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Cheap flights from Newfoundland and Labrador to Chicago from C$ 302

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
5 Aug — 12 Aug1
1 adult

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 31 July 2025.

Round-trip from

C$ 642

One-way from

C$ 302
Air Canada
  • Air Canada
  • 9/9-12/9
  • 2 total stops
  • 12h 30m total
  • Newfoundland and Labrador to Chicago
Search Deals
Air Canada
  • Air Canada
  • 15/9
  • 1 total stop
  • 6h 31m 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 31 July 2025.

Tue 9/95:50 a.m.YYT - ORD
1 stop6h 31mAir Canada
Fri 12/98:40 a.m.ORD - YYT
1 stop5h 59mAir Canada
Deal found 31/7C$ 642
Wed 17/97:00 a.m.YYT - MDW
3 stops11h 54mPorter Airlines
Sat 20/99:35 a.m.MDW - YYT
2 stops12h 33mPorter Airlines
Deal found 31/7C$ 691
Wed 17/93:00 p.m.YYT - ORD
2 stops30h 16mWestJet
Sat 20/96:20 p.m.ORD - YYT
2 stops26h 06mWestJet
Deal found 31/7C$ 703
Sun 14/96:00 a.m.YYT - ORD
2 stops15h 20mMultiple Airlines
Sun 21/95:17 p.m.ORD - YYT
1 stop18h 43mMultiple Airlines
Deal found 31/7C$ 718
Wed 17/93:00 p.m.YYT - MDW
2 stops45h 10mWestJet
Sat 20/911:00 a.m.MDW - YYT
2 stops9h 26mWestJet
Deal found 31/7C$ 732
Tue 9/95:50 a.m.YYT - ORD
1 stop6h 31mUnited Airlines
Fri 12/99:00 a.m.ORD - YYT
2 stops13h 09mUnited Airlines
Deal found 31/7C$ 736

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 31 July 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

Tue 9/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

Chicago O'Hare Intl

Fri 12/9

8:40 a.m.-5:09 p.m.

1 stop5h 59m

C$ 642

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 17/9

7:00 a.m.-4:24 p.m.

3 stops11h 54m

Chicago Midway

Sat 20/9

9:35 a.m.-12:38 a.m.

2 stops12h 33m

C$ 691

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Fri 22/8

6:10 a.m.-9:52 a.m.

1 stop6h 12m

Chicago O'Hare Intl

Mon 25/8

3:35 p.m.-11:35 p.m.

1 stop5h 30m

C$ 693

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 17/9

3:00 p.m.-6:46 p.m.

2 stops30h 16m

Chicago O'Hare Intl

Sat 20/9

6:20 p.m.-10:56 p.m.

2 stops26h 06m

C$ 703

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 14/9

6:00 a.m.-6:50 p.m.

2 stops15h 20m

Chicago O'Hare Intl

Sun 21/9

5:17 p.m.-2:30 p.m.

1 stop18h 43m

C$ 718

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 17/9

3:00 p.m.-9:40 a.m.

2 stops45h 10m

Chicago Midway

Sat 20/9

11:00 a.m.-10:56 p.m.

2 stops9h 26m

C$ 732

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 9/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

Chicago O'Hare Intl

Fri 12/9

9:00 a.m.-12:39 a.m.

2 stops13h 09m

C$ 736

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Fri 22/8

6:10 a.m.-7:14 p.m.

2 stops15h 34m

Chicago O'Hare Intl

Mon 25/8

3:35 p.m.-11:35 p.m.

1 stop5h 30m

C$ 796

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Fri 22/8

6:10 a.m.-2:13 p.m.

2 stops10h 33m

Chicago O'Hare Intl

Mon 25/8

9:55 a.m.-11:35 p.m.

2 stops11h 10m

C$ 805

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 15/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

C$ 302

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/7

Showing 1-10 of 14 results
1
2

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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 31 July 2025.
Get a feel of what it's like to fly with Porter Airlines,United Airlines, andWestJet from Newfoundland and Labrador to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Crew

8.7

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Crew

8.7

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Crew

8.7

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Crew

8.7

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,851 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Crew

8.7

Food

7.6

Overall

8.0

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • 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.

  • 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$ 352). 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

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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 31 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 636AverageC$ 759FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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

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

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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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