Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Jamaica from $137

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 Midway Airport to Jamaica departing on 7/21. 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 Midway Airport to Jamaica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:05 am - 1:01 pm
MDW
-
MBJ
6h 56m
1 stop
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
$352Delta
Sat, Aug 15 - Fri, Aug 21
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
2:26 pm - 9:17 am
MBJ
-
MDW
18h 51m
2 stops
$357Delta
Sat, Aug 15 - Thu, Aug 27
Delta Logo
6:00 am - 1:04 pm
MDW
-
MBJ
7h 04m
1 stop
Delta Logo
1:25 pm - 9:46 pm
MBJ
-
MDW
8h 21m
1 stop
$399Delta
Tue, Sep 8 - Sat, Sep 12
Delta Logo
6:00 am - 4:35 pm
MDW
-
MBJ
9h 35m
1 stop
Delta Logo
3:40 pm - 9:45 pm
MBJ
-
MDW
7h 05m
1 stop
$420Delta
Wed, Nov 11 - Wed, Nov 18
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
1:25 pm - 10:25 pm
MBJ
-
MDW
9h 00m
1 stop
$433Delta
Sat, Sep 19 - Sat, Sep 26
Delta Logo
6:00 am - 4:35 pm
MDW
-
MBJ
9h 35m
1 stop
Delta Logo
3:40 pm - 9:45 pm
MBJ
-
MDW
7h 05m
1 stop
$440Delta
Wed, Nov 18 - Wed, Nov 25
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
2:26 pm - 10:36 pm
MBJ
-
MDW
8h 10m
1 stop
$443Delta
Sun, Aug 9 - Sat, Aug 15
Southwest Logo
7:15 am - 1:15 pm
MDW
-
MBJ
6h 00m
1 stop
Southwest Logo
12:55 pm - 11:10 pm
MBJ
-
MDW
10h 15m
2 stops
$445Southwest
Fri, Aug 14 - Tue, Aug 18
Delta Logo
6:00 am - 3:34 pm
MDW
-
MBJ
9h 34m
1 stop
Delta Logo
1:32 pm - 9:45 pm
MBJ
-
MDW
8h 13m
1 stop
$446Delta
Sun, Oct 18 - Fri, Oct 23
Delta Logo
6:05 am - 1:01 pm
MDW
-
MBJ
6h 56m
1 stop
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
$452Delta
Sun, Aug 16 - Thu, Aug 20

Delta flights from Chicago Midway Airport to Jamaica

Our best Delta deals on Chicago Midway Airport to Jamaica flight tickets
Delta
Aug 15
MDW6:05 amChicago Midway
6h 56m
1 stop
MBJ1:01 pmMontego Bay Sangster Intl
Aug 21
MBJ2:26 pmMontego Bay Sangster Intl
8h 10m
1 stop
MDW10:36 pmChicago Midway
$352
Delta
Aug 15
MDW6:05 amChicago Midway
9h 29m
1 stop
MBJ3:34 pmMontego Bay Sangster Intl
Aug 27
MBJ2:26 pmMontego Bay Sangster Intl
18h 51m
2 stops
MDW9:17 amChicago Midway
$357
Delta
Sep 8
MDW6:00 amChicago Midway
5h 49m
1 stop
MBJ11:49 amMontego Bay Sangster Intl
Sep 12
MBJ1:25 pmMontego Bay Sangster Intl
8h 21m
1 stop
MDW9:46 pmChicago Midway
$369

Southwest flights from Chicago Midway Airport to Jamaica

Our best Southwest deals on Chicago Midway Airport to Jamaica flight tickets
Southwest
Aug 14
MDW7:15 amChicago Midway
6h 00m
1 stop
MBJ1:15 pmMontego Bay Sangster Intl
Aug 18
MBJ12:55 pmMontego Bay Sangster Intl
10h 15m
2 stops
MDW11:10 pmChicago Midway
$445
Southwest
Jul 4
MDW10:10 amChicago Midway
3h 50m
MBJ2:00 pmMontego Bay Sangster Intl
Jul 11
MBJ2:30 pmMontego Bay Sangster Intl
8h 45m
1 stop
MDW11:15 pmChicago Midway
$456
Southwest
May 30
MDW5:15 amChicago Midway
5h 55m
1 stop
MBJ11:10 amMontego Bay Sangster Intl
Jun 6
MBJ2:30 pmMontego Bay Sangster Intl
4h 05m
MDW6:35 pmChicago Midway
$472

