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Cheap flights from Newfoundland and Labrador to Chicago from C$ 304

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 31/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
16 Jan — 23 Jan1
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 17 December 2025.

Wed 31/127:30 a.m.YYT - ORD
2 stops14h 45mAir Canada
Tue 6/13:55 p.m.ORD - YYT
1 stop7h 33mAir Canada
Deal found 16/12C$ 828

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 17 December 2025.

Round-trip from

C$ 672

One-way from

C$ 304
Air Canada
  • Air Canada
  • 29/1-31/1
  • 2 total stops
  • 15h 23m total
  • Newfoundland and Labrador to Chicago
Search Deals
31/1
  • 31/1
  • 2 total stops
  • 13h 08m 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 17 December 2025.
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

Wed 15/4

7:30 a.m.-5:45 p.m.

2 stops12h 45m

Chicago O'Hare Intl

Sat 18/4

8:40 a.m.-8:13 p.m.

2 stops9h 03m

C$ 676

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Wed 15/4

1:10 p.m.-5:45 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sat 18/4

7:55 a.m.-6:05 p.m.

2 stops7h 40m

C$ 681

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sun 1/2

5:45 a.m.-1:01 p.m.

2 stops9h 46m

Chicago O'Hare Intl

Wed 4/2

12:50 p.m.-10:52 p.m.

1 stop7h 32m

C$ 692

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 3/2

6:35 a.m.-3:10 p.m.

1 stop11h 05m

Chicago O'Hare Intl

Tue 31/3

4:15 p.m.-1:33 a.m.

1 stop6h 48m

C$ 702

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 31/12

7:30 a.m.-7:45 p.m.

2 stops14h 45m

Chicago O'Hare Intl

Tue 6/1

3:55 p.m.-1:58 a.m.

1 stop7h 33m

C$ 828

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 30/5

3:00 p.m.-4:24 p.m.

2 stops27h 54m

Chicago Midway

Wed 3/6

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

2 stops12h 18m

C$ 901

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 31/1

6:20 a.m.-4:58 p.m.

2 stops13h 08m

C$ 304

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 31/1

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

1 stop8h 31m

C$ 352

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

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 12h 45m. Air Canada provides one of the quickest options available for as low as C$ 676. The distance between Newfoundland and Labrador and Chicago is about 2816 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 St John's - Chicago O'Hare Intl, Deer Lake - 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 17 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 672AverageC$ 709FlexibilityNo 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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