Find flights
When to book
FAQs

Cheap flights from Newfoundland and Labrador to Chicago Midway Airport from C$ 428

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — MDW
18 Jul — 25 Jul1
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 18 June 2026.

Tue 11/86:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Sun 30/83:15 p.m.
MDW
-
YYT
2 stops7h 10m
Porter Airlines
Deal found 16/6C$ 762
Thu 6/86:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Thu 20/810:20 a.m.
MDW
-
YYT
2 stops12h 05m
Porter Airlines
Deal found 17/6C$ 777
Thu 2/710:00 a.m.
YYT
-
MDW
1 stop26h 10m
Porter Airlines
Sat 11/710:25 a.m.
MDW
-
YYT
2 stops34h 00m
Porter Airlines
Deal found 14/6C$ 780
Thu 30/76:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Thu 6/83:15 p.m.
MDW
-
YYT
2 stops7h 10m
Porter Airlines
Deal found 15/6C$ 786
Thu 30/74:00 p.m.
YYT
-
MDW
3 stops20h 10m
Multiple Airlines
Thu 6/810:20 a.m.
MDW
-
YYT
2 stops12h 05m
Multiple Airlines
Deal found 15/6C$ 1,061
Thu 6/86:05 a.m.
YYT
-
MDW
2 stops11h 00m
Multiple Airlines
Thu 20/89:59 a.m.
MDW
-
YYT
3 stops24h 06m
Multiple Airlines
Deal found 17/6C$ 1,086
Sat 1/86:05 a.m.
YYT
-
MDW
2 stops30h 05m
Porter Airlines
Sat 8/810:20 a.m.
MDW
-
YYT
2 stops12h 05m
Porter Airlines
Deal found 17/6C$ 1,098

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 18 June 2026.

Round-trip from

C$ 762

One-way from

C$ 428
Porter Airlines
  • Porter Airlines
  • 11/8-30/8
  • 4 total stops
  • 18h 10m total
  • Newfoundland and Labrador to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 9/8
  • 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 18 June 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 11/8

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

2 stops11h 00m

Chicago Midway

Sun 30/8

3:15 p.m.-12:55 a.m.

2 stops7h 10m

C$ 762

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 2/7

10:00 a.m.-9:40 a.m.

1 stop26h 10m

Chicago Midway

Sat 11/7

10:25 a.m.-10:55 p.m.

2 stops34h 00m

C$ 780

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 30/7

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

2 stops11h 00m

Chicago Midway

Thu 6/8

3:15 p.m.-12:55 a.m.

2 stops7h 10m

C$ 786

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 30/7

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

3 stops20h 10m

Chicago Midway

Thu 6/8

10:20 a.m.-12:55 a.m.

2 stops12h 05m

C$ 1,061

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 6/8

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

2 stops11h 00m

Chicago Midway

Thu 20/8

9:59 a.m.-12:35 p.m.

3 stops24h 06m

C$ 1,086

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/8

6:05 a.m.-9:40 a.m.

2 stops30h 05m

Chicago Midway

Sat 8/8

10:20 a.m.-12:55 a.m.

2 stops12h 05m

C$ 1,098

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 1/8

6:05 a.m.-9:13 a.m.

3 stops29h 38m

Chicago Midway

Sat 8/8

1:27 p.m.-3:05 p.m.

3 stops23h 08m

C$ 1,664
Cheapest one-way
Quickest one-way

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 9/8

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

2 stops11h 00m

C$ 428

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Mon 14/9

3:00 p.m.-9:53 a.m.

2 stops21h 23m

C$ 568

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Mon 14/9

7:00 p.m.-10:58 a.m.

3 stops42h 28m

C$ 600

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/6

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

Why should you use Cheapflights to find cheap flight tickets from Newfoundland and Labrador to Midway?

Millions of users choose and trust Cheapflights to book the best flight deals from Newfoundland and Labrador to Midway for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.