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Cheap flights from Chicago O'Hare Intl Airport to Jamaica from $114

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 1/14. 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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:10 am - 12:01 pmORD-KIN
5h 51m1 stop
Spirit Airlines Logo
2:24 pm - 11:13 pmKIN-ORD
9h 49m1 stop
$352Spirit Airlines
Find Deal
Wed, Nov 19 - Thu, Nov 20
Spirit Airlines Logo
5:05 am - 12:05 pmORD-MBJ
6h 00m1 stop
Spirit Airlines Logo
1:12 pm - 11:42 pmMBJ-ORD
11h 30m1 stop
$353Spirit Airlines
Find Deal
Sat, Feb 21 - Sat, Feb 28
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
$356United Airlines
Find Deal
Tue, Dec 2 - Sun, Dec 7
American Airlines Logo
8:05 am - 1:19 pmORD-MBJ
4h 14mnonstop
American Airlines Logo
3:12 pm - 6:51 pmMBJ-ORD
4h 39mnonstop
$357American Airlines
Find Deal
Tue, Jan 27 - Sat, Jan 31
American Airlines Logo
5:18 am - 2:59 pmORD-MBJ
8h 41m1 stop
American Airlines Logo
2:26 pm - 6:13 pmMBJ-ORD
4h 47mnonstop
$361American Airlines
Find Deal
Tue, Dec 2 - Sat, Dec 6
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
United Airlines Logo
3:36 pm - 11:32 pmMBJ-ORD
8h 56m1 stop
$367United Airlines
Find Deal
Mon, Dec 1 - Mon, Dec 8
Delta Logo
5:30 am - 12:58 pmORD-MBJ
6h 28m1 stop
Delta Logo
2:16 pm - 9:04 pmMBJ-ORD
7h 48m1 stop
$371Delta
Find Deal
Sun, Jan 4 - Fri, Jan 9
Frontier Logo
5:05 am - 3:31 pmORD-MBJ
9h 26m1 stop
Frontier Logo
4:51 pm - 10:49 amMBJ-ORD
18h 58m1 stop
$374Frontier
Find Deal
Fri, Feb 27 - Sat, Feb 28
Delta Logo
11:05 am - 8:36 pmORD-MBJ
8h 31m2 stops
Delta Logo
8:00 am - 1:39 pmMBJ-ORD
6h 39m1 stop
$376Delta
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Mon, Jan 5 - Sun, Jan 11
Frontier Logo
6:00 pm - 3:31 pmORD-MBJ
20h 31m1 stop
Frontier Logo
4:51 pm - 11:35 pmMBJ-ORD
7h 44m1 stop
$410Frontier
Find Deal
Fri, Feb 27 - Mon, Mar 2

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
Dec 2
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Dec 7
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$356
Find similar
United Airlines
Dec 1
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Dec 8
MBJ3:36 pmMontego Bay Sangster Intl
8h 56m
1 stop
ORD11:32 pmChicago O'Hare Intl
$367
Find similar
United Airlines
Feb 22
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Feb 27
MBJ3:55 pmMontego Bay Sangster Intl
8h 18m
1 stop
ORD11:13 pmChicago O'Hare Intl
$384
Find similar

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

Our best American Airlines deals on Chicago O'Hare Intl Airport to Jamaica flight tickets
American Airlines
Nov 17
ORD10:15 amChicago O'Hare Intl
4h 13m
MBJ3:28 pmMontego Bay Sangster Intl
Nov 24
MBJ3:13 pmMontego Bay Sangster Intl
4h 41m
ORD6:54 pmChicago O'Hare Intl
$356
Find similar
American Airlines
Jan 27
ORD8:05 amChicago O'Hare Intl
4h 14m
MBJ1:19 pmMontego Bay Sangster Intl
Jan 31
MBJ3:12 pmMontego Bay Sangster Intl
4h 39m
ORD6:51 pmChicago O'Hare Intl
$357
Find similar
American Airlines
Dec 2
ORD5:18 amChicago O'Hare Intl
8h 41m
1 stop
MBJ2:59 pmMontego Bay Sangster Intl
Dec 6
MBJ2:26 pmMontego Bay Sangster Intl
4h 47m
ORD6:13 pmChicago O'Hare Intl
$361
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 November 3, 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

Wed 11/19

5:10 am-12:01 pm

1 stop5h 51m

Kingston Norman Manley

Thu 11/20

2:24 pm-11:13 pm

1 stop9h 49m

$352

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 2/21

5:05 am-12:05 pm

1 stop6h 00m

Montego Bay Sangster Intl

Sat 2/28

1:12 pm-11:42 pm

1 stop11h 30m

$353

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sun 12/7

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 1/27

8:05 am-1:19 pm

Nonstop4h 14m

Montego Bay Sangster Intl

Sat 1/31

3:12 pm-6:51 pm

Nonstop4h 39m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

5:18 am-2:59 pm

1 stop8h 41m

Montego Bay Sangster Intl

Sat 12/6

2:26 pm-6:13 pm

Nonstop4h 47m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/1

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Mon 12/8

3:36 pm-11:32 pm

1 stop8h 56m

$367

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 1/4

5:30 am-12:58 pm

1 stop6h 28m

Montego Bay Sangster Intl

Fri 1/9

2:16 pm-9:04 pm

1 stop7h 48m

$371

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/27

5:05 am-3:31 pm

1 stop9h 26m

Montego Bay Sangster Intl

Sat 2/28

4:51 pm-10:49 am

1 stop18h 58m

$374

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/5

11:05 am-8:36 pm

2 stops8h 31m

Montego Bay Sangster Intl

Sun 1/11

8:00 am-1:39 pm

1 stop6h 39m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/27

6:00 pm-3:31 pm

1 stop20h 31m

Montego Bay Sangster Intl

Mon 3/2

4:51 pm-11:35 pm

1 stop7h 44m

$410

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 October. Flight prices, which tend to average around $510, 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 October, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $518.

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 $553. 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 $684.

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 $610 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 $600 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 $549 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 5% 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

$195

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 $195. The best round-trip flight deal from Chicago O'Hare Intl Airport to Jamaica found on momondo in the last 72 hours is $421.
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
DeltaPriceFrom $186Free CancellationRating
7.9
8,001 reviews
Search Delta flights
Spirit AirlinesPriceFrom $245Free CancellationRating
6.3
8,114 reviews
Search Spirit Airlines flights
FrontierPriceFrom $333Free CancellationRating
5.8
3,117 reviews
Search Frontier flights
United AirlinesPriceFrom $375Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
American AirlinesPriceFrom $433Free CancellationRating
7.2
11,036 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.

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