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Cheap flights from Newfoundland and Labrador to Chicago Midway Airport from C$ 691

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 17/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
5 Aug — 12 Aug1
1 adult

Cheap 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 31 July 2025.

Round-trip from

C$ 691
Porter Airlines
  • Porter Airlines
  • 17/9-20/9
  • 5 total stops
  • 24h 27m total
  • Newfoundland and Labrador to Chicago
Search Deals

Find 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 31 July 2025.

Wed 17/97:00 a.m.YYT - MDW
3 stops11h 54mPorter Airlines
Sat 20/99:35 a.m.MDW - YYT
2 stops12h 33mPorter Airlines
Deal found 31/7C$ 691
Wed 17/93:00 p.m.YYT - MDW
2 stops45h 10mWestJet
Sat 20/911:00 a.m.MDW - YYT
2 stops9h 26mWestJet
Deal found 31/7C$ 732

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 31 July 2025.
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

Wed 17/9

7:00 a.m.-4:24 p.m.

3 stops11h 54m

Chicago Midway

Sat 20/9

9:35 a.m.-12:38 a.m.

2 stops12h 33m

C$ 691

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 17/9

3:00 p.m.-9:40 a.m.

2 stops45h 10m

Chicago Midway

Sat 20/9

11:00 a.m.-10:56 p.m.

2 stops9h 26m

C$ 732

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/7

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 31 July 2025.
Get a feel of what it's like to fly with Porter Airlines and WestJet from Newfoundland and Labrador to Chicago Midway Airport by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • 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.

  • What is the cheapest month to book a flight from Newfoundland and Labrador to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Newfoundland and Labrador to Chicago Midway Airport (average of C$ 233). Flying from Newfoundland and Labrador to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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