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Cheap flights from Chicago O'Hare Intl Airport to Jamaica from $157

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 10/10. 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 O'Hare Intl Airport to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
8:40 am - 1:48 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
4h 08mnonstop
United Airlines Logo
2:54 pm - 6:20 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 26mnonstop
$426United Airlines
Sat, Nov 14 - Fri, Nov 20
Air Canada Logo
8:50 pm - 5:20 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
19h 30m1 stop Toronto Pearson Intl
Air Canada Logo
1:50 pm - 8:00 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
19h 10m2 stops Toronto Pearson Intl Ottawa
$426Air Canada
Fri, Nov 27 - Thu, Dec 3
Air Canada Logo
10:57 am - 11:50 amORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
24h 53m2 stops Ottawa Toronto Pearson Intl
Air Canada Logo
2:20 pm - 9:23 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 03m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$426Air Canada
Wed, Oct 28 - Sun, Nov 1
American Airlines Logo
8:49 pm - 2:23 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
17h 34m1 stop Philadelphia
American Airlines Logo
2:12 pm - 6:55 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 43mnonstop
$432American Airlines
Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
8:49 pm - 2:23 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
17h 34m1 stop Philadelphia
American Airlines Logo
2:12 pm - 6:55 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
4h 43mnonstop
$432American Airlines
Sat, Aug 29 - Wed, Sep 2
Delta Logo
5:30 am - 4:35 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
10h 05m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:50 pm - 9:42 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
8h 52m1 stop New York John F Kennedy Intl
$432Delta
Mon, Dec 7 - Sat, Dec 12
Delta Logo
5:30 am - 4:35 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
10h 05m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 pm - 11:59 pmMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
6h 59m1 stop Atlanta Hartsfield-Jackson
$432Delta
Fri, Dec 4 - Tue, Dec 8
Frontier Logo
6:20 am - 2:27 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
32h 07m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson
Frontier Logo
3:42 pm - 11:51 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
20h 09m1 stop Atlanta Hartsfield-Jackson
$437Frontier
Thu, Oct 1 - Mon, Oct 5
United Airlines Logo
7:45 pm - 11:43 amORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
15h 58m1 stop Newark
United Airlines Logo
12:52 pm - 12:28 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
11h 36m1 stop Newark
$440United Airlines
Fri, Sep 11 - Fri, Sep 18
Frontier Logo
12:56 pm - 2:27 pmORD  Chicago O'Hare Intl-MBJ Montego Bay Sangster Intl
25h 31m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson
Frontier Logo
3:48 pm - 9:21 amMBJ  Montego Bay Sangster Intl-ORD Chicago O'Hare Intl
17h 33m1 stop Atlanta Hartsfield-Jackson
$464Frontier
Sat, Oct 3 - Sat, Oct 10

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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
Aug 29
ORD8:49 pmChicago O'Hare Intl
17h 34m
1 stop
MBJ2:23 pmMontego Bay Sangster Intl
Sep 2
MBJ2:12 pmMontego Bay Sangster Intl
4h 43m
ORD6:55 pmChicago O'Hare Intl
$432
American Airlines
Sep 26
ORD5:20 amChicago O'Hare Intl
7h 33m
2 stops
MBJ12:53 pmMontego Bay Sangster Intl
Oct 3
MBJ2:09 pmMontego Bay Sangster Intl
8h 22m
1 stop
ORD10:31 pmChicago O'Hare Intl
$434
American Airlines
Aug 29
ORD6:45 amChicago O'Hare Intl
7h 38m
1 stop
MBJ2:23 pmMontego Bay Sangster Intl
Sep 2
MBJ3:23 pmMontego Bay Sangster Intl
8h 21m
1 stop
ORD11:44 pmChicago O'Hare Intl
$442

