Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Jamaica from $100

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 3/3. 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

Enter your travel dates to find the best prices.
Spirit Airlines Logo
8:41 pm - 11:00 am
ORD
-
KIN
14h 19m
1 stop
Spirit Airlines Logo
12:17 pm - 7:46 pm
KIN
-
ORD
7h 29m
1 stop
$358Spirit Airlines
Thu, Mar 12 - Thu, Mar 19
Spirit Airlines Logo
5:15 am - 12:02 pm
ORD
-
MBJ
5h 47m
1 stop
Spirit Airlines Logo
1:00 pm - 7:11 pm
MBJ
-
ORD
7h 11m
1 stop
$365Spirit Airlines
Fri, Feb 20 - Fri, Feb 27
Multiple Airlines Logo
4:42 pm - 12:02 pm
ORD
-
MBJ
18h 20m
2 stops
Multiple Airlines Logo
1:00 pm - 7:11 pm
MBJ
-
ORD
7h 11m
1 stop
$369Multiple Airlines
Fri, Feb 20 - Fri, Feb 27
Multiple Airlines Logo
6:51 pm - 11:24 am
ORD
-
MBJ
39h 33m
2 stops
Multiple Airlines Logo
1:00 pm - 11:05 pm
MBJ
-
ORD
11h 05m
1 stop
$371Multiple Airlines
Thu, Feb 26 - Thu, Mar 5
Delta Logo
6:00 am - 3:20 pm
MDW
-
MBJ
8h 20m
1 stop
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m
1 stop
$376Delta
Tue, Feb 10 - Fri, Feb 13
Frontier Logo
8:00 am - 9:17 am
MDW
-
MBJ
24h 17m
2 stops
Frontier Logo
12:40 pm - 9:39 pm
MBJ
-
MDW
9h 59m
1 stop
$377Frontier
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
6:50 am - 2:10 pm
MDW
-
MBJ
6h 20m
1 stop
Southwest Logo
2:00 pm - 10:05 pm
MBJ
-
MDW
9h 05m
2 stops
$381Southwest
Wed, Feb 18 - Tue, Feb 24
Frontier Logo
8:00 am - 9:17 am
MDW
-
MBJ
24h 17m
2 stops
Frontier Logo
12:40 pm - 9:39 pm
MBJ
-
MDW
9h 59m
1 stop
$391Frontier
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
6:40 am - 2:10 pm
MDW
-
MBJ
6h 30m
1 stop
Southwest Logo
2:00 pm - 11:35 pm
MBJ
-
MDW
10h 35m
1 stop
$392Southwest
Sun, Mar 1 - Thu, Mar 5
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m
1 stop
Delta Logo
4:44 pm - 10:31 pm
MBJ
-
MDW
6h 47m
1 stop
$394Delta
Sat, Feb 28 - Wed, Mar 4

United Airlines flights from Chicago to Jamaica

Our best United Airlines deals on Chicago to Jamaica flight tickets
United Airlines
Mar 18
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ12:46 pmMontego Bay Sangster Intl
Mar 25
MBJ1:48 pmMontego Bay Sangster Intl
4h 25m
ORD6:13 pmChicago O'Hare Intl
$382
United Airlines
Mar 24
ORD8:42 amChicago O'Hare Intl
4h 04m
MBJ12:46 pmMontego Bay Sangster Intl
Mar 31
MBJ4:12 pmMontego Bay Sangster Intl
15h 14m
1 stop
ORD7:26 amChicago O'Hare Intl
$392
United Airlines
Feb 2
ORD2:22 pmChicago O'Hare Intl
22h 31m
1 stop
KIN1:53 pmKingston Norman Manley
Feb 6
KIN3:00 pmKingston Norman Manley
10h 04m
1 stop
ORD12:04 amChicago O'Hare Intl
$836

