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

Air Canada, United Airlines, and WestJet are the most popular carriers 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 April 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.

$204 Cheap Flights from Chicago to Newfoundland and Labrador in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Newfoundland and Labrador

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:35 pm - 1:50 pm

ORD

YYT

14h 45m

1 stop

4:00 pm - 9:00 am

YYT

ORD

19h 30m

3 stops

$443Multiple Airlines

Thu, May 28 - Wed, Jun 3

10:30 am - 12:35 pm

MDW

YYT

23h 35m

1 stop

7:00 pm - 9:40 am

YYT

MDW

17h 10m

1 stop

$449Multiple Airlines

Thu, May 28 - Wed, Jun 3

2:00 pm - 12:45 am

ORD

YYT

8h 15m

2 stops

5:35 am - 1:10 pm

YYT

ORD

10h 05m

2 stops

$450Air Canada

Mon, Jul 6 - Thu, Jul 9

10:25 am - 12:55 am

MDW

YYT

12h 00m

2 stops

6:05 am - 2:35 pm

YYT

MDW

11h 00m

2 stops

$452Porter Airlines

Sun, Jul 26 - Wed, Jul 29

3:45 pm - 1:46 am

ORD

YYT

7h 31m

1 stop

5:35 am - 10:16 am

YYT

ORD

7h 11m

1 stop

$455Air Canada

Mon, Jul 6 - Thu, Jul 9

8:45 am - 11:28 pm

ORD

YYT

12h 13m

2 stops

8:30 am - 1:22 pm

YYT

ORD

7h 22m

1 stop

$484Air Canada

Sun, Jul 26 - Wed, Jul 29

3:45 pm - 1:46 am

ORD

YYT

7h 31m

1 stop

8:00 pm - 9:00 am

YYT

ORD

15h 30m

1 stop

$485Air Canada

Mon, Jul 13 - Sat, Jul 18

8:45 am - 11:28 pm

ORD

YYT

12h 13m

2 stops

5:35 am - 1:22 pm

YYT

ORD

10h 17m

2 stops

$487Air Canada

Sun, Jul 26 - Wed, Jul 29

10:30 am - 12:55 am

MDW

YYT

11h 55m

2 stops

4:00 pm - 9:40 am

YYT

MDW

20h 10m

3 stops

$503Porter Airlines

Thu, May 28 - Wed, Jun 3

10:00 am - 12:57 am

ORD

YDF

12h 27m

2 stops

5:25 am - 11:21 am

YDF

ORD

8h 26m

1 stop

$696United Airlines

Sun, Sep 6 - Fri, Sep 18

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WestJet flights from Chicago to Newfoundland and Labrador

Our best WestJet deals on Chicago to Newfoundland and Labrador flight tickets

WestJet

Sep 15

MDW10:35 amChicago Midway

9h 50m

2 stops

YYT10:55 pmSt John's

Sep 22

YYT3:00 pmSt John's

24h 41m

2 stops

MDW1:11 pmChicago Midway

$846

WestJet

Apr 29

MDW9:27 amChicago Midway

10h 58m

2 stops

YYT10:55 pmSt John's

May 2

YYT3:00 pmSt John's

20h 17m

2 stops

MDW8:47 amChicago Midway

$1,342

Air Canada flights from Chicago to Newfoundland and Labrador

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

Air Canada

Jul 6

ORD2:00 pmChicago O'Hare Intl

8h 15m

2 stops

YYT12:45 amSt John's

Jul 9

YYT5:35 amSt John's

10h 05m

2 stops

ORD1:10 pmChicago O'Hare Intl

$450

Air Canada

Jul 6

ORD3:45 pmChicago O'Hare Intl

7h 31m

1 stop

YYT1:46 amSt John's

Jul 9

YYT5:35 amSt John's

7h 11m

1 stop

ORD10:16 amChicago O'Hare Intl

$455

Air Canada

Jul 26

ORD8:45 amChicago O'Hare Intl

12h 13m

2 stops

YYT11:28 pmSt John's

Jul 29

YYT8:30 amSt John's

7h 22m

1 stop

ORD1:22 pmChicago O'Hare Intl

$484

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

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 5/28

8:35 pm-1:50 pm

1 stop14h 45m

St John's

Wed 6/3

4:00 pm-9:00 am

3 stops19h 30m

$443

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 5/28

10:30 am-12:35 pm

1 stop23h 35m

St John's

Wed 6/3

7:00 pm-9:40 am

1 stop17h 10m

$449

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Mon 7/6

2:00 pm-12:45 am

2 stops8h 15m

St John's

Thu 7/9

5:35 am-1:10 pm

2 stops10h 05m

$450

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sun 7/26

10:25 am-12:55 am

2 stops12h 00m

St John's

Wed 7/29

6:05 am-2:35 pm

2 stops11h 00m

$452

Quickest round-trip

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Mon 7/6

3:45 pm-1:46 am

1 stop7h 31m

St John's

Thu 7/9

5:35 am-10:16 am

1 stop7h 11m

$455

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sun 7/26

8:45 am-11:28 pm

2 stops12h 13m

St John's

Wed 7/29

8:30 am-1:22 pm

1 stop7h 22m

$484

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Mon 7/13

3:45 pm-1:46 am

1 stop7h 31m

St John's

Sat 7/18

8:00 pm-9:00 am

1 stop15h 30m

$485

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sun 7/26

8:45 am-11:28 pm

2 stops12h 13m

St John's

Wed 7/29

5:35 am-1:22 pm

2 stops10h 17m

$487

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 5/28

10:30 am-12:55 am

2 stops11h 55m

St John's

Wed 6/3

4:00 pm-9:40 am

3 stops20h 10m

$503

ChicagoDeer Lake

ORD - YDF

ORDYDF

Chicago O'Hare Intl

Sun 9/6

10:00 am-12:57 am

2 stops12h 27m

Deer Lake

Fri 9/18

5:25 am-11:21 am

1 stop8h 26m

$696

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 54% 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

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 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 April 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
Air Canada	PriceFrom $524	Free Cancellation	Rating 7.1 10,974 reviews		Search Air Canada flights
United Airlines	PriceFrom $547	Free Cancellation	Rating 7.4 9,665 reviews		Search United Airlines 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.