$245 Find Cheap Flights from Jamaica to Chicago Midway Airport - 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 to Midway departing on 9/2. 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 Jamaica to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jamaica to Midway 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 Jamaica to Midway

Sun, Sep 13 - Mon, Sep 14
Frontier Logo
3:42 pm - 11:44 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 02m1 stop Atlanta Hartsfield-Jackson
$458Frontier
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
1:55 pm - 8:45 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
6h 50m1 stop Baltimore/Washington
Southwest Logo
6:30 am - 12:55 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 25m1 stop Baltimore/Washington
$469Southwest
Thu, Sep 17 - Thu, Sep 24
Frontier Logo
3:42 pm - 11:44 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:46 pm - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
19h 41m1 stop Atlanta Hartsfield-Jackson
$475Frontier
Sat, Aug 22 - Mon, Sep 28
Frontier Logo
1:32 pm - 10:47 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 2:27 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
8h 02m1 stop Atlanta Hartsfield-Jackson
$484Frontier
Sun, Sep 13 - Sat, Sep 19
Southwest Logo
2:00 pm - 10:30 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 30m1 stop Baltimore/Washington
Southwest Logo
5:55 am - 12:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 30m1 stop Baltimore/Washington
$491Southwest
Sun, Sep 13 - Sat, Sep 19
Southwest Logo
12:45 pm - 10:30 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
9h 45m1 stop Baltimore/Washington
Southwest Logo
5:55 am - 12:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 30m1 stop Baltimore/Washington
$491Southwest
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
12:55 pm - 11:10 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
10h 15m2 stops Orlando Houston Hobby
Southwest Logo
6:30 am - 12:55 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 25m1 stop Baltimore/Washington
$544Southwest
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
12:55 pm - 9:00 pmMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
8h 05m1 stop Orlando
Southwest Logo
6:30 am - 12:55 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 25m1 stop Baltimore/Washington
$546Southwest
Sun, Sep 13 - Sat, Sep 19
Southwest Logo
2:00 pm - 8:45 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
18h 45m2 stops Baltimore/Washington Orlando
Southwest Logo
5:55 am - 12:25 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
6h 30m1 stop Baltimore/Washington
$554Southwest
Thu, Sep 17 - Thu, Sep 24
Delta Logo
4:50 pm - 9:07 amMBJ  Montego Bay Sangster Intl-MDW Chicago Midway
16h 17m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:05 am - 3:35 pmMDW  Chicago Midway-MBJ Montego Bay Sangster Intl
9h 30m1 stop Atlanta Hartsfield-Jackson
$572Delta
Booking Insights

KAYAK's insights & trends for flights to Midway

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

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where round-trip tickets can be as cheap as $473. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $473 on average.

What is the cheapest time of day to fly to Chicago Midway Airport?

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

The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when round-trip flights cost $473 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $763.

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Good to know

Cheapest flight

$245
Flight from Montego Bay to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    Chicago Midway Airport is 9 miles from the center of Chicago.

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

    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 to Chicago Midway Airport.

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

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

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

    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 to Chicago Midway Airport 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 to Chicago Midway Airport?

    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 to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 2,572 direct flights from within Jamaica to Chicago Midway Airport. The most common day for departures is Friday, with 20% of flights taking off on this day.

Top tips for finding cheap flights to Chicago Midway Airport

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)