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Cheap flights from Newfoundland and Labrador to Chicago from C$ 341

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 13/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
28 Feb — 7 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Newfoundland and Labrador to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Newfoundland and Labrador to Chicago
Explore the most affordable flight options available from Newfoundland and Labrador to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 January 2026.

Sat 14/25:05 a.m.
YYT
-
ORD
1 stop8h 31m
Air Canada
Wed 18/27:15 a.m.
ORD
-
YYT
1 stop7h 36m
Air Canada
Deal found 26/1C$ 696
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
Tue 27/106:00 a.m.
YDF
-
ORD
2 stops9h 40m
Air Canada
Sat 31/1012:50 p.m.
ORD
-
YDF
1 stop7h 52m
Air Canada
Deal found 28/1C$ 725
Fri 13/36:35 a.m.
YYT
-
ORD
1 stop8h 56m
Air Canada
Fri 20/38:40 p.m.
ORD
-
YYT
1 stop13h 28m
Air Canada
Deal found 27/1C$ 734
Sat 14/25:05 a.m.
YYT
-
ORD
2 stops12h 03m
United Airlines
Wed 18/26:00 a.m.
ORD
-
YYT
2 stops8h 44m
United Airlines
Deal found 27/1C$ 785
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
Fri 13/36:20 a.m.
YYT
-
ORD
3 stops20h 17m
Multiple Airlines
Fri 20/38:41 p.m.
ORD
-
YYT
3 stops25h 49m
Multiple Airlines
Deal found 27/1C$ 1,166
Fri 13/34:15 p.m.
YYT
-
ORD
2 stops22h 50m
Porter Airlines
Fri 20/39:46 a.m.
ORD
-
YYT
2 stops27h 19m
Porter Airlines
Deal found 27/1C$ 1,296

Find flight deals from Newfoundland and Labrador to Chicago

Keep the following information in mind while searching for Newfoundland and Labrador to Chicago flight deals. Data was last updated 29 January 2026.

Round-trip from

C$ 696

One-way from

C$ 341
Air Canada
  • Air Canada
  • 14/2-18/2
  • 2 total stops
  • 16h 07m total
  • Newfoundland and Labrador to Chicago
Search Deals
Air Canada
  • Air Canada
  • 13/3
  • 1 total stop
  • 8h 56m total
  • Newfoundland and Labrador to Chicago
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Newfoundland and Labrador to Chicago 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 that are best for you.

Fly from

Newfoundland and Labrador

Fly to

Chicago

Route

Depart

Return

Price

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 14/2

5:05 a.m.-11:06 a.m.

1 stop8h 31m

Chicago O'Hare Intl

Wed 18/2

7:15 a.m.-5:21 p.m.

1 stop7h 36m

C$ 696

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 - ORD

YYTORD

St John's

Fri 13/3

6:35 a.m.-1:01 p.m.

1 stop8h 56m

Chicago O'Hare Intl

Fri 20/3

8:40 p.m.-12:38 p.m.

1 stop13h 28m

C$ 734

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 14/2

5:05 a.m.-2:38 p.m.

2 stops12h 03m

Chicago O'Hare Intl

Wed 18/2

6:00 a.m.-5:14 p.m.

2 stops8h 44m

C$ 785

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

St. John'sChicago

YYT - ORD

YYTORD

St John's

Fri 13/3

6:20 a.m.-12:07 a.m.

3 stops20h 17m

Chicago O'Hare Intl

Fri 20/3

8:41 p.m.-1:00 a.m.

3 stops25h 49m

C$ 1,166

St. John'sChicago

YYT - ORD

YYTORD

St John's

Fri 13/3

6:35 a.m.-1:01 p.m.

1 stop8h 56m

C$ 341

St. John'sChicago

YYT - ORD

YYTORD

St John's

Fri 13/3

6:20 a.m.-12:07 a.m.

3 stops20h 17m

C$ 452

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Best time to book a flight from Newfoundland and Labrador to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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
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 Chicago. 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?

    A quick flight from Newfoundland and Labrador to Chicago can take about 8h 10m. Air Canada provides one of the quickest options available for as low as C$ 698. The distance between Newfoundland and Labrador and Chicago is about 2813 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most popular routes from Newfoundland and Labrador to Chicago?

    While some choose either St John's - Chicago Midway or Deer Lake - Chicago O'Hare Intl, St John's - Chicago O'Hare Intl is the most popular route from Newfoundland and Labrador to Chicago.

  • Can I find deals for flights from Newfoundland and Labrador to Chicago that include hotel bookings?

    Yes. In addition to deals on Newfoundland and Labrador to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Newfoundland and Labrador to Chicago?

    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 Chicago.

  • Can I find deals for business class flights from Newfoundland and Labrador to Chicago?

    Yes. Cheapflights offers flight deals from Newfoundland and Labrador to Chicago 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 Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Newfoundland and Labrador to Chicago

Discover the top airline that operate flights from Newfoundland and Labrador to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 29 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 663AverageC$ 700FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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

When you search for this flight from Newfoundland and Labrador to Chicago, 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 Chicago?

Cheapflights simply makes it quick and affordable to book flights from Newfoundland and Labrador to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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

Certainly. Search results for flights to Chicago from Newfoundland and Labrador shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Newfoundland and Labrador today and book when prices fit your budget.

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