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 September 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.

$162 Cheap Flights from Chicago to Newfoundland and Labrador in 2026/27

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.

11:45 am - 12:55 amMDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

6:00 am - 2:35 pmYYT St John's-MDW Chicago Midway

11h 05m2 stops Montreal St Hubert Toronto Island

$532Porter Airlines

Tue, Sep 29 - Fri, Oct 2

11:45 am - 12:55 amMDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

6:00 am - 2:35 pmYYT St John's-MDW Chicago Midway

11h 05m2 stops Montreal St Hubert Toronto Island

$549Porter Airlines

Wed, Oct 7 - Wed, Oct 14

12:20 pm - 12:57 amORD Chicago O'Hare Intl-YYT St John's

10h 07m2 stops Toronto Island Ottawa

6:00 am - 5:40 pmYYT St John's-ORD Chicago O'Hare Intl

14h 10m2 stops Ottawa Toronto Island

$551Porter Airlines

Sat, Oct 31 - Sat, Nov 7

3:45 pm - 1:46 amORD Chicago O'Hare Intl-YYT St John's

7h 31m1 stop Toronto Pearson Intl

8:30 am - 2:55 pmYYT St John's-ORD Chicago O'Hare Intl

8h 55m1 stop Toronto Pearson Intl

$563Air Canada

Wed, Oct 14 - Tue, Oct 20

2:15 pm - 11:21 pmORD Chicago O'Hare Intl-YYT St John's

6h 36m1 stop Toronto Pearson Intl

8:30 am - 2:55 pmYYT St John's-ORD Chicago O'Hare Intl

8h 55m1 stop Toronto Pearson Intl

$563Air Canada

Sat, Oct 17 - Fri, Oct 23

6:20 pm - 3:30 pmORD Chicago O'Hare Intl-YYT St John's

18h 40m3 stops Toronto Island Ottawa Halifax Intl

6:00 am - 5:40 pmYYT St John's-ORD Chicago O'Hare Intl

14h 10m2 stops Ottawa Toronto Island

$567Porter Airlines

Sat, Oct 31 - Sat, Nov 7

3:45 pm - 1:46 amORD Chicago O'Hare Intl-YYT St John's

7h 31m1 stop Toronto Pearson Intl

8:30 am - 2:55 pmYYT St John's-ORD Chicago O'Hare Intl

8h 55m1 stop Toronto Pearson Intl

$571Air Canada

Sat, Oct 10 - Fri, Oct 16

5:59 pm - 5:08 pmORD Chicago O'Hare Intl-YYT St John's

20h 39m2 stops New York LaGuardia Montreal Pierre Elliott Trudeau Intl

5:45 am - 5:12 pmYYT St John's-ORD Chicago O'Hare Intl

13h 57m2 stops Montreal Pierre Elliott Trudeau Intl New York LaGuardia

$826United Airlines

Sat, Oct 10 - Fri, Oct 16

3:45 pm - 12:46 amORD Chicago O'Hare Intl-YYT St John's

6h 31m1 stop Montreal Pierre Elliott Trudeau Intl

6:35 am - 1:13 pmYYT St John's-ORD Chicago O'Hare Intl

9h 08m1 stop Toronto Pearson Intl

$960United Airlines

Sat, Mar 13 - Sat, Mar 20

4:40 pm - 1:35 amORD Chicago O'Hare Intl-YYT St John's

6h 25m1 stop Toronto Pearson Intl

5:15 am - 12:27 pmYYT St John's-ORD Chicago O'Hare Intl

9h 42m2 stops Montreal Pierre Elliott Trudeau Intl Boston Logan Intl

$1,182United Airlines

Sat, Mar 13 - Sat, Mar 20

Cheap last minute flights

Enter your travel dates to find the best prices.

