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Cheap flights from Newfoundland and Labrador to Chicago from C$ 353

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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
31 May — 7 Jun1
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 1 May 2026.

Sat 26/92:05 p.m.
YDF
-
ORD
1 stop8h 13m
Air Canada
Wed 30/98:45 a.m.
ORD
-
YDF
1 stop5h 19m
Air Canada
Deal found 29/4C$ 673
Tue 24/115:05 a.m.
YYT
-
ORD
1 stop8h 35m
Air Canada
Sat 28/113:55 p.m.
ORD
-
YYT
1 stop6h 31m
Air Canada
Deal found 26/4C$ 677
Tue 12/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Tue 19/510:30 a.m.
MDW
-
YYT
2 stops11h 55m
Porter Airlines
Deal found 26/4C$ 681
Mon 31/85:35 a.m.
YYT
-
ORD
2 stops10h 05m
Air Canada
Thu 3/98:45 a.m.
ORD
-
YYT
2 stops12h 13m
Air Canada
Deal found 29/4C$ 715
Fri 12/65:00 a.m.
YDF
-
ORD
1 stop6h 30m
Air Canada
Mon 15/69:55 a.m.
ORD
-
YDF
1 stop13h 34m
Air Canada
Deal found 27/4C$ 733
Tue 26/55:35 a.m.
YYT
-
ORD
2 stops10h 20m
Air Canada
Tue 2/68:20 p.m.
ORD
-
YYT
2 stops14h 28m
Air Canada
Deal found 29/4C$ 769
Tue 26/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Tue 2/610:15 a.m.
MDW
-
YYT
2 stops12h 11m
Porter Airlines
Deal found 26/4C$ 769
Sat 26/92:05 p.m.
YDF
-
ORD
2 stops11h 40m
United Airlines
Wed 30/95:00 a.m.
ORD
-
YDF
2 stops9h 04m
United Airlines
Deal found 29/4C$ 775
Sat 13/65:35 a.m.
YYT
-
ORD
1 stop7h 13m
Air Canada
Sat 20/63:45 p.m.
ORD
-
YYT
1 stop7h 31m
Air Canada
Deal found 29/4C$ 787
Tue 26/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Multiple Airlines
Tue 2/67:13 p.m.
MDW
-
YYT
3 stops27h 13m
Multiple Airlines
Deal found 26/4C$ 876
Tue 15/93:00 p.m.
YYT
-
MDW
2 stops24h 41m
Delta
Sat 19/95:59 p.m.
MDW
-
YYT
2 stops26h 26m
Delta
Deal found 28/4C$ 1,146

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 1 May 2026.

Round-trip from

C$ 673

One-way from

C$ 353
Air Canada
  • Air Canada
  • 26/9-30/9
  • 2 total stops
  • 13h 32m total
  • Newfoundland and Labrador to Chicago
Search Deals
Air Canada
  • Air Canada
  • 4/7
  • 1 total stop
  • 6h 30m 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 1 May 2026.
Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

8:45 a.m.-11:28 p.m.

2 stops12h 13m

C$ 718
Quickest round-trip

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sun 14/6

5:00 a.m.-9:00 a.m.

1 stop6h 30m

Chicago O'Hare Intl

Sun 21/6

8:35 a.m.-4:35 p.m.

1 stop5h 30m

C$ 765

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Fri 12/6

7:00 p.m.-10:18 a.m.

2 stops17h 48m

Chicago O'Hare Intl

Mon 15/6

9:55 a.m.-1:59 a.m.

1 stop13h 34m

C$ 765

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

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

2 stops11h 00m

Chicago Midway

Tue 2/6

10:15 a.m.-12:56 a.m.

2 stops12h 11m

C$ 769

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 26/5

5:35 a.m.-1:25 p.m.

2 stops10h 20m

Chicago O'Hare Intl

Tue 2/6

8:20 p.m.-1:18 p.m.

2 stops14h 28m

C$ 769

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sat 26/9

2:05 p.m.-11:15 p.m.

2 stops11h 40m

Chicago O'Hare Intl

Wed 30/9

5:00 a.m.-4:34 p.m.

2 stops9h 04m

C$ 775

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sat 26/9

5:25 a.m.-6:33 p.m.

2 stops15h 38m

Chicago O'Hare Intl

Wed 30/9

7:09 a.m.-6:20 p.m.

2 stops8h 41m

C$ 835

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 13/6

5:35 a.m.-10:18 a.m.

1 stop7h 13m

Chicago O'Hare Intl

Sat 20/6

11:03 a.m.-12:45 a.m.

2 stops11h 12m

C$ 847

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sun 14/6

5:00 a.m.-11:26 p.m.

2 stops20h 56m

Chicago O'Hare Intl

Sun 21/6

6:00 a.m.-4:35 p.m.

2 stops8h 05m

C$ 866

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 26/5

5:40 p.m.-10:05 p.m.

1 stop6h 55m

Chicago O'Hare Intl

Tue 2/6

7:40 p.m.-1:01 p.m.

2 stops14h 51m

C$ 874

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/4

Showing 1-10 of 31 resultsSorted by cheapest first
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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 13m. Air Canada provides one of the quickest options available for as low as C$ 675. The distance between Newfoundland and Labrador and Chicago is about 2485 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 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.

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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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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