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Cheap flights from Newfoundland and Labrador to Chicago Midway Airport from C$ 402

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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
20 Apr — 27 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Newfoundland and Labrador to Midway

Enter your travel dates to find the best prices.

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 21 March 2026.

Wed 29/76:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Wed 5/83:20 p.m.
MDW
-
YYT
2 stops7h 05m
Porter Airlines
Deal found 17/3C$ 694
Tue 26/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Fri 29/53:20 p.m.
MDW
-
YYT
2 stops7h 06m
Porter Airlines
Deal found 18/3C$ 726
Sat 18/46:00 a.m.
YYT
-
MDW
2 stops8h 40m
Porter Airlines
Wed 22/411:00 a.m.
MDW
-
YYT
2 stops9h 35m
Porter Airlines
Deal found 20/3C$ 752
Fri 22/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Mon 1/63:20 p.m.
MDW
-
YYT
2 stops7h 06m
Porter Airlines
Deal found 18/3C$ 913
Wed 29/74:00 p.m.
YYT
-
MDW
3 stops20h 10m
Multiple Airlines
Wed 5/81:00 p.m.
MDW
-
YYT
3 stops9h 25m
Multiple Airlines
Deal found 17/3C$ 1,383
Sat 28/33:00 p.m.
YYT
-
MDW
2 stops24h 55m
WestJet
Tue 31/37:20 p.m.
MDW
-
YYT
2 stops49h 08m
WestJet
Deal found 19/3C$ 1,559

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 21 March 2026.

Round-trip from

C$ 694

One-way from

C$ 402
Porter Airlines
  • Porter Airlines
  • 29/7-5/8
  • 4 total stops
  • 18h 05m total
  • Newfoundland and Labrador to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 7/7
  • 2 total stops
  • 11h 00m total
  • Newfoundland and Labrador to Chicago
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 629,999 searches. Data last updated 21 March 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

6:05 a.m.-2:35 p.m.

2 stops11h 00m

Chicago Midway

Fri 29/5

3:20 p.m.-12:56 a.m.

2 stops7h 06m

C$ 726

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 18/4

6:00 a.m.-12:10 p.m.

2 stops8h 40m

Chicago Midway

Wed 22/4

11:00 a.m.-11:05 p.m.

2 stops9h 35m

C$ 752

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 22/5

6:05 a.m.-2:35 p.m.

2 stops11h 00m

Chicago Midway

Mon 1/6

3:20 p.m.-12:56 a.m.

2 stops7h 06m

C$ 913

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 29/7

4:00 p.m.-9:40 a.m.

3 stops20h 10m

Chicago Midway

Wed 5/8

1:00 p.m.-12:55 a.m.

3 stops9h 25m

C$ 1,383
Cheapest one-way
Quickest one-way

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 7/7

6:05 a.m.-2:35 p.m.

2 stops11h 00m

C$ 402

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 7/7

6:05 a.m.-6:31 p.m.

3 stops14h 56m

C$ 615

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Sorted by cheapest first

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?

    There are many flights that can get you from Newfoundland and Labrador to Chicago Midway Airport in 11h. Fly via Porter Airlines to get the fastest option. The distance between Newfoundland and Labrador and Chicago Midway Airport is about 2813 km.

  • 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.

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Can Cheapflights find flights from Newfoundland and Labrador to Midway with no change fees?

Yes, we can. To see specific flights from Newfoundland and Labrador to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Newfoundland and Labrador to Midway become cheaper?

Not ready to book yet? You can track prices for flights from Newfoundland and Labrador to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.

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