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Newfoundland and Labrador

$290+ Cheap flights from Chicago (CHI) to Newfoundland and Labrador

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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
Jul 16 — Jul 231
Thu 7/16
Thu 7/23
1 adult, Economy
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Cheap flight deals from Chicago to Newfoundland and Labrador

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 June 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sat 10/107:00 pm
YYT
-
ORD
1 stop18h 30m
Porter Airlines
Deal found 6/12$530
This FlightHub deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/63:20 pm
MDW
-
YYT
2 stops7h 05m
Porter Airlines
Thu 7/96:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 6/13$610
This Gotogate deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:15 pm
MDW
-
YYT
2 stops7h 10m
Porter Airlines
Mon 8/316:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 6/15$627
This Gotogate deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/23:15 pm
MDW
-
YYT
2 stops7h 10m
Porter Airlines
Sun 8/96:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 6/16$629
This oojo deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:45 am
ORD
-
YYT
1 stop9h 40m
Porter Airlines
Tue 8/2510:00 am
YYT
-
ORD
1 stop8h 49m
Porter Airlines
Deal found 6/14$644
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:20 am
MDW
-
YYT
1 stop10h 05m
Multiple Airlines
Mon 8/316:00 am
YYT
-
MDW
2 stops11h 05m
Multiple Airlines
Deal found 6/15$648
This Porter Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:45 am
ORD
-
YYT
2 stops10h 40m
Porter Airlines
Fri 9/186:00 am
YYT
-
ORD
2 stops11h 05m
Porter Airlines
Deal found 6/13$662
This Trip.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:25 am
MDW
-
YYT
1 stop11h 13m
Porter Airlines
Sun 7/196:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 6/16$669
This Air Canada deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:09 am
ORD
-
YDF
2 stops8h 41m
Air Canada
Sun 9/272:05 pm
YDF
-
ORD
1 stop8h 13m
Air Canada
Deal found 6/15$684
This Air Canada deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:45 pm
ORD
-
YDF
1 stop6h 43m
Air Canada
Sun 10/45:25 am
YDF
-
ORD
2 stops11h 57m
Air Canada
Deal found 6/16$687
This Mytrip deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/313:20 pm
MDW
-
YYT
2 stops7h 05m
Porter Airlines
Fri 8/76:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 6/16$689
This oojo deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:20 am
MDW
-
YYT
2 stops10h 05m
Porter Airlines
Sun 8/306:00 am
YYT
-
MDW
2 stops30h 10m
Porter Airlines
Deal found 6/15$690

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 June 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$530
(Kiwi.com)

One-way from

$290
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-St John's flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-St John's flights.
Search Deals
From Chicago (CHI) to Newfoundland and Labrador
Search Deals
One-way flight from Chicago (CHI) 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 2,558,603 searches. Data last updated June 16, 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

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 8/4

8:45 am-5:10 pm

1 stop5h 55m

St John's

Sat 8/8

5:00 am-1:22 pm

1 stop10h 52m

$597

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Mon 7/6

3:20 pm-12:55 am

2 stops7h 05m

St John's

Thu 7/9

6:05 am-2:35 pm

2 stops11h 00m

$610

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 8/28

3:15 pm-12:55 am

2 stops7h 10m

St John's

Mon 8/31

6:05 am-2:35 pm

2 stops11h 00m

$627

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 8/28

10:20 am-10:55 pm

1 stop10h 05m

St John's

Mon 8/31

6:00 am-2:35 pm

2 stops11h 05m

$648

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 9/16

11:45 am-12:55 am

2 stops10h 40m

St John's

Fri 9/18

6:00 am-2:35 pm

2 stops11h 05m

$662

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sun 7/26

2:15 pm-11:21 pm

1 stop6h 36m

St John's

Wed 7/29

8:30 am-2:55 pm

1 stop8h 55m

$683

ChicagoDeer Lake

ORD - YDF

ORDYDF

Chicago O'Hare Intl

Fri 10/16

2:15 pm-12:58 am

1 stop8h 13m

Deer Lake

Sat 10/17

2:05 pm-7:48 pm

1 stop8h 13m

$684
Quickest round-trip

ChicagoDeer Lake

ORD - YDF

ORDYDF

Chicago O'Hare Intl

Thu 9/24

3:45 pm-12:58 am

1 stop6h 43m

Deer Lake

Sun 9/27

2:05 pm-7:48 pm

1 stop8h 13m

$684

ChicagoDeer Lake

ORD - YDF

ORDYDF

Chicago O'Hare Intl

Fri 9/25

3:45 pm-12:58 am

1 stop6h 43m

Deer Lake

Sun 10/4

2:05 pm-7:48 pm

1 stop8h 13m

$684

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 8/26

3:45 pm-1:46 am

1 stop7h 31m

St John's

Sun 8/30

8:30 am-2:55 pm

1 stop8h 55m

$685

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 26 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.

Reviews of airlines servicing Newfoundland and Labrador

Get insights into the airlines that provide service to Newfoundland and Labrador. 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 Newfoundland and Labrador. Reviews last updated June 16, 2026.
Peruse reviews from past customers who have flown with Air Canada from Chicago to Newfoundland and Labrador to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
11,197 reviews

Boarding

7.3

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

Comfort

7.1

Reviews

1 / 20
8.0
Excellent

Dr vandana,Feb 2026

SFO - YYC

It was good, the lounge facilities can be better with some vegetarian options. Overall good
Air Canada
7.1
Good
11,197 reviews
Air Canada
7.1
Good
11,197 reviews

Boarding

7.3

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

Comfort

7.1

Reviews

1 / 20
8.0
Excellent

Dr vandana,Feb 2026

SFO - YYC

It was good, the lounge facilities can be better with some vegetarian options. Overall good

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?

    Air Canada and Porter Airlines can get you from Chicago to Newfoundland and Labrador in just under 5h 55m. Your travel time can differ by up to 1h 10m. The distance between Chicago and Newfoundland and Labrador is about 1750 mi. This flight may include one or multiple stops.

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

    When deciding which route to take from Chicago to Newfoundland and Labrador consider Chicago O'Hare Intl - St John's, Chicago Midway - St John's or Chicago O'Hare Intl - Deer Lake as they are the most popular.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Chicago to Newfoundland and Labrador

Discover the top 2 airlines that operate flights from Chicago to Newfoundland and Labrador. 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 2,558,603 searches. Data last updated June 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$527Average$669FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$614Average$786FlexibilityNo cancel feeOn-time69%

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