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Cheap flights from Chicago to Jamaica from $118

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 12/11. 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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0 bags

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Find the cheapest flights from Chicago to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:15 pm - 12:05 pmORD-MBJ
15h 50m2 stops
Multiple Airlines Logo
7:00 pm - 12:51 pmMBJ-ORD
18h 51m1 stop
$354Multiple Airlines
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Fri, Feb 6 - Wed, Feb 18
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
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Mon, Dec 8 - Tue, Dec 9
American Airlines Logo
8:05 am - 1:18 pmORD-MBJ
4h 13mnonstop
American Airlines Logo
1:58 pm - 5:37 pmMBJ-ORD
4h 39mnonstop
$357American Airlines
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Mon, Jan 5 - Mon, Jan 12
Spirit Airlines Logo
3:26 pm - 12:02 pmORD-MBJ
19h 36m1 stop
Spirit Airlines Logo
1:07 pm - 11:13 pmMBJ-ORD
11h 06m1 stop
$358Spirit Airlines
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Wed, Nov 19 - Sun, Nov 23
Spirit Airlines Logo
3:26 pm - 12:05 pmORD-MBJ
19h 39m1 stop
Spirit Airlines Logo
1:12 pm - 9:00 pmMBJ-ORD
8h 48m1 stop
$360Spirit Airlines
Find Deal
Mon, Jan 5 - Wed, Jan 14
American Airlines Logo
6:35 pm - 12:54 pmORD-MBJ
17h 19m1 stop
American Airlines Logo
2:30 pm - 6:17 pmMBJ-ORD
4h 47mnonstop
$361American Airlines
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Fri, Nov 28 - Thu, Dec 4
Delta Logo
7:35 pm - 12:45 pmORD-MBJ
16h 10m1 stop
Delta Logo
2:10 pm - 8:38 pmMBJ-ORD
7h 28m1 stop
$371Delta
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Fri, Jan 23 - Wed, Jan 28
Delta Logo
10:35 am - 8:25 pmMDW-MBJ
8h 50m1 stop
Delta Logo
2:05 pm - 9:46 pmMBJ-MDW
8h 41m1 stop
$371Delta
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Sat, Jan 10 - Sat, Jan 17
Southwest Logo
5:00 am - 2:55 pmMDW-MBJ
8h 55m2 stops
Southwest Logo
1:50 pm - 11:00 pmMBJ-MDW
10h 10m1 stop
$438Southwest
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Mon, Nov 3 - Fri, Nov 7
Southwest Logo
5:20 am - 3:15 pmMDW-MBJ
8h 55m2 stops
Southwest Logo
2:00 pm - 9:00 pmMBJ-MDW
8h 00m1 stop
$447Southwest
Find Deal
Mon, Jan 19 - Thu, Jan 22

Southwest flights from Chicago to Jamaica

Our best Southwest deals on Chicago to Jamaica flight tickets
Southwest
Nov 3
MDW5:00 amChicago Midway
8h 55m
2 stops
MBJ2:55 pmMontego Bay Sangster Intl
Nov 7
MBJ1:50 pmMontego Bay Sangster Intl
10h 10m
1 stop
MDW11:00 pmChicago Midway
$438
Find similar
Southwest
Jan 19
MDW5:20 amChicago Midway
8h 55m
2 stops
MBJ3:15 pmMontego Bay Sangster Intl
Jan 22
MBJ2:00 pmMontego Bay Sangster Intl
8h 00m
1 stop
MDW9:00 pmChicago Midway
$447
Find similar
Southwest
Oct 25
MDW6:50 amChicago Midway
7h 00m
1 stop
MBJ1:50 pmMontego Bay Sangster Intl
Oct 31
MBJ12:40 pmMontego Bay Sangster Intl
8h 30m
1 stop
MDW9:10 pmChicago Midway
$469
Find similar

United Airlines flights from Chicago to Jamaica

Our best United Airlines deals on Chicago to Jamaica flight tickets
United Airlines
Dec 8
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Dec 9
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$356
Find similar
United Airlines
Nov 15
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Nov 20
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$381
Find similar
United Airlines
Dec 17
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ1:46 pmMontego Bay Sangster Intl
Dec 23
MBJ2:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$383
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 October 24, 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

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/6

7:15 pm-12:05 pm

2 stops15h 50m

Montego Bay Sangster Intl

Wed 2/18

7:00 pm-12:51 pm

1 stop18h 51m

$354

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/8

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Tue 12/9

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/5

8:05 am-1:18 pm

Nonstop4h 13m

Montego Bay Sangster Intl

Mon 1/12

1:58 pm-5:37 pm

Nonstop4h 39m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 11/19

3:26 pm-12:02 pm

1 stop19h 36m

Montego Bay Sangster Intl

Sun 11/23

1:07 pm-11:13 pm

1 stop11h 06m

$358

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 1/5

3:26 pm-12:05 pm

1 stop19h 39m

Montego Bay Sangster Intl

Wed 1/14

1:12 pm-9:00 pm

1 stop8h 48m

$360

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 11/28

6:35 pm-12:54 pm

1 stop17h 19m

Montego Bay Sangster Intl

Thu 12/4

2:30 pm-6:17 pm

Nonstop4h 47m

$361

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 1/23

7:35 pm-12:45 pm

1 stop16h 10m

Montego Bay Sangster Intl

Wed 1/28

2:10 pm-8:38 pm

1 stop7h 28m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 1/10

10:35 am-8:25 pm

1 stop8h 50m

Montego Bay Sangster Intl

Sat 1/17

2:05 pm-9:46 pm

1 stop8h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 11/3

5:00 am-2:55 pm

2 stops8h 55m

Montego Bay Sangster Intl

Fri 11/7

1:50 pm-11:00 pm

1 stop10h 10m

$438

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 1/19

5:20 am-3:15 pm

2 stops8h 55m

Montego Bay Sangster Intl

Thu 1/22

2:00 pm-9:00 pm

1 stop8h 00m

$447

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 September. Flight prices, which tend to average around $540, 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 September, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $542.

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 $548. 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 $683.

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 $610 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 $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 for as low as $554 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 20% 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

$242

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Jamaica

1 airport
The best one-way flight to Jamaica from Chicago in the past 72 hours is $242. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $425.
The fastest flight from Chicago to Jamaica takes 3h 50m
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 $245Free CancellationRating
6.3
8,111 reviews
Search Spirit Airlines flights
FrontierPriceFrom $333Free CancellationRating
5.8
3,126 reviews
Search Frontier flights
DeltaPriceFrom $369Free CancellationRating
7.9
7,986 reviews
Search Delta flights
United AirlinesPriceFrom $376Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
American AirlinesPriceFrom $433Free CancellationRating
7.2
11,032 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,237 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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