Frontier flights from Chicago O'Hare Intl Airport to Jamaica

Our best Frontier deals on Chicago O'Hare Intl Airport to Jamaica flight tickets
Frontier
Oct 1
ORD6:20 amChicago O'Hare Intl
32h 07m
2 stops
MBJ2:27 pmMontego Bay Sangster Intl
Oct 5
MBJ3:42 pmMontego Bay Sangster Intl
20h 09m
1 stop
ORD11:51 amChicago O'Hare Intl
$437
Frontier
Sep 25
ORD6:20 amChicago O'Hare Intl
29h 42m
2 stops
MBJ12:02 pmMontego Bay Sangster Intl
Sep 28
MBJ3:42 pmMontego Bay Sangster Intl
31h 17m
2 stops
ORD10:59 pmChicago O'Hare Intl
$474
Frontier
Sep 30
ORD7:28 pmChicago O'Hare Intl
18h 59m
1 stop
MBJ2:27 pmMontego Bay Sangster Intl
Oct 3
MBJ1:17 pmMontego Bay Sangster Intl
29h 06m
1 stop
ORD6:23 pmChicago O'Hare Intl
$492

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 August 17, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 11/14

8:40 am-1:48 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Fri 11/20

2:54 pm-6:20 pm

Nonstop4h 26m

$426

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Fri 11/27

8:50 pm-5:20 pm

1 stop19h 30m

Montego Bay Sangster Intl

Thu 12/3

1:50 pm-8:00 am

2 stops19h 10m

$426

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Wed 10/28

10:57 am-11:50 am

2 stops24h 53m

Montego Bay Sangster Intl

Sun 11/1

2:20 pm-9:23 am

2 stops20h 03m

$426

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 8/29

8:49 pm-2:23 pm

1 stop17h 34m

Montego Bay Sangster Intl

Wed 9/2

2:12 pm-6:55 pm

Nonstop4h 43m

$432

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 8/29

8:49 pm-2:23 pm

1 stop17h 34m

Montego Bay Sangster Intl

Wed 9/2

2:12 pm-6:55 pm

Nonstop4h 43m

$432

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Mon 12/7

5:30 am-4:35 pm

1 stop10h 05m

Montego Bay Sangster Intl

Sat 12/12

1:50 pm-9:42 pm

1 stop8h 52m

$432

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Fri 12/4

5:30 am-4:35 pm

1 stop10h 05m

Montego Bay Sangster Intl

Tue 12/8

6:00 pm-11:59 pm

1 stop6h 59m

$432

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Thu 10/1

6:20 am-2:27 pm

2 stops32h 07m

Montego Bay Sangster Intl

Mon 10/5

3:42 pm-11:51 am

1 stop20h 09m

$437

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Fri 9/11

7:45 pm-11:43 am

1 stop15h 58m

Montego Bay Sangster Intl

Fri 9/18

12:52 pm-12:28 am

1 stop11h 36m

$440

ChicagoMontego Bay

ORD Chicago O'Hare Intl - MBJ Montego Bay Sangster Intl

ORDMBJ

Chicago O'Hare Intl

Sat 10/3

12:56 pm-2:27 pm

2 stops25h 31m

Montego Bay Sangster Intl

Sat 10/10

3:48 pm-9:21 am

1 stop17h 33m

$464

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 April. Flight prices, which tend to average around $464, 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 April, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $478.

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 $483. 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 $593.

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 from Chicago O'Hare Intl Airport 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 $524 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 $463 on momondo.

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

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport 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 11% 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

$157

Fastest flight time

4h 04m

Direct flights

Every day

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago O'Hare Intl Airport in the past 72 hours is $157. The best round-trip flight deal from Chicago O'Hare Intl Airport to Jamaica found on momondo in the last 72 hours is $426.
The fastest flight from Chicago O'Hare Intl Airport to Jamaica takes 4h 04m
Direct flights go from Chicago O'Hare Intl Airport to Jamaica every day.
There are 11 airports in Jamaica. From Chicago O'Hare Intl Airport there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Jamaica

  • 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
FrontierPriceFrom $144Free CancellationRating
5.6
2,675 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.8
8,503 reviews
Search Delta flights
JetBluePriceFrom $297Free CancellationRating
7.1
3,029 reviews
Search JetBlue flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
10,106 reviews
Search United Airlines flights
American AirlinesPriceFrom $317Free CancellationRating
7.1
11,944 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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