Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago 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 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.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago 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 - 11:42 pmKIN-ORD
11h 14m1 stop
$342Spirit Airlines
Find Deal
sáb., nov. 8 - jue., nov. 13
Spirit Airlines Logo
6:18 pm - 11:09 amORD-KIN
16h 51m2 stops
Spirit Airlines Logo
12:14 pm - 1:03 amKIN-ORD
12h 49m1 stop
$369Spirit Airlines
Find Deal
jue., oct. 23 - lun., oct. 27
American Airlines Logo
10:15 am - 3:28 pmORD-MBJ
4h 13mnonstop
American Airlines Logo
3:13 pm - 6:54 pmMBJ-ORD
4h 41mnonstop
$376American Airlines
Find Deal
sáb., nov. 8 - mié., nov. 12
American Airlines Logo
8:44 am - 12:45 pmORD-MBJ
4h 01mnonstop
American Airlines Logo
4:05 pm - 10:54 pmMBJ-ORD
6h 49m1 stop
$380American Airlines
Find Deal
mar., oct. 14 - mar., oct. 21
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
sáb., nov. 8 - sáb., nov. 15
Delta Logo
6:00 am - 1:09 pmMDW-MBJ
7h 09m1 stop
Delta Logo
1:25 pm - 9:36 pmMBJ-MDW
8h 11m1 stop
$385Delta
Find Deal
lun., sep. 29 - jue., oct. 2
Southwest Logo
8:45 pm - 2:00 pmMDW-MBJ
17h 15m2 stops
Southwest Logo
1:00 pm - 10:35 pmMBJ-MDW
9h 35m1 stop
$389Southwest
Find Deal
vie., oct. 3 - mar., oct. 7
United Airlines Logo
8:42 am - 1:46 pmORD-MBJ
4h 04mnonstop
United Airlines Logo
2:48 pm - 6:13 pmMBJ-ORD
4h 25mnonstop
$390United Airlines
Find Deal
mar., feb. 17 - mié., feb. 25
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
lun., nov. 17 - mié., nov. 26
Southwest Logo
5:35 am - 2:55 pmMDW-MBJ
8h 20m2 stops
Southwest Logo
1:50 pm - 11:05 pmMBJ-MDW
10h 15m2 stops
$395Southwest
Find Deal
mié., nov. 19 - mar., nov. 25

JetBlue flights from Chicago to Jamaica

Our best JetBlue deals on Chicago to Jamaica flight tickets
JetBlue
Oct 20
ORD6:45 amChicago O'Hare Intl
8h 39m
1 stop
MBJ3:24 pmMontego Bay Sangster Intl
Oct 28
MBJ7:00 amMontego Bay Sangster Intl
13h 52m
1 stop
ORD8:52 pmChicago O'Hare Intl
$419
Find similar
JetBlue
Sep 29
ORD6:45 amChicago O'Hare Intl
17h 59m
1 stop
KIN12:44 amKingston Norman Manley
Oct 1
KIN2:47 amKingston Norman Manley
18h 02m
1 stop
ORD8:49 pmChicago O'Hare Intl
$559
Find similar
JetBlue
Sep 22
ORD6:45 amChicago O'Hare Intl
11h 49m
1 stop
KIN6:34 pmKingston Norman Manley
Sep 28
KIN2:10 amKingston Norman Manley
18h 39m
1 stop
ORD8:49 pmChicago O'Hare Intl
$733
Find similar

Frontier flights from Chicago to Jamaica

Our best Frontier deals on Chicago to Jamaica flight tickets
Frontier
Oct 30
MDW6:20 amChicago Midway
8h 55m
1 stop
MBJ3:15 pmMontego Bay Sangster Intl
Nov 6
MBJ4:30 pmMontego Bay Sangster Intl
27h 09m
1 stop
MDW6:39 pmChicago Midway
$380
Find similar
Frontier
Dec 7
MDW6:00 amChicago Midway
8h 33m
1 stop
MBJ3:33 pmMontego Bay Sangster Intl
Dec 13
MBJ4:53 pmMontego Bay Sangster Intl
7h 12m
1 stop
MDW11:05 pmChicago Midway
$388
Find similar
Frontier
Oct 23
MDW9:26 pmChicago Midway
17h 10m
1 stop
MBJ2:36 pmMontego Bay Sangster Intl
Oct 26
MBJ3:51 pmMontego Bay Sangster Intl
7h 55m
1 stop
MDW11:46 pmChicago Midway
$390
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 septiembre 16, 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

sáb. 11/8

5:59 pm-12:13 pm

1 stop17h 14m

Kingston Norman Manley

jue. 11/13

1:28 pm-11:42 pm

1 stop11h 14m

$342

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

jue. 10/23

6:18 pm-11:09 am

2 stops16h 51m

Kingston Norman Manley

lun. 10/27

12:14 pm-1:03 am

1 stop12h 49m

$369

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 11/8

10:15 am-3:28 pm

Nonstop4h 13m

Montego Bay Sangster Intl

mié. 11/12

3:13 pm-6:54 pm

Nonstop4h 41m

$376

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 10/14

8:44 am-12:45 pm

Nonstop4h 01m

Montego Bay Sangster Intl

mar. 10/21

4:05 pm-10:54 pm

1 stop6h 49m

$380

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 11/8

8:48 am-4:12 pm

1 stop6h 24m

Montego Bay Sangster Intl

sáb. 11/15

2:48 pm-6:13 pm

Nonstop4h 25m

$381

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 9/29

6:00 am-1:09 pm

1 stop7h 09m

Montego Bay Sangster Intl

jue. 10/2

1:25 pm-9:36 pm

1 stop8h 11m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

vie. 10/3

8:45 pm-2:00 pm

2 stops17h 15m

Montego Bay Sangster Intl

mar. 10/7

1:00 pm-10:35 pm

1 stop9h 35m

$389

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 2/17

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

mié. 2/25

2:48 pm-6:13 pm

Nonstop4h 25m

$390

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 11/17

9:46 am-4:34 pm

1 stop5h 48m

Montego Bay Sangster Intl

mié. 11/26

5:59 pm-12:02 am

1 stop7h 03m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mié. 11/19

5:35 am-2:55 pm

2 stops8h 20m

Montego Bay Sangster Intl

mar. 11/25

1:50 pm-11:05 pm

2 stops10h 15m

$395

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 February. 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 February, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $540.

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 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 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 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 $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 for as low as $535 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 19% 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

$201

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 $201. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $491.
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 $258Free CancellationRating
6.3
8,019 reviews
Search Spirit Airlines flights
DeltaPriceFrom $295Free CancellationRating
7.9
7,957 reviews
Search Delta flights
FrontierPriceFrom $370Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
United AirlinesPriceFrom $408Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
American AirlinesPriceFrom $444Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $549Free CancellationRating
8.0
4,242 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
jue. 10/16
jue. 10/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Jamaica

Popular cities in Jamaica

Popular flights according to clicks in the last 7 days on momondo
Flights to Montego Bayfrom $211
Flights to Kingstonfrom $242
Flights to Ocho Rios