03m
1 stop
ORD12:02 amChicago O'Hare Intl
$391
Find similar
Delta
Oct 26
ORD9:42 amChicago O'Hare Intl
5h 52m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
Nov 5
MBJ1:48 pmMontego Bay Sangster Intl
19h 02m
2 stops
ORD7:50 amChicago O'Hare Intl
$399
Find similar
Delta
Feb 22
ORD7:10 amChicago O'Hare Intl
12h 15m
1 stop
MBJ8:25 pmMontego Bay Sangster Intl
Feb 27
MBJ4:40 pmMontego Bay Sangster Intl
8h 14m
1 stop
ORD11:54 pmChicago O'Hare Intl
$405
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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

$342

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 11/8

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

Sat 11/15

1:28 pm-9:00 pm

1 stop8h 32m

$349

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/8

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 11/15

2:48 pm-6:13 pm

Nonstop4h 25m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 10/14

8:44 am-12:45 pm

Nonstop4h 01m

Montego Bay Sangster Intl

Sat 10/18

2:05 pm-7:25 am

1 stop17h 20m

$380

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 11/8

8:48 am-4:12 pm

1 stop6h 24m

Montego Bay Sangster Intl

Sat 11/15

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 2/7

5:05 am-2:22 pm

1 stop8h 17m

Montego Bay Sangster Intl

Tue 2/10

1:12 pm-9:00 pm

1 stop8h 48m

$383

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 10/5

5:05 am-11:00 am

1 stop5h 55m

Montego Bay Sangster Intl

Thu 10/9

3:51 pm-1:06 am

2 stops33h 15m

$384

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 10/15

5:20 am-1:05 pm

1 stop7h 45m

Montego Bay Sangster Intl

Sat 10/18

2:05 pm-7:25 am

1 stop17h 20m

$385

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 11/17

9:46 am-4:34 pm

1 stop5h 48m

Montego Bay Sangster Intl

Wed 11/26

5:59 pm-12:02 am

1 stop7h 03m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 10/26

9:42 am-3:34 pm

1 stop5h 52m

Montego Bay Sangster Intl

Wed 11/5

1:48 pm-7:50 am

2 stops19h 02m

$399

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 O'Hare Intl Airport 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 O'Hare Intl Airport is in January. Flight prices, which tend to average around $516, 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 February is also cheap. Prices for this month can be found on momondo for an average of $522.

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 $540. 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 O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $681.

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 O'Hare Intl Airport 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 $608 per ticket.

What is the cheapest Chicago O'Hare Intl to Jamaica flight route?

Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $608 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Chicago O'Hare Intl Airport for as low as $535 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Jamaica flights?

There are 3 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Jamaica flights?

You could potentially save up to 19% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Jamaica flight.

Cheap Chicago O'Hare Intl Airport to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Jamaica

Best Price Found

$201

Fastest flight time

3h 59m

Direct flights

Every day

Airports in Jamaica

1 airport
The best one-way flight to Jamaica from Chicago O'Hare Intl Airport in the past 72 hours is $201. The best round-trip flight deal from Chicago O'Hare Intl Airport to Jamaica found on momondo in the last 72 hours is $491.
The fastest flight from Chicago O'Hare Intl Airport to Jamaica takes 3h 59m
Direct flights go from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Jamaica?

    Prices for flights from Chicago O'Hare Intl Airport to Jamaica are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Jamaica?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Jamaica?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Jamaica?

Best airlines flying from Chicago O'Hare Intl Airport to Jamaica

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $258Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
DeltaPriceFrom $295Free CancellationRating
7.9
7,961 reviews
Search Delta flights
United AirlinesPriceFrom $408Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $444Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jamaica?

It is quick and easy to find Chicago to Jamaica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Jamaica that suits you.

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?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Jamaica from Chicago.

I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Jamaica, momondo offers a useful price alert feature which will track prices for flights to Jamaica from Chicago and alert you when they change.

An easier way to manage your Jamaica trip

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