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Newfoundland and Labrador

$439+ Cheap flights from Chicago (CHI) to Newfoundland and Labrador

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
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 December 17, 2025.

This oojo deal was found by Cheapflights users on 12/16. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:00 amMDW - YYT
2 stops11h 33mPorter Airlines
Tue 12/306:20 amYYT - MDW
2 stops11h 30mPorter Airlines
Deal found 12/16$1,026
This Air Canada deal was found by Cheapflights users on 12/16. 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.
Tue 12/233:35 pmORD - YYT
1 stop6h 51mAir Canada
Tue 12/305:05 amYYT - ORD
1 stop8h 43mAir Canada
Deal found 12/16$1,048
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/239:15 pmORD - YYT
2 stops17h 36mUnited Airlines
Tue 12/305:05 amYYT - ORD
1 stop8h 43mUnited Airlines
Deal found 12/16$1,052
This Gotogate deal was found by Cheapflights users on 12/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:00 amMDW - YYT
2 stops11h 33mPorter Airlines
Sat 12/206:00 amYYT - MDW
2 stops11h 50mPorter Airlines
Deal found 12/14$1,299
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/199:20 pmORD - YYT
1 stop12h 45mUnited Airlines
Sun 12/211:30 pmYYT - ORD
1 stop8h 45mUnited Airlines
Deal found 12/15$1,371
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1711:15 amORD - YYT
1 stop9h 48mUnited Airlines
Wed 12/245:05 amYYT - ORD
1 stop8h 43mUnited Airlines
Deal found 12/16$1,384
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1911:00 amMDW - YYT
2 stops9h 45mPorter Airlines
Sun 12/214:15 pmYYT - MDW
2 stops20h 20mPorter Airlines
Deal found 12/15$1,500
This Air Canada deal was found by Cheapflights users on 12/15. 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.
Fri 12/192:00 pmORD - YYT
1 stop7h 03mAir Canada
Sun 12/215:05 amYYT - ORD
1 stop8h 43mAir Canada
Deal found 12/15$1,544
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Wed 12/179:14 pmORD - YYT
3 stops23h 31mMultiple Airlines
Wed 12/246:00 amYYT - ORD
2 stops15h 32mMultiple Airlines
Deal found 12/16$1,633
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Wed 12/1711:00 amMDW - YYT
2 stops33h 45mPorter Airlines
Wed 12/246:00 amYYT - MDW
3 stops35h 50mPorter Airlines
Deal found 12/16$2,346

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 December 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$439
(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

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 December 17, 2025.
Use the filters below to find and compare flights from Chicago to Newfoundland and Labrador that are best for you.

Fly from

Chicago

Fly to

Newfoundland and Labrador

Route

Depart

Return

Price

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 1/29

12:44 pm-1:01 am

2 stops33h 47m

St John's

Thu 2/5

9:45 am-1:35 pm

1 stop30h 20m

$439

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 1/29

7:15 am-8:15 pm

2 stops10h 30m

St John's

Mon 2/2

10:15 am-7:45 pm

2 stops12h 00m

$562

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 2/3

2:00 pm-11:13 pm

1 stop6h 43m

St John's

Tue 3/31

5:00 am-1:00 pm

1 stop10h 30m

$575

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 5/21

5:30 pm-6:20 am

1 stop34h 20m

St John's

Sun 5/31

7:10 am-4:43 pm

1 stop12h 03m

$586

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 5/8

5:30 pm-10:55 pm

3 stops26h 55m

St John's

Fri 5/15

1:10 pm-7:59 am

2 stops21h 19m

$595

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 6/10

8:45 am-5:11 pm

1 stop5h 56m

St John's

Wed 6/17

5:20 am-9:53 am

1 stop7h 03m

$609

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 1/14

7:15 am-5:21 pm

1 stop7h 36m

St John's

Wed 1/21

5:05 am-11:06 am

1 stop8h 31m

$609

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 5/7

3:40 pm-12:41 am

1 stop6h 31m

St John's

Sun 5/17

1:15 pm-8:08 pm

1 stop9h 23m

$609

ChicagoDeer Lake

ORD - YDF

ORDYDF

Chicago O'Hare Intl

Sun 5/24

8:45 am-4:35 pm

1 stop5h 20m

Deer Lake

Thu 5/28

5:15 am-4:59 pm

1 stop14h 14m

$631

ChicagoDeer Lake

ORD - YDF

ORDYDF

Chicago O'Hare Intl

Wed 4/29

12:50 pm-10:46 pm

1 stop7h 26m

Deer Lake

Fri 5/1

5:15 am-1:25 pm

1 stop10h 40m

$641

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 15 results
1
2

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

What is the cheapest time of day to fly from CHI to NL?

Find hourly flight availability from Chicago to Newfoundland and Labrador. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 17, 2025.

It’s typically best to fly out from Chicago to Newfoundland and Labrador in the evening. Doing so could potentially save you 24% on the flight price compared to flying in the morning, which is usually more expensive.

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 December 17, 2025.
Peruse reviews from past customers who have flown with United Airlines and 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.
United Airlines
7.4
Good
9,092 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Air Canada
7.1
Good
10,531 reviews
United Airlines
7.4
Good
9,092 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 10h 30m. Your travel time can differ by up to 24h 56m. 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

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Alternative routes for Chicago to Newfoundland and Labrador

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$252Average$602FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$363Average$603FlexibilityNo cancel feeOn-time67%

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