$187 Find Cheap Flights from Chicago Midway Airport to Jamaica - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Jamaica departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Midway to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$453
Kingston
Kingston2 stops$457
Montego Bay
Montego Bay1 stop$453
Kingston
Kingston2 stops$457

Book Cheap Midway to Jamaica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Jamaica that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Jamaica

Tue, Nov 3 - Tue, Nov 10
Southwest Logo
6:05 am - 2:25 pm
MDW
-
MBJ
7h 20m
1 stop
Southwest Logo
1:50 pm - 11:05 pm
MBJ
-
MDW
10h 15m
2 stops
$453Southwest
Thu, Aug 27 - Thu, Sep 3
Delta Logo
6:42 pm - 8:13 pm
MDW
-
KIN
25h 31m
2 stops
Delta Logo
9:13 am - 6:33 pm
KIN
-
MDW
9h 20m
2 stops
$457Delta
Fri, Aug 21 - Mon, Aug 24
Delta Logo
6:05 am - 8:13 pm
MDW
-
KIN
14h 08m
1 stop
Delta Logo
9:13 am - 10:36 pm
KIN
-
MDW
13h 23m
1 stop
$464Delta
Fri, Aug 21 - Fri, Aug 28
Delta Logo
6:42 pm - 8:13 pm
MDW
-
KIN
25h 31m
2 stops
Delta Logo
9:13 am - 9:17 am
KIN
-
MDW
24h 04m
2 stops
$469Delta
Wed, Jul 29 - Sun, Aug 16
Frontier Logo
6:05 am - 12:27 pm
MDW
-
MBJ
6h 22m
1 stop
Frontier Logo
1:39 pm - 10:03 pm
MBJ
-
MDW
8h 24m
1 stop
$472Frontier
Sun, Nov 15 - Fri, Nov 20
Southwest Logo
5:10 am - 12:50 pm
MDW
-
MBJ
6h 40m
1 stop
Southwest Logo
1:00 pm - 11:05 pm
MBJ
-
MDW
11h 05m
1 stop
$478Southwest
Sun, Nov 15 - Fri, Nov 20
Southwest Logo
5:05 am - 2:45 pm
MDW
-
MBJ
8h 40m
2 stops
Southwest Logo
1:00 pm - 11:05 pm
MBJ
-
MDW
11h 05m
1 stop
$483Southwest
Mon, Oct 12 - Mon, Oct 26
Frontier Logo
6:40 am - 1:31 pm
MDW
-
MBJ
6h 51m
1 stop
Frontier Logo
2:49 pm - 9:58 pm
MBJ
-
MDW
7h 09m
1 stop
$485Frontier
Sat, Oct 3 - Sat, Oct 10
Frontier Logo
7:25 am - 1:31 pm
MDW
-
MBJ
6h 06m
1 stop
Frontier Logo
2:46 pm - 9:58 pm
MBJ
-
MDW
7h 12m
1 stop
$486Frontier
Wed, Sep 9 - Sat, Sep 12
Frontier Logo
12:03 pm - 1:31 pm
MDW
-
MBJ
25h 28m
1 stop
Frontier Logo
2:49 pm - 9:58 pm
MBJ
-
MDW
7h 09m
1 stop
$491Frontier
Booking Insights

KAYAK's insights & trends for Midway to Jamaica flights

Get data-powered insights and trends into flights from Midway to Jamaica to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Jamaica flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Jamaica from Chicago Midway Airport found in the last 5 days was to Montego Bay, at $467 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $467.

What is the cheapest time of day to fly to Jamaica?

The average price for all round-trip flights from Chicago Midway Airport to Jamaica depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Jamaica is generally in the morning, when round-trip flights cost $574 on average. The most expensive time of day to fly to Jamaica is generally in the morning, which is peak travel time and where the average cost of a ticket is $574.

Can I save money by flying with a layover from Chicago Midway Airport to Jamaica?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $467, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Jamaica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Jamaica is May, when tickets cost $172 (return) on average. On the other hand, the most expensive months are July and November, when the average cost of round-trip tickets is $518 and $511 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$187
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago Midway Airport to Kingston

FAQs - booking Jamaica flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Jamaica?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Jamaica is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Jamaica?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Jamaica with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Jamaica?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Jamaica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Midway to Jamaica

Information on your arrival and departure airports

Chicago Midway Airport (MDW)