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Cheap flights from Chicago to Newfoundland and Labrador from C$ 401

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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
4 Jun — 11 Jun1
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 5 May 2026.

Thu 4/610:15 a.m.
MDW
-
YYT
2 stops12h 11m
Multiple Airlines
Wed 10/61:20 p.m.
YYT
-
MDW
1 stop22h 45m
Multiple Airlines
Deal found 1/5C$ 663
Fri 12/610:15 a.m.
MDW
-
YYT
1 stop11h 50m
Multiple Airlines
Mon 15/63:00 p.m.
YYT
-
MDW
1 stop21h 05m
Multiple Airlines
Deal found 3/5C$ 676
Wed 3/610:15 a.m.
MDW
-
YYT
2 stops36h 11m
Multiple Airlines
Wed 24/63:00 p.m.
YYT
-
MDW
1 stop21h 10m
Multiple Airlines
Deal found 5/5C$ 712
Tue 23/610:25 a.m.
MDW
-
YYT
1 stop23h 40m
Multiple Airlines
Sun 28/66:00 a.m.
YYT
-
MDW
2 stops30h 10m
Multiple Airlines
Deal found 2/5C$ 735
Thu 4/67:25 a.m.
ORD
-
YYT
2 stops15h 01m
Multiple Airlines
Wed 10/66:05 a.m.
YYT
-
ORD
2 stops16h 41m
Multiple Airlines
Deal found 1/5C$ 751
Mon 8/610:15 a.m.
MDW
-
YYT
2 stops12h 11m
Porter Airlines
Mon 15/66:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 3/5C$ 752
Thu 4/62:00 p.m.
ORD
-
YYT
1 stop9h 18m
Air Canada
Wed 10/66:10 p.m.
YYT
-
ORD
2 stops17h 20m
Air Canada
Deal found 1/5C$ 771
Sat 17/1011:45 a.m.
ORD
-
YYT
2 stops10h 40m
Porter Airlines
Sat 24/106:05 a.m.
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 2/5C$ 782
Sun 18/103:20 p.m.
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Fri 23/106:05 a.m.
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 5/5C$ 784
Fri 5/610:15 a.m.
MDW
-
YYT
2 stops12h 11m
Porter Airlines
Mon 8/66:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 3/5C$ 792
Mon 6/73:20 p.m.
MDW
-
YYT
2 stops7h 05m
Porter Airlines
Thu 9/76:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 1/5C$ 799
Wed 30/93:20 p.m.
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sat 10/106:05 a.m.
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 1/5C$ 808

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 5 May 2026.

Round-trip from

C$ 663

One-way from

C$ 401
4/6-10/6
  • 4/6-10/6
  • 3 total stops
  • 34h 56m total
  • Chicago to Newfoundland and Labrador
Search Deals
Air Canada
  • Air Canada
  • 5/9
  • 1 total stop
  • 5h 55m 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 5 May 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 4/6

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

2 stops12h 11m

St John's

Wed 10/6

1:20 p.m.-9:35 a.m.

1 stop22h 45m

C$ 663

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 12/6

10:15 a.m.-12:35 a.m.

1 stop11h 50m

St John's

Mon 15/6

3:00 p.m.-9:35 a.m.

1 stop21h 05m

C$ 676

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Tue 23/6

10:25 a.m.-12:35 p.m.

1 stop23h 40m

St John's

Sun 28/6

6:00 a.m.-9:40 a.m.

2 stops30h 10m

C$ 735

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 4/6

2:00 p.m.-1:48 a.m.

1 stop9h 18m

St John's

Wed 10/6

6:10 p.m.-9:00 a.m.

2 stops17h 20m

C$ 771

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$ 799

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Mon 6/7

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

2 stops7h 05m

St John's

Thu 9/7

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

2 stops11h 00m

C$ 799

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Tue 23/6

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

2 stops12h 01m

St John's

Sun 28/6

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

2 stops11h 00m

C$ 814

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 8/7

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

2 stops7h 05m

St John's

Thu 23/7

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

2 stops11h 00m

C$ 814
Quickest round-trip

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 22/9

2:15 p.m.-11:21 p.m.

1 stop6h 36m

St John's

Tue 29/9

5:35 a.m.-10:17 a.m.

1 stop7h 12m

C$ 845

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 30/9

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

2 stops7h 05m

St John's

Sat 10/10

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

2 stops11h 00m

C$ 845

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 30 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 5h 53m. The time it takes to get you to your destination can typically vary by up to 1h 12m. 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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