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Cheap flights from Chicago to Newfoundland and Labrador from $143

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 10/29. 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

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Multiple Airlines Logo
6:48 am - 1:01 amORD-YYT
15h 43m2 stops
Multiple Airlines Logo
6:00 am - 10:39 amYYT-ORD
31h 09m3 stops
$441Multiple Airlines
Find Deal
Sat, Nov 15 - Sat, Nov 22
Multiple Airlines Logo
5:25 am - 2:28 pmORD-YYT
30h 33m1 stop
Multiple Airlines Logo
5:40 pm - 1:35 pmYYT-ORD
22h 25m2 stops
$471Multiple Airlines
Find Deal
Sun, Nov 16 - Sun, Nov 23
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
Porter Airlines Logo
6:20 am - 3:20 pmYYT-MDW
11h 30m2 stops
$491Porter Airlines
Find Deal
Sun, Nov 16 - Sun, Nov 23
Porter Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m2 stops
$506Porter Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
Multiple Airlines Logo
3:26 pm - 1:01 amORD-YYT
31h 05m3 stops
Multiple Airlines Logo
5:40 pm - 11:29 pmYYT-ORD
32h 19m2 stops
$553Multiple Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
Porter Airlines Logo
11:00 am - 11:15 pmMDW-YYT
9h 45m2 stops
Porter Airlines Logo
6:00 am - 3:20 pmYYT-MDW
11h 50m2 stops
$557Porter Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Air Canada Logo
10:40 am - 11:55 pmORD-YDF
10h 45m2 stops
Air Canada Logo
6:50 pm - 3:10 pmYDF-ORD
22h 50m2 stops
$561Air Canada
Find Deal
Fri, Oct 24 - Fri, Nov 7
Air Canada Logo
3:35 pm - 12:56 amORD-YYT
6h 51m1 stop
Air Canada Logo
7:30 am - 2:55 pmYYT-ORD
9h 55m2 stops
$581Air Canada
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Fri, Dec 12 - Mon, Dec 15
United Airlines Logo
1:00 pm - 1:36 amORD-YYT
10h 06m2 stops
United Airlines Logo
5:05 am - 11:18 amYYT-ORD
8h 43m1 stop
$656United Airlines
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Sat, Nov 15 - Sat, Nov 22
United Airlines Logo
3:35 pm - 12:56 amORD-YYT
6h 51m1 stop
United Airlines Logo
5:05 am - 2:11 pmYYT-ORD
11h 36m2 stops
$661United Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21

Porter Airlines flights from Chicago to Newfoundland and Labrador

Our best Porter Airlines deals on Chicago to Newfoundland and Labrador flight tickets
Porter Airlines
Nov 16
MDW11:00 amChicago Midway
11h 31m
2 stops
YYT1:01 amSt John's
Nov 23
YYT6:20 amSt John's
11h 30m
2 stops
MDW3:20 pmChicago Midway
$491
Find similar
Porter Airlines
Nov 14
MDW11:00 amChicago Midway
11h 31m
2 stops
YYT1:01 amSt John's
Nov 21
YYT6:00 amSt John's
11h 50m
2 stops
MDW3:20 pmChicago Midway
$506
Find similar
Porter Airlines
Dec 12
MDW11:00 amChicago Midway
9h 45m
2 stops
YYT11:15 pmSt John's
Dec 15
YYT6:00 amSt John's
11h 50m
2 stops
MDW3:20 pmChicago Midway
$557
Find similar

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 24
ORD10:40 amChicago O'Hare Intl
10h 45m
2 stops
YDF11:55 pmDeer Lake
Nov 7
YDF6:50 pmDeer Lake
22h 50m
2 stops
ORD3:10 pmChicago O'Hare Intl
$561
Find similar
Air Canada
Dec 12
ORD3:35 pmChicago O'Hare Intl
6h 51m
1 stop
YYT12:56 amSt John's
Dec 15
YYT7:30 amSt John's
9h 55m
2 stops
ORD2:55 pmChicago O'Hare Intl
$581
Find similar
Air Canada
Dec 12
ORD2:00 pmChicago O'Hare Intl
8h 26m
2 stops
YYT12:56 amSt John's
Dec 15
YYT7:30 amSt John's
9h 55m
2 stops
ORD2:55 pmChicago O'Hare Intl
$588
Find similar

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 832,500 searches. Data last updated October 2, 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

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 11/15

6:48 am-1:01 am

2 stops15h 43m

St John's

Sat 11/22

6:00 am-10:39 am

3 stops31h 09m

$441

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sun 11/16

5:25 am-2:28 pm

1 stop30h 33m

St John's

Sun 11/23

5:40 pm-1:35 pm

2 stops22h 25m

$471

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sun 11/16

11:00 am-1:01 am

2 stops11h 31m

St John's

Sun 11/23

6:20 am-3:20 pm

2 stops11h 30m

$491

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 11/14

11:00 am-1:01 am

2 stops11h 31m

St John's

Fri 11/21

6:00 am-3:20 pm

2 stops11h 50m

$506

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 11/14

3:26 pm-1:01 am

3 stops31h 05m

St John's

Fri 11/21

5:40 pm-11:29 pm

2 stops32h 19m

$553

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 12/12

11:00 am-11:15 pm

2 stops9h 45m

St John's

Mon 12/15

6:00 am-3:20 pm

2 stops11h 50m

$557

ChicagoDeer Lake

ORD - YDF

ORDYDF

Chicago O'Hare Intl

Fri 10/24

10:40 am-11:55 pm

2 stops10h 45m

Deer Lake

Fri 11/7

6:50 pm-3:10 pm

2 stops22h 50m

$561

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 12/12

3:35 pm-12:56 am

1 stop6h 51m

St John's

Mon 12/15

7:30 am-2:55 pm

2 stops9h 55m

$581

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 11/15

1:00 pm-1:36 am

2 stops10h 06m

St John's

Sat 11/22

5:05 am-11:18 am

1 stop8h 43m

$656

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 11/14

3:35 pm-12:56 am

1 stop6h 51m

St John's

Fri 11/21

5:05 am-2:11 pm

2 stops11h 36m

$661

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 day to depart on your flight to Newfoundland and Labrador?

Our data shows that Saturday is the least expensive day to fly to Newfoundland and Labrador. Tickets to fly out on this day can be as low as $593. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Newfoundland and Labrador on Friday is $842.

What is the cheapest time of day to depart on your flight to Newfoundland and Labrador?

Flying to Newfoundland and Labrador from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $609 when looking at flights departing in the afternoon. Flights to Newfoundland and Labrador are more costly in the morning, with an average ticket price of $699. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

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

Direct flights

None
There are no direct flights from Chicago to Newfoundland and Labrador. There are no popular flight routes from Chicago to Newfoundland and Labrador.
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  • 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?

  • 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 CanadaPriceFrom $331Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
United AirlinesPriceFrom $489Free CancellationRating
7.4
8,933 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.

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