Cheap flights from Chicago to Newfoundland and Labrador from C$ 279

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 5/9. 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

Find the cheapest flights from Chicago to Newfoundland and Labrador

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:35 p.m. - 1:50 p.m.
ORD
-
YYT
14h 45m
1 stop
Multiple Airlines Logo
4:00 p.m. - 9:00 a.m.
YYT
-
ORD
19h 30m
3 stops
C$ 605Multiple Airlines
Thu, 28 May - Wed, 3 Jun
Multiple Airlines Logo
10:30 a.m. - 12:35 p.m.
MDW
-
YYT
23h 35m
1 stop
Multiple Airlines Logo
7:00 p.m. - 9:40 a.m.
YYT
-
MDW
17h 10m
1 stop
C$ 614Multiple Airlines
Thu, 28 May - Wed, 3 Jun
Air Canada Logo
11:05 a.m. - 11:28 p.m.
ORD
-
YYT
9h 53m
2 stops
Air Canada Logo
5:35 a.m. - 10:16 a.m.
YYT
-
ORD
7h 11m
1 stop
C$ 615Air Canada
Sat, 18 Jul - Fri, 24 Jul
Porter Airlines Logo
10:25 a.m. - 12:55 a.m.
MDW
-
YYT
12h 00m
2 stops
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
C$ 618Porter Airlines
Sun, 26 Jul - Wed, 29 Jul
Air Canada Logo
3:45 p.m. - 1:46 a.m.
ORD
-
YYT
7h 31m
1 stop
Air Canada Logo
5:35 a.m. - 10:16 a.m.
YYT
-
ORD
7h 11m
1 stop
C$ 622Air Canada
Mon, 6 Jul - Thu, 9 Jul
Multiple Airlines Logo
9:55 a.m. - 12:41 a.m.
ORD
-
YYT
12h 16m
2 stops
Multiple Airlines Logo
4:00 p.m. - 9:00 a.m.
YYT
-
ORD
19h 30m
3 stops
C$ 678Multiple Airlines
Thu, 28 May - Wed, 3 Jun
Porter Airlines Logo
10:30 a.m. - 12:55 a.m.
MDW
-
YYT
11h 55m
2 stops
Porter Airlines Logo
4:00 p.m. - 9:40 a.m.
YYT
-
MDW
20h 10m
3 stops
C$ 687Porter Airlines
Thu, 28 May - Wed, 3 Jun
Air Canada Logo
8:45 a.m. - 11:28 p.m.
ORD
-
YYT
12h 13m
2 stops
Air Canada Logo
8:00 p.m. - 9:00 a.m.
YYT
-
ORD
15h 30m
1 stop
C$ 696Air Canada
Sun, 26 Jul - Wed, 29 Jul
Multiple Airlines Logo
10:30 a.m. - 12:35 p.m.
MDW
-
YYT
23h 35m
1 stop
Multiple Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
C$ 700Multiple Airlines
Sun, 24 May - Sun, 31 May
Porter Airlines Logo
10:25 a.m. - 12:55 a.m.
MDW
-
YYT
12h 00m
2 stops
Porter Airlines Logo
7:00 p.m. - 9:40 a.m.
YYT
-
MDW
17h 10m
1 stop
C$ 738Porter Airlines
Sat, 18 Jul - Fri, 24 Jul

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.

