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Cheap flights from Newfoundland and Labrador to Chicago Midway Airport from C$ 698

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 14/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
28 Feb — 7 Mar1
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 29 January 2026.

Sat 14/26:15 a.m.
YYT
-
MDW
2 stops8h 10m
Porter Airlines
Wed 18/211:05 a.m.
MDW
-
YYT
2 stops9h 45m
Porter Airlines
Deal found 26/1C$ 698
Fri 13/34:15 p.m.
YYT
-
MDW
2 stops22h 05m
Porter Airlines
Fri 20/311:00 a.m.
MDW
-
YYT
2 stops11h 30m
Porter Airlines
Deal found 27/1C$ 926

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 29 January 2026.

Round-trip from

C$ 698
Porter Airlines
  • Porter Airlines
  • 14/2-18/2
  • 4 total stops
  • 17h 55m 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 29 January 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

Sat 14/2

6:15 a.m.-11:55 a.m.

2 stops8h 10m

Chicago Midway

Wed 18/2

11:05 a.m.-11:20 p.m.

2 stops9h 45m

C$ 698

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Fri 13/3

4:15 p.m.-11:50 a.m.

2 stops22h 05m

Chicago Midway

Fri 20/3

11:00 a.m.-1:00 a.m.

2 stops11h 30m

C$ 926

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

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 8h 10m. 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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