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Cheap flights from Chicago to Jamaica from $97

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 12/9. 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.
Spirit Airlines Logo
5:00 am - 1:21 pmORD-KIN
7h 21m1 stop
Spirit Airlines Logo
1:19 pm - 8:01 pmKIN-ORD
7h 42m1 stop
$342Spirit Airlines
Find Deal
Tue, Nov 25 - Sat, Dec 13
Spirit Airlines Logo
5:00 am - 12:10 pmORD-MBJ
6h 10m1 stop
Spirit Airlines Logo
3:05 pm - 12:30 amMBJ-ORD
10h 25m2 stops
$356Spirit Airlines
Find Deal
Tue, Dec 16 - Wed, Dec 24
Frontier Logo
6:00 am - 3:46 pmMDW-MBJ
8h 46m1 stop
Frontier Logo
5:06 pm - 11:25 pmMBJ-MDW
7h 19m1 stop
$356Frontier
Find Deal
Thu, Jan 8 - Sun, Jan 11
Multiple Airlines Logo
5:00 am - 12:02 pmORD-MBJ
6h 02m1 stop
Multiple Airlines Logo
2:15 pm - 3:10 pmMBJ-ORD
25h 55m1 stop
$357Multiple Airlines
Find Deal
Tue, Dec 2 - Wed, Dec 10
Multiple Airlines Logo
6:11 am - 12:10 pmORD-MBJ
28h 59m2 stops
Multiple Airlines Logo
1:05 pm - 8:01 pmMBJ-ORD
7h 56m1 stop
$358Multiple Airlines
Find Deal
Sat, Dec 13 - Tue, Dec 16
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
$364United Airlines
Find Deal
Sat, Dec 13 - Sun, Dec 21
Delta Logo
6:00 am - 2:11 pmMDW-MBJ
7h 11m1 stop
Delta Logo
3:38 pm - 10:22 pmMBJ-MDW
7h 44m1 stop
$364Delta
Find Deal
Mon, Dec 1 - Sun, Dec 21
American Airlines Logo
10:22 am - 3:29 pmORD-MBJ
4h 07mnonstop
American Airlines Logo
2:14 pm - 6:00 pmMBJ-ORD
4h 46mnonstop
$365American Airlines
Find Deal
Tue, Feb 17 - Tue, Feb 24
Delta Logo
2:35 pm - 2:13 pmORD-MBJ
22h 38m2 stops
Delta Logo
8:00 am - 12:02 amMBJ-ORD
17h 02m1 stop
$367Delta
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Mon, Dec 1 - Sun, Dec 21
Southwest Logo
5:00 am - 1:15 pmMDW-MBJ
7h 15m1 stop
Southwest Logo
3:25 pm - 11:50 pmMBJ-MDW
9h 25m2 stops
$379Southwest
Find Deal
Sat, Dec 13 - Sun, Dec 21

Delta flights from Chicago to Jamaica

Our best Delta deals on Chicago to Jamaica flight tickets
Delta
Dec 1
MDW6:00 amChicago Midway
7h 11m
1 stop
MBJ2:11 pmMontego Bay Sangster Intl
Dec 21
MBJ3:38 pmMontego Bay Sangster Intl
7h 44m
1 stop
MDW10:22 pmChicago Midway
$364
Find similar
Delta
Dec 1
ORD2:35 pmChicago O'Hare Intl
22h 38m
2 stops
MBJ2:13 pmMontego Bay Sangster Intl
Dec 21
MBJ8:00 amMontego Bay Sangster Intl
17h 02m
1 stop
ORD12:02 amChicago O'Hare Intl
$367
Find similar
Delta
Nov 28
ORD5:23 amChicago O'Hare Intl
6h 29m
1 stop
MBJ12:52 pmMontego Bay Sangster Intl
Dec 2
MBJ5:58 pmMontego Bay Sangster Intl
15h 41m
1 stop
ORD8:39 amChicago O'Hare Intl
$371
Find similar

American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets
American Airlines
Feb 17
ORD10:22 amChicago O'Hare Intl
4h 07m
MBJ3:29 pmMontego Bay Sangster Intl
Feb 24
MBJ2:14 pmMontego Bay Sangster Intl
4h 46m
ORD6:00 pmChicago O'Hare Intl
$365
Find similar
American Airlines
Dec 4
ORD5:00 amChicago O'Hare Intl
6h 55m
1 stop
MBJ12:55 pmMontego Bay Sangster Intl
Dec 11
MBJ3:12 pmMontego Bay Sangster Intl
4h 47m
ORD6:59 pmChicago O'Hare Intl
$369
Find similar
American Airlines
Dec 4
ORD5:00 amChicago O'Hare Intl
9h 53m
1 stop
MBJ3:53 pmMontego Bay Sangster Intl
Dec 7
MBJ2:30 pmMontego Bay Sangster Intl
4h 47m
ORD6:17 pmChicago O'Hare Intl
$374
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 November 13, 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 11/25

5:00 am-1:21 pm

1 stop7h 21m

Kingston Norman Manley

Sat 12/13

1:19 pm-8:01 pm

1 stop7h 42m

$342

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/16

5:00 am-12:10 pm

1 stop6h 10m

Montego Bay Sangster Intl

Wed 12/24

3:05 pm-12:30 am

2 stops10h 25m

$356

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Thu 1/8

6:00 am-3:46 pm

1 stop8h 46m

Montego Bay Sangster Intl

Sun 1/11

5:06 pm-11:25 pm

1 stop7h 19m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 12/2

5:00 am-12:02 pm

1 stop6h 02m

Montego Bay Sangster Intl

Wed 12/10

2:15 pm-3:10 pm

1 stop25h 55m

$357

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 12/13

6:11 am-12:10 pm

2 stops28h 59m

Montego Bay Sangster Intl

Tue 12/16

1:05 pm-8:01 pm

1 stop7h 56m

$358

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 12/13

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sun 12/21

2:48 pm-6:13 pm

Nonstop4h 25m

$364

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 12/1

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

Sun 12/21

3:38 pm-10:22 pm

1 stop7h 44m

$364

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/17

10:22 am-3:29 pm

Nonstop4h 07m

Montego Bay Sangster Intl

Tue 2/24

2:14 pm-6:00 pm

Nonstop4h 46m

$365

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 12/1

2:35 pm-2:13 pm

2 stops22h 38m

Montego Bay Sangster Intl

Sun 12/21

8:00 am-12:02 am

1 stop17h 02m

$367

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 12/13

5:00 am-1:15 pm

1 stop7h 15m

Montego Bay Sangster Intl

Sun 12/21

3:25 pm-11:50 pm

2 stops9h 25m

$379

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 August is also cheap. Prices for this month can be found on momondo for an average of $546.

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 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 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 $609 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 $594 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 $530 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 5% 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

$195

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 $195. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $421.
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
DeltaPriceFrom $186Free CancellationRating
7.9
8,007 reviews
Search Delta flights
Spirit AirlinesPriceFrom $194Free CancellationRating
6.3
8,139 reviews
Search Spirit Airlines flights
FrontierPriceFrom $333Free CancellationRating
5.8
3,114 reviews
Search Frontier flights
United AirlinesPriceFrom $373Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights
American AirlinesPriceFrom $433Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,236 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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