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

Air Canada is the most popular carrier operating from Chicago to Newfoundland and Labrador

How many operators does momondo search for flights from Chicago to Newfoundland and Labrador?

There are 2 operators available for flights from Chicago to Newfoundland and Labrador as of March 2026.

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.

$255 Cheap Flights from Chicago to Newfoundland and Labrador in 2026

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Find the cheapest flights from Chicago to Newfoundland and Labrador

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:30 am - 1:01 am

MDW

YYT

15h 01m

2 stops

1:20 pm - 9:40 am

YYT

MDW

22h 50m

1 stop

$490Multiple Airlines

Sat, Apr 25 - Mon, May 4

12:55 pm - 4:45 pm

MDW

YYT

25h 20m

1 stop

1:20 pm - 9:40 am

YYT

MDW

22h 50m

1 stop

$493Multiple Airlines

Sat, Apr 25 - Mon, May 4

9:50 am - 11:28 pm

ORD

YYT

11h 08m

2 stops

2:00 pm - 8:08 pm

YYT

ORD

8h 38m

1 stop

$529Air Canada

Sat, Apr 25 - Mon, May 4

9:50 am - 11:28 pm

ORD

YYT

11h 08m

2 stops

5:35 am - 1:25 pm

YYT

ORD

10h 20m

2 stops

$537Air Canada

Sat, Apr 25 - Mon, May 4

9:50 am - 10:58 pm

ORD

YYT

10h 38m

1 stop

1:20 pm - 7:25 pm

YYT

ORD

8h 35m

1 stop

$549Multiple Airlines

Sat, Apr 25 - Mon, May 4

3:20 pm - 12:56 am

MDW

YYT

7h 06m

2 stops

6:05 am - 2:35 pm

YYT

MDW

11h 00m

2 stops

$552Porter Airlines

Thu, May 21 - Thu, May 28

3:20 pm - 12:55 am

ORD

YYT

7h 05m

2 stops

6:05 am - 2:35 pm

YYT

ORD

11h 00m

2 stops

$557Porter Airlines

Fri, Sep 4 - Sun, Sep 13

10:25 am - 12:55 am

MDW

YYT

12h 00m

2 stops

6:05 am - 2:35 pm

YYT

MDW

11h 00m

2 stops

$568Porter Airlines

Wed, Aug 26 - Sun, Aug 30

3:40 pm - 12:45 am

ORD

YYT

6h 35m

1 stop

5:35 am - 10:19 am

YYT

ORD

7h 14m

1 stop

$610Air Canada

Wed, Aug 26 - Sun, Aug 30

3:45 pm - 1:48 am

ORD

YYT

7h 33m

1 stop

5:35 am - 10:16 am

YYT

ORD

7h 11m

1 stop

$615Air Canada

Fri, Jun 12 - Fri, Jun 19

Air Canada flights from Chicago to Newfoundland and Labrador

Our best Air Canada deals on Chicago to Newfoundland and Labrador flight tickets

Air Canada

Apr 25

ORD9:50 amChicago O'Hare Intl

11h 08m

2 stops

YYT11:28 pmSt John's

May 4

YYT2:00 pmSt John's

8h 38m

1 stop

ORD8:08 pmChicago O'Hare Intl

$529

Air Canada

Apr 25

ORD9:50 amChicago O'Hare Intl

11h 08m

2 stops

YYT11:28 pmSt John's

May 4

YYT5:35 amSt John's

10h 20m

2 stops

ORD1:25 pmChicago O'Hare Intl

$537

Air Canada

Aug 26

ORD3:40 pmChicago O'Hare Intl

6h 35m

1 stop

YYT12:45 amSt John's

Aug 30

YYT5:35 amSt John's

7h 14m

1 stop

ORD10:19 amChicago O'Hare Intl

$610

Porter Airlines flights from Chicago to Newfoundland and Labrador

Our best Porter Airlines deals on Chicago to Newfoundland and Labrador flight tickets