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway 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 May 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/15

6:05 am-1:01 pm

1 stop6h 56m

Montego Bay Sangster Intl

Fri 8/21

2:26 pm-10:36 pm

1 stop8h 10m

$352

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 8/15

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Thu 8/27

2:26 pm-9:17 am

2 stops18h 51m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 9/8

6:00 am-1:04 pm

1 stop7h 04m

Montego Bay Sangster Intl

Sat 9/12

1:25 pm-9:46 pm

1 stop8h 21m

$399

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 11/11

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Wed 11/18

3:40 pm-9:45 pm

1 stop7h 05m

$420

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/19

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Sat 9/26

1:25 pm-10:25 pm

1 stop9h 00m

$433

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Wed 11/18

6:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Wed 11/25

3:40 pm-9:45 pm

1 stop7h 05m

$440

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/9

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Sat 8/15

2:26 pm-10:36 pm

1 stop8h 10m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 8/14

7:15 am-1:15 pm

1 stop6h 00m

Montego Bay Sangster Intl

Tue 8/18

12:55 pm-11:10 pm

2 stops10h 15m

$445

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 10/18

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Fri 10/23

1:32 pm-9:45 pm

1 stop8h 13m

$446

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

6:05 am-1:01 pm

1 stop6h 56m

Montego Bay Sangster Intl

Thu 8/20

1:09 pm-10:36 pm

1 stop9h 27m

$452

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 Midway 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 Midway Airport is in May. Flight prices, which tend to average around $172, 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 May, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $341.

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 $518. 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 Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $904.

What is the cheapest Chicago Midway to Jamaica flight route?

Fly from Chicago Midway to Montego Bay Sangster Intl for the best Chicago Midway - Jamaica flight prices

What cabin class options are available on Chicago Midway Airport to Jamaica flights?

There is only 1 cabin class available to choose from on Chicago Midway 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 Midway Airport to Jamaica flights?

You could potentially save up to 21% on your flight if you consider stops on a Chicago Midway Airport to Jamaica flight.

Cheap Chicago Midway Airport to Jamaica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Jamaica

Best Price Found

$497

Fastest flight time

3h 55m

Direct flights

Mon and Sun

Airports in Jamaica

11 airports
The best flight deal from Chicago Midway Airport to Jamaica found on momondo in the last 72 hours is $497
The fastest flight from Chicago Midway Airport to Jamaica takes 3h 55m
Direct flights go from Chicago Midway Airport to Jamaica on Monday and Sunday. There are no airlines offering direct flights.
There are 11 airports in Jamaica. From Chicago Midway Airport there are direct flights to Montego Bay Sangster Intl (MBJ).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Jamaica

  • When did momondo last update prices for flights from Chicago Midway Airport to Jamaica?

    Prices for flights from Chicago Midway Airport to Jamaica were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Jamaica?

  • How old do you have to be to fly from Chicago Midway 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 Midway 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 Midway Airport to Jamaica?

Best airlines flying from Chicago Midway Airport to Jamaica

Compare and see reviews for airlines that fly from Chicago Midway Airport to Jamaica with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $172Free CancellationRating
5.6
2,929 reviews
Search Frontier flights
DeltaPriceFrom $395Free CancellationRating
7.9
8,419 reviews
Search Delta flights
SouthwestPriceFrom $468Free CancellationRating
8.0
4,264 reviews
Search Southwest 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?

Yes. momondo enables you to select and highlight flights to Jamaica from Chicago with this policy.

How can momondo help me find flights from Chicago to Jamaica?

momondo helps you find the best flight between Chicago and Jamaica by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Jamaica right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Jamaica flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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
Sun 6/28
Sun 7/5
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 $302
Flights to Kingstonfrom $386
Flights to Ocho Rios