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Cheap flights from Chicago to Newfoundland and Labrador from C$ 360

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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
16 Apr — 23 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Newfoundland and Labrador

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Newfoundland and Labrador
Explore the most affordable flight options available from Chicago to Newfoundland and Labrador. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 March 2026.

Mon 4/53:20 p.m.
MDW
-
YYT
2 stops7h 06m
Multiple Airlines
Mon 11/56:00 a.m.
YYT
-
MDW
1 stop11h 05m
Multiple Airlines
Deal found 15/3C$ 589
Thu 23/411:00 a.m.
MDW
-
YYT
2 stops11h 31m
Multiple Airlines
Fri 1/51:20 p.m.
YYT
-
MDW
1 stop22h 50m
Multiple Airlines
Deal found 17/3C$ 611
Thu 23/411:00 a.m.
MDW
-
YYT
2 stops11h 31m
Multiple Airlines
Sat 2/53:00 p.m.
YYT
-
MDW
1 stop26h 05m
Multiple Airlines
Deal found 17/3C$ 630
Thu 23/411:00 a.m.
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Fri 1/56:55 p.m.
YYT
-
MDW
1 stop17h 15m
Porter Airlines
Deal found 17/3C$ 637
Fri 24/44:05 p.m.
MDW
-
YYT
1 stop28h 23m
Multiple Airlines
Fri 1/56:05 a.m.
YYT
-
MDW
2 stops33h 25m
Multiple Airlines
Deal found 17/3C$ 664
Fri 24/44:05 p.m.
MDW
-
YYT
2 stops30h 26m
Multiple Airlines
Sat 2/53:00 p.m.
YYT
-
MDW
1 stop26h 05m
Multiple Airlines
Deal found 17/3C$ 668
Fri 17/47:55 a.m.
ORD
-
YYT
2 stops14h 36m
Multiple Airlines
Tue 21/46:20 a.m.
YYT
-
ORD
2 stops15h 35m
Multiple Airlines
Deal found 12/3C$ 715
Wed 29/411:00 a.m.
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Wed 6/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 14/3C$ 716
Fri 17/47:55 a.m.
ORD
-
YYT
2 stops13h 03m
Air Canada
Tue 21/46:35 a.m.
YYT
-
ORD
1 stop9h 00m
Air Canada
Deal found 12/3C$ 734
Thu 3/911:45 a.m.
ORD
-
YYT
2 stops10h 40m
Porter Airlines
Sun 13/91:45 p.m.
YYT
-
ORD
2 stops10h 20m
Porter Airlines
Deal found 12/3C$ 771
Fri 4/93:20 p.m.
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sun 13/96:05 a.m.
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 13/3C$ 812
Tue 2/63:45 p.m.
ORD
-
YYT
1 stop7h 33m
Air Canada
Wed 3/65:35 a.m.
YYT
-
ORD
2 stops10h 05m
Air Canada
Deal found 12/3C$ 822

Find flight deals from Chicago to Newfoundland and Labrador

Keep the following information in mind while searching for Chicago to Newfoundland and Labrador flight deals. Data was last updated 17 March 2026.

Round-trip from

C$ 589

One-way from

C$ 360
4/5-11/5
  • 4/5-11/5
  • 3 total stops
  • 18h 11m total
  • Chicago to Newfoundland and Labrador
Search Deals
Porter Airlines
  • Porter Airlines
  • 10/6
  • 2 total stops
  • 12h 01m total
  • Chicago to Newfoundland and Labrador
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Newfoundland and Labrador 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 March 2026.
Use the filters below to find and compare flights from Chicago to Newfoundland and Labrador that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Mon 4/5

3:20 p.m.-12:56 a.m.

2 stops7h 06m

St John's

Mon 11/5

6:00 a.m.-2:35 p.m.

1 stop11h 05m

C$ 589

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 24/4

4:05 p.m.-10:58 p.m.

1 stop28h 23m

St John's

Sat 2/5

3:00 p.m.-2:35 p.m.

1 stop26h 05m

C$ 676

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 29/4

11:00 a.m.-1:01 a.m.

2 stops11h 31m

St John's

Wed 6/5

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

2 stops11h 00m

C$ 716

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 13/6

10:25 a.m.-12:56 a.m.

2 stops12h 01m

St John's

Mon 22/6

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

2 stops11h 00m

C$ 780

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 26/8

3:20 p.m.-12:55 a.m.

2 stops7h 05m

St John's

Sun 30/8

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

2 stops11h 00m

C$ 789

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 1/7

10:25 a.m.-12:55 a.m.

2 stops12h 00m

St John's

Fri 31/7

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

2 stops11h 00m

C$ 794

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Mon 20/7

3:20 p.m.-12:55 a.m.

2 stops7h 05m

St John's

Tue 28/7

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

2 stops11h 00m

C$ 812
Quickest round-trip

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 13/5

8:45 a.m.-7:43 p.m.

2 stops8h 28m

St John's

Sat 16/5

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

1 stop7h 13m

C$ 863

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 30/6

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

2 stops12h 13m

St John's

Tue 7/7

5:35 a.m.-10:16 a.m.

1 stop7h 11m

C$ 863

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 26/8

8:45 a.m.-7:43 p.m.

2 stops8h 28m

St John's

Sun 30/8

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

2 stops10h 05m

C$ 890

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/3

Showing 1-10 of 23 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Newfoundland and Labrador

Have a flexible travel schedule? Discover the best time to fly to Newfoundland and Labrador from Chicago 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 Chicago to Newfoundland and Labrador
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 Chicago to Newfoundland and Labrador. 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 Chicago to Newfoundland and Labrador?

    Airlines like Porter Airlines and Air Canada fly from Chicago to Newfoundland and Labrador in about 8h 28m. The time it takes to get you to your destination can typically vary by up to 3h 33m. There are 2816 km between Chicago and Newfoundland and Labrador. Both multi-stop and direct flights can be found to your destination and back.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Newfoundland and Labrador.

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

    Yes. Cheapflights offers flight deals from Chicago to Newfoundland and Labrador 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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Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Chicago to Newfoundland and Labrador. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Newfoundland and Labrador.

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

Yes! Cheapflights helps users easily find flights from Chicago to Newfoundland and Labrador with no change fees.

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

Yes, Cheapflights offers price alerts on Chicago to Newfoundland and Labrador flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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