WestJet flights from Chicago to Newfoundland and Labrador

Our best WestJet deals on Chicago to Newfoundland and Labrador flight tickets
WestJet
15 Sep
MDW10:35 a.m.Chicago Midway
9h 50m
2 stops
YYT10:55 p.m.St John's
22 Sep
YYT3:00 p.m.St John's
24h 41m
2 stops
MDW1:11 p.m.Chicago Midway
C$ 1,156
WestJet
29 Apr
MDW9:27 a.m.Chicago Midway
10h 58m
2 stops
YYT10:55 p.m.St John's
2 May
YYT3:00 p.m.St John's
20h 17m
2 stops
MDW8:47 a.m.Chicago Midway
C$ 1,834
WestJet
11 Sep
MDW9:30 a.m.Chicago Midway
18h 45m
2 stops
YYT6:45 a.m.St John's
15 Sep
YYT3:00 p.m.St John's
24h 41m
2 stops
MDW1:11 p.m.Chicago Midway
C$ 1,921

Air Canada flights from Chicago to Newfoundland and Labrador

Our best Air Canada deals on Chicago to Newfoundland and Labrador flight tickets
Air Canada
6 Jul
ORD2:00 p.m.Chicago O'Hare Intl
8h 15m
2 stops
YYT12:45 a.m.St John's
9 Jul
YYT5:35 a.m.St John's
10h 05m
2 stops
ORD1:10 p.m.Chicago O'Hare Intl
C$ 615
Air Canada
6 Jul
ORD3:45 p.m.Chicago O'Hare Intl
7h 31m
1 stop
YYT1:46 a.m.St John's
9 Jul
YYT5:35 a.m.St John's
7h 11m
1 stop
ORD10:16 a.m.Chicago O'Hare Intl
C$ 622
Air Canada
26 Jul
ORD8:45 a.m.Chicago O'Hare Intl
12h 13m
2 stops
YYT11:28 p.m.St John's
29 Jul
YYT8:30 a.m.St John's
7h 22m
1 stop
ORD1:22 p.m.Chicago O'Hare Intl
C$ 661

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 27 April 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

Thu 28/5

8:35 p.m.-1:50 p.m.

1 stop14h 45m

St John's

Wed 3/6

4:00 p.m.-9:00 a.m.

3 stops19h 30m

C$ 605

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 28/5

10:30 a.m.-12:35 p.m.

1 stop23h 35m

St John's

Wed 3/6

7:00 p.m.-9:40 a.m.

1 stop17h 10m

C$ 614

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 18/7

11:05 a.m.-11:28 p.m.

2 stops9h 53m

St John's

Fri 24/7

5:35 a.m.-10:16 a.m.

1 stop7h 11m

C$ 615

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sun 26/7

10:25 a.m.-12:55 a.m.

2 stops12h 00m

St John's

Wed 29/7

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

2 stops11h 00m

C$ 618
Quickest round-trip

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Mon 6/7

3:45 p.m.-1:46 a.m.

1 stop7h 31m

St John's

Thu 9/7

5:35 a.m.-10:16 a.m.

1 stop7h 11m

C$ 622

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 28/5

9:55 a.m.-12:41 a.m.

2 stops12h 16m

St John's

Wed 3/6

4:00 p.m.-9:00 a.m.

3 stops19h 30m

C$ 678

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 28/5

10:30 a.m.-12:55 a.m.

2 stops11h 55m

St John's

Wed 3/6

4:00 p.m.-9:40 a.m.

3 stops20h 10m

C$ 687

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sun 26/7

8:45 a.m.-11:28 p.m.

2 stops12h 13m

St John's

Wed 29/7

8:00 p.m.-9:00 a.m.

1 stop15h 30m

C$ 696

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sun 24/5

10:30 a.m.-12:35 p.m.

1 stop23h 35m

St John's

Sun 31/5

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

2 stops11h 00m

C$ 700

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 18/7

10:25 a.m.-12:55 a.m.

2 stops12h 00m

St John's

Fri 24/7

7:00 p.m.-9:40 a.m.

1 stop17h 10m

C$ 738

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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?

WestJet is the most popular carrier 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

7h 05m

Direct flights

None
The fastest flight from Chicago to Newfoundland and Labrador takes 7h 05m
There are no direct flights from Chicago to Newfoundland and Labrador. There are no popular flight routes from Chicago to Newfoundland and Labrador.

Frequently asked questions about flying 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
Wed 27/5
Wed 3/6

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