Find flights
When to book
FAQs

Cheap flights from Newfoundland and Labrador to Chicago from C$ 640

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 17/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
15 oct. — 22 oct.1
1 adult
1 adult, Economy

Cheap 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 15 septiembre 2025.

Round-trip from

C$ 640
Air Canada
  • Air Canada
  • 17/12-23/12
  • 3 total stops
  • 16h 46m total
  • Newfoundland and Labrador to Chicago
Search Deals

Find flight deals from Newfoundland and Labrador to Chicago

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 15 septiembre 2025.

mié. 17/127:30 a.m.YYT - ORD
2 stops9h 55mAir Canada
mar. 23/123:35 p.m.ORD - YYT
1 stop6h 51mAir Canada
Deal found 14/9C$ 640
vie. 19/126:50 p.m.YDF - ORD
2 stops18h 58mAir Canada
mié. 24/128:15 p.m.ORD - YDF
2 stops19h 24mAir Canada
Deal found 15/9C$ 854
vie. 19/125:45 a.m.YDF - ORD
1 stop8h 03mMultiple Airlines
mié. 24/129:20 p.m.ORD - YDF
1 stop17h 13mMultiple Airlines
Deal found 15/9C$ 1,000

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 15 septiembre 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

mié. 17/12

7:30 a.m.-2:55 p.m.

2 stops9h 55m

Chicago O'Hare Intl

mar. 23/12

3:35 p.m.-12:56 a.m.

1 stop6h 51m

C$ 640

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

vie. 19/12

6:50 p.m.-11:18 a.m.

2 stops18h 58m

Chicago O'Hare Intl

mié. 24/12

8:15 p.m.-6:09 p.m.

2 stops19h 24m

C$ 854

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

vie. 19/12

5:45 a.m.-11:18 a.m.

1 stop8h 03m

Chicago O'Hare Intl

mié. 24/12

9:20 p.m.-5:03 p.m.

1 stop17h 13m

C$ 1,000

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

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 9h 55m. Air Canada provides one of the quickest options available for as low as C$ 640. The distance between Newfoundland and Labrador and Chicago is about 2816 km.

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

    While some choose either St John's - Chicago O'Hare Intl or Deer Lake - Chicago O'Hare Intl, St John's - Chicago Midway 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.

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

    Currently, January is the cheapest month in which you can book a flight from Newfoundland and Labrador to Chicago (average of C$ 261). Flying from Newfoundland and Labrador to Chicago in March is currently the most expensive (average of C$ 348). 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.

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.

Alternative routes for Newfoundland and Labrador to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Vancouver Intl to Midway flights
Calgary to O'Hare Intl flights
Québec City to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Pearson Intl to St. Louis flights
Ottawa to O'Hare Intl flights
Halifax to O'Hare Intl flights
Calgary to Midway flights
Winnipeg to O'Hare Intl flights
Québec City to Midway flights
Edmonton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Ottawa to Midway flights
Halifax to Midway flights
Victoria to O'Hare Intl flights
Edmonton to Midway flights
Vancouver Intl to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Calgary to St. Louis flights
Saskatoon to O'Hare Intl flights
Edmonton to St. Louis flights
Kelowna to O'Hare Intl flights
London to O'Hare Intl flights
Kelowna to Midway flights
Victoria to Midway flights
Hamilton to O'Hare Intl flights
Ottawa to St. Louis flights
Pearson Intl to Peoria flights
Saskatoon to Midway flights
Regina to O'Hare Intl flights
Halifax to St. Louis flights
Pearson Intl to Bloomington flights
St. John's to O'Hare Intl flights
Québec City to St. Louis flights
Kingston to O'Hare Intl flights
St John to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Moncton to O'Hare Intl flights

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 15 septiembre 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 650AverageC$ 798FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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 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.

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.