Cheap flights from Chicago to Newfoundland and Labrador from C$ 271

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Newfoundland and Labrador departing on 20/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Chicago to Newfoundland and Labrador

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
12:45 p.m. - 11:20 p.m.
MDW
-
YYT
8h 05m2 stops
Porter Airlines Logo
6:15 a.m. - 11:50 a.m.
YYT
-
MDW
8h 05m2 stops
C$ 576Porter Airlines
Sat, 21 Feb - Sat, 28 Feb
Air Canada Logo
3:55 p.m. - 1:58 a.m.
ORD
-
YYT
7h 33m1 stop
Air Canada Logo
5:25 a.m. - 10:30 a.m.
YYT
-
ORD
7h 35m1 stop
C$ 642Air Canada
Sat, 28 Mar - Sun, 29 Mar
Air Canada Logo
3:55 p.m. - 1:58 a.m.
ORD
-
YYT
7h 33m1 stop
Air Canada Logo
5:25 a.m. - 3:10 p.m.
YYT
-
ORD
12h 15m2 stops
C$ 653Air Canada
Sat, 28 Mar - Sun, 29 Mar
Porter Airlines Logo
11:00 a.m. - 1:01 a.m.
MDW
-
YYT
11h 31m2 stops
Porter Airlines Logo
6:00 a.m. - 3:20 p.m.
YYT
-
MDW
11h 50m2 stops
C$ 659Porter Airlines
Sun, 29 Mar - Wed, 1 Apr
Porter Airlines Logo
11:00 a.m. - 11:05 p.m.
MDW
-
YYT
9h 35m2 stops
Porter Airlines Logo
6:00 a.m. - 3:20 p.m.
YYT
-
MDW
11h 50m2 stops
C$ 679Porter Airlines
Thu, 9 Apr - Thu, 16 Apr
Air Canada Logo
7:15 a.m. - 8:15 p.m.
ORD
-
YYT
10h 30m2 stops
Air Canada Logo
5:05 a.m. - 11:06 a.m.
YYT
-
ORD
8h 31m1 stop
C$ 683Air Canada
Sat, 7 Feb - Wed, 11 Feb
Air Canada Logo
7:15 a.m. - 8:15 p.m.
ORD
-
YYT
10h 30m2 stops
Air Canada Logo
7:30 a.m. - 5:45 p.m.
YYT
-
ORD
12h 45m2 stops
C$ 690Air Canada
Wed, 25 Mar - Mon, 30 Mar
Air Canada Logo
7:15 a.m. - 8:15 p.m.
ORD
-
YYT
10h 30m2 stops
Air Canada Logo
5:25 a.m. - 1:00 p.m.
YYT
-
ORD
10h 05m2 stops
C$ 694Air Canada
Wed, 25 Mar - Sun, 29 Mar
Air Canada Logo
7:55 a.m. - 5:03 p.m.
ORD
-
YYT
6h 38m1 stop
Air Canada Logo
10:15 a.m. - 5:45 p.m.
YYT
-
ORD
10h 00m2 stops
C$ 697Air Canada
Sun, 29 Mar - Tue, 31 Mar
Multiple Airlines Logo
2:41 p.m. - 2:10 p.m.
MDW
-
YYT
20h 59m2 stops
Multiple Airlines Logo
3:35 p.m. - 3:33 p.m.
YYT
-
MDW
26h 28m1 stop
C$ 840Multiple Airlines
Thu, 26 Mar - Mon, 30 Mar

Porter Airlines flights from Chicago to Newfoundland and Labrador

Our best Porter Airlines deals on Chicago to Newfoundland and Labrador flight tickets
Porter Airlines
21 Feb
MDW12:45 p.m.Chicago Midway
8h 05m
2 stops
YYT11:20 p.m.St John's
28 Feb
YYT6:15 a.m.St John's
8h 05m
2 stops
MDW11:50 a.m.Chicago Midway
Porter Airlines
29 Mar
MDW11:00 a.m.Chicago Midway
11h 31m
2 stops
YYT1:01 a.m.St John's
1 Apr
YYT6:00 a.m.St John's
11h 50m
2 stops
MDW3:20 p.m.Chicago Midway
Porter Airlines
9 Apr
MDW11:00 a.m.Chicago Midway
9h 35m
2 stops
YYT11:05 p.m.St John's
16 Apr
YYT6:00 a.m.St John's
11h 50m
2 stops
MDW3:20 p.m.Chicago Midway

