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Newfoundland and Labrador

$295+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
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 May 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Thu 6/410:15 am
MDW
-
YYT
2 stops12h 11m
Multiple Airlines
Wed 6/101:20 pm
YYT
-
MDW
1 stop22h 45m
Multiple Airlines
Deal found 5/1$487
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 6/1210:15 am
MDW
-
YYT
1 stop11h 50m
Multiple Airlines
Mon 6/153:00 pm
YYT
-
MDW
1 stop21h 05m
Multiple Airlines
Deal found 5/3$497
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/310:15 am
MDW
-
YYT
2 stops36h 11m
Multiple Airlines
Wed 6/243:00 pm
YYT
-
MDW
1 stop21h 10m
Multiple Airlines
Deal found 5/5$523
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Tue 6/2310:25 am
MDW
-
YYT
1 stop23h 40m
Multiple Airlines
Sun 6/286:00 am
YYT
-
MDW
2 stops30h 10m
Multiple Airlines
Deal found 5/2$540
This Mytrip deal was found by Cheapflights users on 5/1. 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.
Thu 6/47:25 am
ORD
-
YYT
2 stops15h 01m
Multiple Airlines
Wed 6/106:05 am
YYT
-
ORD
2 stops16h 41m
Multiple Airlines
Deal found 5/1$552
This Mytrip deal was found by Cheapflights users on 5/3. 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.
Mon 6/810:15 am
MDW
-
YYT
2 stops12h 11m
Porter Airlines
Mon 6/156:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 5/3$553
This Mytrip deal was found by Cheapflights users on 5/1. 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.
Thu 6/42:00 pm
ORD
-
YYT
1 stop9h 18m
Air Canada
Wed 6/106:10 pm
YYT
-
ORD
2 stops17h 20m
Air Canada
Deal found 5/1$567
This Gotogate deal was found by Cheapflights users on 5/2. 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.
Sat 10/1711:45 am
ORD
-
YYT
2 stops10h 40m
Porter Airlines
Sat 10/246:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 5/2$575
This Mytrip deal was found by Cheapflights users on 5/5. 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.
Sun 10/183:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Fri 10/236:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 5/5$576
This Porter Airlines deal was found by Cheapflights users on 5/3. 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.
Fri 6/510:15 am
MDW
-
YYT
2 stops12h 11m
Porter Airlines
Mon 6/86:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 5/3$582
This FlightHub deal was found by Cheapflights users on 5/1. 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 5/1$587
This FlightHub deal was found by Cheapflights users on 5/1. 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.
Wed 9/303:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sat 10/106:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 5/1$594

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 May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$487
(Kiwi.com)

One-way from

$295
(Air Canada)
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 May 5, 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

Thu 6/4

10:15 am-12:56 am

2 stops12h 11m

St John's

Wed 6/10

1:20 pm-9:35 am

1 stop22h 45m

$487

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 6/12

10:15 am-12:35 am

1 stop11h 50m

St John's

Mon 6/15

3:00 pm-9:35 am

1 stop21h 05m

$497

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Tue 6/23

10:25 am-12:35 pm

1 stop23h 40m

St John's

Sun 6/28

6:00 am-9:40 am

2 stops30h 10m

$540

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

$587

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 8/26

3:20 pm-12:55 am

2 stops7h 05m

St John's

Sun 8/30

6:05 am-2:35 pm

2 stops11h 00m

$587

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 7/8

3:20 pm-12:55 am

2 stops7h 05m

St John's

Thu 7/23

6:05 am-2:35 pm

2 stops11h 00m

$598

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Tue 6/23

10:25 am-12:56 am

2 stops12h 01m

St John's

Sun 6/28

6:05 am-2:35 pm

2 stops11h 00m

$598

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 6/17

10:15 am-12:56 am

2 stops12h 11m

St John's

Fri 6/19

6:00 am-2:35 pm

2 stops11h 05m

$604

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 6/13

10:15 am-12:56 am

2 stops12h 11m

St John's

Mon 6/15

6:05 am-2:35 pm

2 stops11h 00m

$606

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 6/12

10:15 am-12:56 am

2 stops12h 11m

St John's

Mon 6/15

4:00 pm-9:35 am

3 stops20h 05m

$628

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 35 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 May 5, 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
11,000 reviews

Food

6.3

Entertainment

6.8

Crew

7.8

Boarding

7.3

Comfort

7.1

Overall

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
11,000 reviews
Air Canada
7.1
Good
11,000 reviews

Food

6.3

Entertainment

6.8

Crew

7.8

Boarding

7.3

Comfort

7.1

Overall

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?

    Porter Airlines, Air Canada, and United Airlines can get you from Chicago to Newfoundland and Labrador in just under 6h 42m. Your travel time can differ by up to 1h 33m. The distance between Chicago and Newfoundland and Labrador is about 1544 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$252Average$624FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$524Average$669FlexibilityNo cancel feeOn-time67%

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