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$242+ Cheap flights from St. John's (YYT) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from St. John's to Midway

Discover tips and strategies to find the most affordable flight options for your journey from St. John's (YYT) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 8, 2026.

Round-trip from

$436
(Trip.com)

One-way from

$242
(Mytrip)
From St John's to Chicago Midway
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One-way flight from St John's to Chicago Midway
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Find flight deals from St. John's to Midway

Cheapest flights from St. John's to Midway
Explore the most affordable flight options available from St. John's to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.

This Trip.com deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 amYYT - MDW
2 stops11h 50mPorter Airlines
Mon 4/2711:00 amMDW - YYT
2 stops9h 35mPorter Airlines
Deal found 1/6$436
This FlightHub deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 amYYT - MDW
2 stops11h 50mPorter Airlines
Wed 4/2911:00 amMDW - YYT
2 stops9h 35mPorter Airlines
Deal found 1/6$437
This FlightHub deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 amYYT - MDW
1 stop11h 50mPorter Airlines
Thu 3/1911:00 amMDW - YYT
1 stop9h 35mPorter Airlines
Deal found 1/7$463
This FlightHub deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 amYYT - MDW
2 stops11h 50mPorter Airlines
Sun 4/2611:00 amMDW - YYT
2 stops9h 35mPorter Airlines
Deal found 1/6$481
This FlightHub deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 amYYT - MDW
2 stops11h 50mPorter Airlines
Sun 4/2611:00 amMDW - YYT
2 stops9h 35mPorter Airlines
Deal found 1/6$524
This Porter Airlines deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/156:00 amYYT - MDW
2 stops30h 35mPorter Airlines
Mon 1/1911:00 amMDW - YYT
2 stops11h 31mPorter Airlines
Deal found 1/7$787

Cheapflights Fare Finder

 
Customize your flight search to find flights from St. John's to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated January 8, 2026.
Use the filters below to find and compare flights from St. John's to Chicago Midway Airport that are best for you.

Fly from

St. John's

Fly to

Midway

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/23

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Mon 4/27

11:00 am-11:05 pm

2 stops9h 35m

$436

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/22

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Mon 4/27

11:00 am-11:05 pm

2 stops9h 35m

$437

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/22

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Tue 4/28

11:00 am-11:05 pm

2 stops9h 35m

$437

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 4/24

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Tue 4/28

11:00 am-11:05 pm

2 stops9h 35m

$437

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 4/24

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Wed 4/29

11:00 am-11:05 pm

2 stops9h 35m

$437

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/22

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Wed 4/29

11:00 am-11:05 pm

2 stops9h 35m

$437

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 3/15

6:00 am-3:20 pm

1 stop11h 50m

Chicago Midway

Thu 3/19

11:00 am-11:05 pm

1 stop9h 35m

$463

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 4/24

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Sun 4/26

11:00 am-11:05 pm

2 stops9h 35m

$481

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/23

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Wed 4/29

11:00 am-11:05 pm

2 stops9h 35m

$481

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/22

6:00 am-3:20 pm

2 stops11h 50m

Chicago Midway

Sun 4/26

11:00 am-11:05 pm

2 stops9h 35m

$481

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 12 results
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Best time to book a flight from St. John's to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from St. John's with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from St. John's to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from St. John's to Chicago Midway?

    St John's (YYT), located 4.2 mi from the city center, is the airport you fly out of when you book flights from St. John's to Chicago Midway. 0 airlines have flights from St John's to Chicago Midway on a regular basis. Booking flights from St John's to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • How long is the flight from St. John's to Chicago Midway Airport?

    Porter Airlines can get you from St. John's to Chicago Midway Airport in just under 11h 50m. Your travel time can differ by up to . The distance from St. John's to Chicago Midway Airport is about 1748 mi.

  • Can I find deals for flights from St. John's to Midway that include hotel bookings?

    Yes. In addition to deals on St. John's to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from St. John's to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. John's to Midway.

  • Can I find deals for business class flights from St. John's to Midway?

    Yes. Cheapflights offers flight deals from St. John's to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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