Porter Airlines

May 21

MDW3:20 pmChicago Midway

7h 06m

2 stops

YYT12:56 amSt John's

May 28

YYT6:05 amSt John's

11h 00m

2 stops

MDW2:35 pmChicago Midway

$552

Porter Airlines

Sep 4

ORD3:20 pmChicago O'Hare Intl

7h 05m

2 stops

YYT12:55 amSt John's

Sep 13

YYT6:05 amSt John's

11h 00m

2 stops

ORD2:35 pmChicago O'Hare Intl

$557

Porter Airlines

Aug 26

MDW10:25 amChicago Midway

12h 00m

2 stops

YYT12:55 amSt John's

Aug 30

YYT6:05 amSt John's

11h 00m

2 stops

MDW2:35 pmChicago Midway

$568

momondo Fare Finder

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

Sat 4/25

7:30 am-1:01 am

2 stops15h 01m

St John's

Mon 5/4

1:20 pm-9:40 am

1 stop22h 50m

$490

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 4/25

12:55 pm-4:45 pm

1 stop25h 20m

St John's

Mon 5/4

1:20 pm-9:40 am

1 stop22h 50m

$493

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 4/25

9:50 am-11:28 pm

2 stops11h 08m

St John's

Mon 5/4

2:00 pm-8:08 pm

1 stop8h 38m

$529

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 4/25

9:50 am-11:28 pm

2 stops11h 08m

St John's

Mon 5/4

5:35 am-1:25 pm

2 stops10h 20m

$537

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 4/25

9:50 am-10:58 pm

1 stop10h 38m

St John's

Mon 5/4

1:20 pm-7:25 pm

1 stop8h 35m

$549

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 5/21

3:20 pm-12:56 am

2 stops7h 06m

St John's

Thu 5/28

6:05 am-2:35 pm

2 stops11h 00m

$552

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 9/4

3:20 pm-12:55 am

2 stops7h 05m

St John's

Sun 9/13

6:05 am-2:35 pm

2 stops11h 00m

$557

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 8/26

10:25 am-12:55 am

2 stops12h 00m

St John's

Sun 8/30

6:05 am-2:35 pm

2 stops11h 00m

$568

Quickest round-trip

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 8/26

3:40 pm-12:45 am

1 stop6h 35m

St John's

Sun 8/30

5:35 am-10:19 am

1 stop7h 14m

$610

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 6/12

3:45 pm-1:48 am

1 stop7h 33m

St John's

Fri 6/19

5:35 am-10:16 am

1 stop7h 11m

$615

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first

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

Prices

Airlines

Can stopping save me money on Chicago to Newfoundland and Labrador flights?

You could potentially save up to 57% on your flight if you consider stops on a Chicago to Newfoundland and Labrador flight.

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	5h 20m
Direct flights	None

The fastest flight from Chicago to Newfoundland and Labrador takes 5h 20m

There are no direct flights from Chicago to Newfoundland and Labrador. There are no popular flight routes from Chicago to Newfoundland and Labrador.

Search flight deals

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 many operators does momondo search for flights from Chicago to Newfoundland and Labrador?
There are 2 operators available for flights from Chicago to Newfoundland and Labrador as of March 2026.
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.

Best airlines flying from Chicago to Newfoundland and Labrador

Compare and see reviews for airlines that fly from Chicago to Newfoundland and Labrador with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $225	Free Cancellation	Rating 7.4 9,413 reviews		Search United Airlines flights
Air Canada	PriceFrom $524	Free Cancellation	Rating 7.1 10,800 reviews		Search Air Canada flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Newfoundland and Labrador. momondo saves you time and could save you money on your trip.

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

All flight searches from Chicago to Newfoundland and Labrador on momondo can be filtered to show those which offer flexible booking policies.

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

Once all potential Chicago to Newfoundland and Labrador flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Newfoundland and Labrador, momondo offers a useful price alert feature which will track prices for flights to Newfoundland and Labrador from Chicago and alert you when they change.