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Cheap flights from Newfoundland and Labrador to Chicago Midway Airport from C$ 390

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 24/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
11 Jan — 18 Jan1
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.

Best flights from Newfoundland and Labrador to Midway
Discover carefully curated flight deals from Newfoundland and Labrador to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 December 2025.

Wed 15/46:00 a.m.YYT - MDW
2 stops11h 50mPorter Airlines
Sat 18/412:45 p.m.MDW - YYT
2 stops7h 50mPorter Airlines
Deal found 10/12C$ 730
Sat 30/51:10 p.m.YYT - MDW
2 stops29h 44mPorter Airlines
Wed 3/69:40 a.m.MDW - YYT
2 stops12h 18mPorter Airlines
Deal found 9/12C$ 903
Sat 24/16:00 a.m.YYT - MDW
2 stops30h 35mPorter Airlines
Sat 31/112:45 p.m.MDW - YYT
2 stops8h 00mPorter Airlines
Deal found 10/12C$ 1,168

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 12 December 2025.

Round-trip from

C$ 730

One-way from

C$ 390
Porter Airlines
  • Porter Airlines
  • 15/4-18/4
  • 4 total stops
  • 19h 40m total
  • Newfoundland and Labrador to Chicago
Search Deals
24/1
  • 24/1
  • 3 total stops
  • 31h 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 12 December 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 15/4

6:00 a.m.-3:20 p.m.

2 stops11h 50m

Chicago Midway

Sat 18/4

12:45 p.m.-11:05 p.m.

2 stops7h 50m

C$ 730

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 30/5

1:10 p.m.-4:24 p.m.

2 stops29h 44m

Chicago Midway

Wed 3/6

9:40 a.m.-12:28 a.m.

2 stops12h 18m

C$ 903

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 24/1

6:00 a.m.-10:05 a.m.

2 stops30h 35m

Chicago Midway

Sat 31/1

12:45 p.m.-11:15 p.m.

2 stops8h 00m

C$ 1,168

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 24/1

6:20 a.m.-11:45 a.m.

3 stops31h 55m

C$ 390

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 24/1

6:20 a.m.-11:50 a.m.

2 stops8h 00m

C$ 538

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

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 50m. 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.

See more FAQs

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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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How does Cheapflights help users find flights from Newfoundland and Labrador to Midway?

When you search for this flight from Newfoundland and Labrador to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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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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