Air Canada flights from Chicago to Newfoundland and Labrador

Our best Air Canada deals on Chicago to Newfoundland and Labrador flight tickets
Air Canada
28 Mar
ORD3:55 p.m.Chicago O'Hare Intl
7h 33m
1 stop
YYT1:58 a.m.St John's
29 Mar
YYT5:25 a.m.St John's
7h 35m
1 stop
ORD10:30 a.m.Chicago O'Hare Intl
Air Canada
28 Mar
ORD3:55 p.m.Chicago O'Hare Intl
7h 33m
1 stop
YYT1:58 a.m.St John's
29 Mar
YYT5:25 a.m.St John's
12h 15m
2 stops
ORD3:10 p.m.Chicago O'Hare Intl
Air Canada
7 Feb
ORD7:15 a.m.Chicago O'Hare Intl
10h 30m
2 stops
YYT8:15 p.m.St John's
11 Feb
YYT5:05 a.m.St John's
8h 31m
1 stop
ORD11:06 a.m.Chicago O'Hare Intl

momondo 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, momondo users made 96,600 searches. Data last updated 7 January 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

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 21/2

12:45 p.m.-11:20 p.m.

2 stops8h 05m

St John's

Sat 28/2

6:15 a.m.-11:50 a.m.

2 stops8h 05m

C$ 576

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 28/3

3:55 p.m.-1:58 a.m.

1 stop7h 33m

St John's

Sun 29/3

5:25 a.m.-10:30 a.m.

1 stop7h 35m

C$ 642

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 28/3

3:55 p.m.-1:58 a.m.

1 stop7h 33m

St John's

Sun 29/3

5:25 a.m.-3:10 p.m.

2 stops12h 15m

C$ 653

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sun 29/3

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

2 stops11h 31m

St John's

Wed 1/4

6:00 a.m.-3:20 p.m.

2 stops11h 50m

C$ 659

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 9/4

11:00 a.m.-11:05 p.m.

2 stops9h 35m

St John's

Thu 16/4

6:00 a.m.-3:20 p.m.

2 stops11h 50m

C$ 679

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 7/2

7:15 a.m.-8:15 p.m.

2 stops10h 30m

St John's

Wed 11/2

5:05 a.m.-11:06 a.m.

1 stop8h 31m

C$ 683

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 25/3

7:15 a.m.-8:15 p.m.

2 stops10h 30m

St John's

Mon 30/3

7:30 a.m.-5:45 p.m.

2 stops12h 45m

C$ 690

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 25/3

7:15 a.m.-8:15 p.m.

2 stops10h 30m

St John's

Sun 29/3

5:25 a.m.-1:00 p.m.

2 stops10h 05m

C$ 694

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sun 29/3

7:55 a.m.-5:03 p.m.

1 stop6h 38m

St John's

Tue 31/3

10:15 a.m.-5:45 p.m.

2 stops10h 00m

C$ 697

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 26/3

2:41 p.m.-2:10 p.m.

2 stops20h 59m

St John's

Mon 30/3

3:35 p.m.-3:33 p.m.

1 stop26h 28m

C$ 840

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

See travel insights to Newfoundland and Labrador from

How to get the cheapest flight ticket from Chicago to Newfoundland and Labrador

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago to Newfoundland and Labrador?

Porter Airlines, Air Canada, and United Airlines are the most popular carriers operating from Chicago to Newfoundland and Labrador

Cheap Chicago to Newfoundland and Labrador flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Newfoundland and Labrador

Fastest flight time

6h 25m

Direct flights

None
The fastest flight from Chicago to Newfoundland and Labrador takes 6h 25m
There are no direct flights from Chicago to Newfoundland and Labrador. There are no popular flight routes from Chicago to Newfoundland and Labrador.
  • When did momondo last update prices for flights from Chicago to Newfoundland and Labrador?

    Prices for flights from Chicago to Newfoundland and Labrador refresh daily.

  • How old do you have to be to fly from Chicago to Newfoundland and Labrador?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Newfoundland and Labrador.

  • What documentation or ID do you need to fly to Newfoundland and Labrador?

    The necessary travel and health documents for your Newfoundland and Labrador trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Newfoundland and Labrador?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Newfoundland and Labrador from Chicago.

Can I find flights from Chicago to Newfoundland and Labrador with flexible booking policies on momondo?

Flights from Chicago to Newfoundland and Labrador with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Newfoundland and Labrador?

Once you have performed a search for Chicago to Newfoundland and Labrador flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Newfoundland and Labrador right now. Can momondo alert me if prices change?

Price alerts on flights to Newfoundland and Labrador from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Newfoundland and Labrador trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 6/2
Fri 13/2

Find better results for your trip to Newfoundland and Labrador

Popular Cities in Newfoundland and Labrador

Popular flights according to clicks in the last 7 days on momondo