11:45 am - 12:55 amMDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

6:00 am - 2:35 pmYYT St John's-MDW Chicago Midway

11h 05m2 stops Montreal St Hubert Toronto Island

$811Porter Airlines

Tue, Sep 22 - Sat, Sep 26

11:45 am - 12:55 amMDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

6:00 am - 2:35 pmYYT St John's-MDW Chicago Midway

11h 05m2 stops Montreal St Hubert Toronto Island

$830Porter Airlines

Tue, Sep 22 - Sat, Sep 26

3:45 pm - 12:58 amORD Chicago O'Hare Intl-YDF Deer Lake

6h 43m1 stop Toronto Pearson Intl

2:25 pm - 7:48 pmYDF Deer Lake-ORD Chicago O'Hare Intl

7h 53m1 stop Toronto Pearson Intl

$840Air Canada

Fri, Sep 25 - Sun, Oct 4

3:20 pm - 12:55 amMDW Chicago Midway-YYT St John's

7h 05m2 stops Toronto Island Ottawa

6:05 am - 2:35 pmYYT St John's-MDW Chicago Midway

11h 00m2 stops Ottawa Toronto Island

$873Porter Airlines

Tue, Sep 22 - Sun, Sep 27

3:45 pm - 1:46 amORD Chicago O'Hare Intl-YYT St John's

7h 31m1 stop Toronto Pearson Intl

5:00 am - 1:23 pmYYT St John's-ORD Chicago O'Hare Intl

10h 53m1 stop Toronto Pearson Intl

$888Air Canada

Tue, Sep 22 - Sun, Sep 27

5:00 am - 4:34 pmORD Chicago O'Hare Intl-YDF Deer Lake

9h 04m2 stops Newark Montreal Pierre Elliott Trudeau Intl

5:00 am - 9:00 amYDF Deer Lake-ORD Chicago O'Hare Intl

6h 30m1 stop Toronto Pearson Intl

$894Air Canada

Fri, Sep 25 - Sun, Oct 4

3:42 pm - 6:05 pmORD Chicago O'Hare Intl-YYT St John's

23h 53m1 stop Toronto Pearson Intl

8:45 am - 4:18 pmYYT St John's-ORD Chicago O'Hare Intl

10h 03m2 stops Halifax Intl Toronto Pearson Intl

$922Porter Airlines

Wed, Sep 23 - Sat, Sep 26

3:40 pm - 12:33 amORD Chicago O'Hare Intl-YYT St John's

6h 23m1 stop Montreal Pierre Elliott Trudeau Intl

7:35 am - 2:52 pmYYT St John's-ORD Chicago O'Hare Intl

9h 47m2 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl

$951Air Canada

Wed, Sep 23 - Sat, Sep 26

8:45 am - 5:08 pmORD Chicago O'Hare Intl-YYT St John's

5h 53m1 stop Montreal Pierre Elliott Trudeau Intl

5:35 am - 10:15 amYYT St John's-ORD Chicago O'Hare Intl

7h 10m1 stop Montreal Pierre Elliott Trudeau Intl

$951Air Canada

Wed, Sep 23 - Sat, Sep 26

8:45 am - 8:03 pmORD Chicago O'Hare Intl-YYT St John's

8h 48m2 stops Montreal Pierre Elliott Trudeau Intl Halifax Intl

7:35 am - 2:52 pmYYT St John's-ORD Chicago O'Hare Intl

9h 47m2 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl

$951Air Canada

Wed, Sep 23 - Sat, Sep 26

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Air Canada flights from Chicago to Newfoundland and Labrador

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

Air Canada

Oct 14

ORD3:45 pmChicago O'Hare Intl

7h 31m

1 stop

YYT1:46 amSt John's

Oct 20

YYT8:30 amSt John's

8h 55m

1 stop

ORD2:55 pmChicago O'Hare Intl

$563

Air Canada

Oct 10

ORD3:45 pmChicago O'Hare Intl

7h 31m

1 stop

YYT1:46 amSt John's

Oct 16

YYT8:30 amSt John's

8h 55m

1 stop

ORD2:55 pmChicago O'Hare Intl

$571

Air Canada

Nov 24

ORD12:50 pmChicago O'Hare Intl

8h 06m

1 stop

YYT11:26 pmSt John's

Nov 28

YYT6:00 amSt John's

9h 43m

1 stop

ORD1:13 pmChicago O'Hare Intl

$573

Porter Airlines flights from Chicago to Newfoundland and Labrador

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

Porter Airlines

Sep 29

MDW11:45 amChicago Midway

10h 40m

2 stops

YYT12:55 amSt John's

Oct 2

YYT6:00 amSt John's

11h 05m

2 stops

MDW2:35 pmChicago Midway

$532

Porter Airlines

Oct 7

MDW11:45 amChicago Midway

10h 40m

2 stops

YYT12:55 amSt John's

Oct 14

YYT6:00 amSt John's

11h 05m

2 stops

MDW2:35 pmChicago Midway

$549

Porter Airlines

Oct 31

ORD12:20 pmChicago O'Hare Intl

10h 07m

2 stops

YYT12:57 amSt John's

Nov 7

YYT6:00 amSt John's

14h 10m

2 stops

ORD5:40 pmChicago O'Hare Intl

$551

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 Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Tue 9/29

11:45 am-12:55 am

2 stops10h 40m

St John's

Fri 10/2

6:00 am-2:35 pm

2 stops11h 05m

$532

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Wed 10/7

11:45 am-12:55 am

2 stops10h 40m

St John's

Wed 10/14

6:00 am-2:35 pm

2 stops11h 05m

$549

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Sat 10/31

12:20 pm-12:57 am

2 stops10h 07m

St John's

Sat 11/7

6:00 am-5:40 pm

2 stops14h 10m

$551

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Wed 10/14

3:45 pm-1:46 am

1 stop7h 31m

St John's

Tue 10/20

8:30 am-2:55 pm

1 stop8h 55m

$563

Quickest round-trip

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Sat 10/17

2:15 pm-11:21 pm

1 stop6h 36m

St John's

Fri 10/23

8:30 am-2:55 pm

1 stop8h 55m

$563

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Sat 10/31

6:20 pm-3:30 pm

3 stops18h 40m

St John's

Sat 11/7

6:00 am-5:40 pm

2 stops14h 10m

$567

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Sat 10/10

3:45 pm-1:46 am

1 stop7h 31m

St John's

Fri 10/16

8:30 am-2:55 pm

1 stop8h 55m

$571

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Sat 10/10

5:59 pm-5:08 pm

2 stops20h 39m

St John's

Fri 10/16

5:45 am-5:12 pm

2 stops13h 57m

$826

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Sat 3/13

3:45 pm-12:46 am

1 stop6h 31m

St John's

Sat 3/20

6:35 am-1:13 pm

1 stop9h 08m

$960

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Sat 3/13

4:40 pm-1:35 am

1 stop6h 25m

St John's

Sat 3/20

5:15 am-12:27 pm

2 stops9h 42m

$1,182

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

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

Porter Airlines and Air Canada 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	$162
Fastest flight time	5h 19m
Direct flights	None

The best one-way flight to Newfoundland and Labrador from Chicago in the past 72 hours is $162. The best round-trip flight deal from Chicago to Newfoundland and Labrador found on momondo in the last 72 hours is $532.

The fastest flight from Chicago to Newfoundland and Labrador takes 5h 19m

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 September 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 $559	Free Cancellation	Rating 7.1 11,654 reviews		Search Air Canada flights
United Airlines	PriceFrom $614	Free Cancellation	Rating 7.4 10,229 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.