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Midway

$417+ Cheap flights from Newfoundland and Labrador to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Newfoundland and Labrador to Midway

Cheapest flights from Newfoundland and Labrador to Midway
Explore the most affordable flight options available from Newfoundland and Labrador to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This FlightHub deal was found by Cheapflights users on 1/25. 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.
Tue 4/216:20 am
YYT
-
MDW
2 stops11h 30m
Porter Airlines
Sun 4/2611:00 am
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Deal found 1/25$417
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:20 am
YYT
-
MDW
2 stops30h 15m
Multiple Airlines
Mon 4/2711:00 am
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 1/25$423
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:20 am
YYT
-
MDW
2 stops30h 15m
Multiple Airlines
Sun 4/2611:00 am
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 1/25$426
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:40 pm
YYT
-
MDW
1 stop18h 55m
Multiple Airlines
Tue 4/284:15 pm
MDW
-
YYT
1 stop28h 10m
Multiple Airlines
Deal found 1/25$431
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:40 pm
YYT
-
MDW
1 stop18h 55m
Multiple Airlines
Sun 4/2611:00 am
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 1/25$433
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:40 pm
YYT
-
MDW
1 stop18h 55m
Porter Airlines
Sun 4/2611:00 am
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Deal found 1/25$450
This FlightHub deal was found by Cheapflights users on 1/25. 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 am
YYT
-
MDW
2 stops11h 50m
Porter Airlines
Tue 4/2811:00 am
MDW
-
YYT
2 stops9h 35m
Porter Airlines
Deal found 1/25$453
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:15 pm
YYT
-
MDW
2 stops20h 20m
Multiple Airlines
Mon 4/2711:00 am
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 1/26$455
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:40 pm
YYT
-
MDW
1 stop18h 55m
Porter Airlines
Mon 4/2711:00 am
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Deal found 1/25$457
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:20 am
YYT
-
MDW
2 stops11h 30m
Multiple Airlines
Tue 4/284:15 pm
MDW
-
YYT
1 stop28h 10m
Multiple Airlines
Deal found 1/25$458
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:20 am
YYT
-
MDW
2 stops11h 30m
Multiple Airlines
Sun 4/2611:00 am
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 1/25$460
This FlightHub deal was found by Cheapflights users on 1/26. 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 4/236:20 am
YYT
-
MDW
2 stops11h 30m
Porter Airlines
Tue 4/2811:00 am
MDW
-
YYT
2 stops9h 35m
Porter Airlines
Deal found 1/26$463

Find flight deals from Newfoundland and Labrador to Midway

Keep the following information in mind while searching for Newfoundland and Labrador to Midway flight deals. Data was last updated January 27, 2026.

Round-trip from

$417
(FlightHub)
From Newfoundland and Labrador to Chicago Midway
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Newfoundland and Labrador 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 27, 2026.
Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago Midway Airport that are best for you.

Fly from

Newfoundland and Labrador

Fly to

Midway

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 4/21

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Sun 4/26

11:00 am-1:01 am

2 stops11h 31m

$417

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 4/21

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Mon 4/27

11:00 am-11:05 pm

2 stops9h 35m

$417

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 4/21

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Tue 4/28

11:00 am-11:05 pm

2 stops9h 35m

$417

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 4/21

6:20 am-10:05 am

2 stops30h 15m

Chicago Midway

Tue 4/28

11:00 am-10:55 pm

1 stop9h 25m

$423

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 4/21

6:20 am-10:05 am

2 stops30h 15m

Chicago Midway

Sun 4/26

11:00 am-10:55 pm

1 stop9h 25m

$426

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/22

5:40 pm-3:20 pm

1 stop24h 10m

Chicago Midway

Mon 4/27

11:00 am-10:55 pm

1 stop9h 25m

$431

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/22

5:40 pm-10:05 am

1 stop18h 55m

Chicago Midway

Tue 4/28

4:15 pm-10:55 pm

1 stop28h 10m

$431

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 4/22

6:20 am-3:20 pm

2 stops11h 30m

Chicago Midway

Sun 4/26

11:00 am-1:01 am

2 stops11h 31m

$453

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

$453

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

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 12 results
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Best time to book a flight from Newfoundland and Labrador to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Newfoundland and Labrador 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.

Cheapflights Insights

Everything you need to know about your flight from Newfoundland and Labrador to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

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

  • How long is the flight from Newfoundland and Labrador to Chicago Midway Airport?

    A quick flight from Newfoundland and Labrador to Chicago Midway Airport can take about 11h 30m. Porter Airlines provides one of the quickest options available for as low as $417. The distance between Newfoundland and Labrador and Chicago Midway Airport is about 1748 mi.

  • Can I find deals for flights from Newfoundland and Labrador to Midway that include hotel bookings?

    Yes. In addition to deals on Newfoundland and Labrador to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Newfoundland and Labrador to Midway?

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

  • Can I find deals for business class flights from Newfoundland and Labrador to Midway?

    Yes. Cheapflights offers flight deals from Newfoundland and Labrador 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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Alternative routes for Newfoundland and Labrador to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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