American Airlines flights from Chicago to Jamaica

Our best American Airlines deals on Chicago to Jamaica flight tickets
American Airlines
May 10
ORD8:10 amChicago O'Hare Intl
4h 05m
MBJ12:15 pmMontego Bay Sangster Intl
May 17
MBJ3:20 pmMontego Bay Sangster Intl
8h 33m
1 stop
ORD11:53 pmChicago O'Hare Intl
$402
American Airlines
May 10
ORD5:00 amChicago O'Hare Intl
9h 15m
1 stop
MBJ2:15 pmMontego Bay Sangster Intl
May 17
MBJ3:20 pmMontego Bay Sangster Intl
8h 33m
1 stop
ORD11:53 pmChicago O'Hare Intl
$406
American Airlines
Apr 16
ORD5:00 amChicago O'Hare Intl
6h 24m
1 stop
MBJ11:24 amMontego Bay Sangster Intl
Apr 22
MBJ1:15 pmMontego Bay Sangster Intl
4h 43m
ORD5:58 pmChicago O'Hare Intl
$411

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 January 29, 2026.
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

Thu 3/12

8:41 pm-11:00 am

1 stop14h 19m

Kingston Norman Manley

Thu 3/19

12:17 pm-7:46 pm

1 stop7h 29m

$358

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/20

5:15 am-12:02 pm

1 stop5h 47m

Montego Bay Sangster Intl

Fri 2/27

1:00 pm-7:11 pm

1 stop7h 11m

$365

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 2/20

4:42 pm-12:02 pm

2 stops18h 20m

Montego Bay Sangster Intl

Fri 2/27

1:00 pm-7:11 pm

1 stop7h 11m

$369

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 2/26

6:51 pm-11:24 am

2 stops39h 33m

Montego Bay Sangster Intl

Thu 3/5

1:00 pm-11:05 pm

1 stop11h 05m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 2/10

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

Fri 2/13

4:44 pm-10:31 pm

1 stop6h 47m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/21

8:00 am-9:17 am

2 stops24h 17m

Montego Bay Sangster Intl

Sat 2/28

12:40 pm-9:39 pm

1 stop9h 59m

$377

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 2/18

6:50 am-2:10 pm

1 stop6h 20m

Montego Bay Sangster Intl

Tue 2/24

2:00 pm-10:05 pm

2 stops9h 05m

$381

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/21

8:00 am-9:17 am

2 stops24h 17m

Montego Bay Sangster Intl

Sat 2/28

12:40 pm-9:39 pm

1 stop9h 59m

$391

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/1

6:40 am-2:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Thu 3/5

2:00 pm-11:35 pm

1 stop10h 35m

$392

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 2/28

6:00 am-3:19 pm

1 stop8h 19m

Montego Bay Sangster Intl

Wed 3/4

4:44 pm-10:31 pm

1 stop6h 47m

$394

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 January. Flight prices, which tend to average around $529, 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 January, 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 Tuesday when prices can be found for as low as $543. 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 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 week ahead of your departure date. In general, you can expect to find flights to Jamaica for around $578 when searching week 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 $500 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?

No. A direct flight is the cheapest option for a flight between Chicago to Jamaica.

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

$248

Fastest flight time

3h 45m

Direct flights

Every day

Airports in Jamaica

11 airports
The best one-way flight to Jamaica from Chicago in the past 72 hours is $248. The best round-trip flight deal from Chicago to Jamaica found on momondo in the last 72 hours is $480.
The fastest flight from Chicago to Jamaica takes 3h 45m
Direct flights go from Chicago to Jamaica every day.
There are 11 airports in Jamaica. From Chicago there are direct flights to 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 $100Free CancellationRating
6.3
8,394 reviews
Search Spirit Airlines flights
FrontierPriceFrom $144Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
DeltaPriceFrom $178Free CancellationRating
7.9
8,127 reviews
Search Delta flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $419Free CancellationRating
7.2
11,206 reviews
Search American Airlines flights
SouthwestPriceFrom $531Free CancellationRating
8.0
4,267 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
Sat 2/28
Sat 3/7
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 $215
Flights to Kingstonfrom $247
Flights to Ocho Rios