Cheap flights from Chicago to Newfoundland and Labrador from C$ 358

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 29/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Newfoundland and Labrador

Cheap round-trip flights

 Logo
5:28 p.m. - 12:38 a.m.MDW-YYT
28h 40m2 stops
 Logo
3:00 p.m. - 8:39 a.m.YYT-MDW
20h 09m1 stop
C$ 593
Find Deal
Fri, 10 Oct - Fri, 24 Oct
 Logo
6:30 a.m. - 12:38 a.m.ORD-YYT
15h 38m2 stops
 Logo
6:00 a.m. - 5:27 p.m.YYT-ORD
13h 57m2 stops
C$ 611
Find Deal
Wed, 1 Oct - Wed, 8 Oct
 Logo
5:20 p.m. - 10:56 p.m.MDW-YYT
27h 06m1 stop
 Logo
3:00 p.m. - 8:39 a.m.YYT-MDW
20h 09m1 stop
C$ 654
Find Deal
Fri, 10 Oct - Fri, 24 Oct
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
Porter Airlines Logo
6:00 a.m. - 4:24 p.m.YYT-MDW
12h 54m1 stop
C$ 692Porter Airlines
Find Deal
Fri, 12 Sep - Tue, 16 Sep
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
Porter Airlines Logo
2:55 p.m. - 8:39 a.m.YYT-MDW
20h 14m3 stops
C$ 752Porter Airlines
Find Deal
Fri, 10 Oct - Fri, 24 Oct
Air Canada Logo
3:55 p.m. - 1:33 a.m.ORD-YYT
7h 08m1 stop
Air Canada Logo
5:00 a.m. - 12:05 p.m.YYT-ORD
9h 35m1 stop
C$ 772Air Canada
Find Deal
Tue, 28 Oct - Tue, 4 Nov
Air Canada Logo
3:35 p.m. - 12:39 a.m.ORD-YYT
6h 34m1 stop
Air Canada Logo
2:00 p.m. - 8:11 p.m.YYT-ORD
8h 41m1 stop
C$ 790Air Canada
Find Deal
Sat, 20 Sep - Sat, 27 Sep
United Airlines Logo
8:40 a.m. - 5:09 p.m.ORD-YYT
5h 59m1 stop
United Airlines Logo
5:00 a.m. - 6:50 p.m.YYT-ORD
16h 20m2 stops
C$ 853United Airlines
Find Deal
Tue, 16 Sep - Tue, 23 Sep
United Airlines Logo
8:45 a.m. - 12:39 a.m.ORD-YYT
13h 24m2 stops
United Airlines Logo
5:00 a.m. - 6:50 p.m.YYT-ORD
16h 20m2 stops
C$ 858United Airlines
Find Deal
Tue, 16 Sep - Tue, 23 Sep
WestJet Logo
12:43 p.m. - 6:20 a.m.MDW-YYT
15h 07m2 stops
WestJet Logo
3:00 p.m. - 9:36 p.m.YYT-MDW
33h 06m2 stops
C$ 1,592WestJet
Find Deal
Fri, 12 Sep - Tue, 16 Sep

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 Oct
ORD3:55 p.m.Chicago O'Hare Intl
7h 08m
1 stop
YYT1:33 a.m.St John's
4 Nov
YYT5:00 a.m.St John's
9h 35m
1 stop
ORD12:05 p.m.Chicago O'Hare Intl
Air Canada
20 Sep
ORD3:35 p.m.Chicago O'Hare Intl
6h 34m
1 stop
YYT12:39 a.m.St John's
27 Sep
YYT2:00 p.m.St John's
8h 41m
1 stop
ORD8:11 p.m.Chicago O'Hare Intl
Air Canada
18 Sep
ORD12:00 p.m.Chicago O'Hare Intl
7h 11m
1 stop
YYT9:41 p.m.St John's
21 Sep
YYT5:50 a.m.St John's
6h 31m
1 stop
ORD9:51 a.m.Chicago O'Hare Intl

Porter Airlines flights from Chicago to Newfoundland and Labrador

Our best Porter Airlines deals on Chicago to Newfoundland and Labrador flight tickets
Porter Airlines
12 Sep
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
16 Sep
YYT6:00 a.m.St John's
12h 54m
1 stop
MDW4:24 p.m.Chicago Midway
Porter Airlines
10 Oct
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
24 Oct
YYT2:55 p.m.St John's
20h 14m
3 stops
MDW8:39 a.m.Chicago Midway
Porter Airlines
18 Sep
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
21 Sep
YYT2:55 p.m.St John's
20h 14m
2 stops
MDW8:39 a.m.Chicago Midway

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 18 August 2025.
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

Fri 10/10

5:28 p.m.-12:38 a.m.

2 stops28h 40m

St John's

Fri 24/10

3:00 p.m.-8:39 a.m.

1 stop20h 09m

C$ 593

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 1/10

6:30 a.m.-12:38 a.m.

2 stops15h 38m

St John's

Wed 8/10

6:00 a.m.-5:27 p.m.

2 stops13h 57m

C$ 611

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 10/10

5:20 p.m.-10:56 p.m.

1 stop27h 06m

St John's

Fri 24/10

3:00 p.m.-8:39 a.m.

1 stop20h 09m

C$ 654

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 12/9

9:35 a.m.-12:38 a.m.

2 stops12h 33m

St John's

Tue 16/9

6:00 a.m.-4:24 p.m.

1 stop12h 54m

C$ 692

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 10/10

9:35 a.m.-12:38 a.m.

2 stops12h 33m

St John's

Fri 24/10

2:55 p.m.-8:39 a.m.

3 stops20h 14m

C$ 752

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 28/10

3:55 p.m.-1:33 a.m.

1 stop7h 08m

St John's

Tue 4/11

5:00 a.m.-12:05 p.m.

1 stop9h 35m

C$ 772

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 20/9

3:35 p.m.-12:39 a.m.

1 stop6h 34m

St John's

Sat 27/9

2:00 p.m.-8:11 p.m.

1 stop8h 41m

C$ 790

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 16/9

8:40 a.m.-5:09 p.m.

1 stop5h 59m

St John's

Tue 23/9

5:00 a.m.-6:50 p.m.

2 stops16h 20m

C$ 852

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 16/9

8:45 a.m.-12:39 a.m.

2 stops13h 24m

St John's

Tue 23/9

5:00 a.m.-6:50 p.m.

2 stops16h 20m

C$ 858

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 12/9

12:43 p.m.-6:20 a.m.

2 stops15h 07m

St John's

Tue 16/9

3:00 p.m.-9:36 p.m.

2 stops33h 06m

C$ 1,592

Flights are sorted by cheapest round-trip flights first.

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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?

Air Canada and Delta 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

Best price found

C$ 358

Fastest flight time

5h 59m

Direct flights

None

Airports in Newfoundland and Labrador

1 airport
The best one-way flight to Newfoundland and Labrador from Chicago in the past 72 hours is C$ 358. The best round-trip flight deal from Chicago to Newfoundland and Labrador found on momondo in the last 72 hours is C$ 593.
The fastest flight from Chicago to Newfoundland and Labrador takes 5h 59m
There are no direct flights from Chicago to Newfoundland and Labrador. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - St John's Airport and Chicago Midway Airport - St John's Airport.
There is 1 airport near Newfoundland and Labrador: St John's (YYT)
  • 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.

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Sat 23/8
Sat 30/8

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