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Cheap flights from Chicago to Newfoundland and Labrador from $259

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 9/29. 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

Logo
6:30 am - 12:38 amORD-YYT
15h 38m2 stops
Logo
6:00 am - 5:27 pmYYT-ORD
13h 57m2 stops
$442
Find Deal
Wed, Oct 1 - Wed, Oct 8
Porter Airlines Logo
9:35 am - 4:58 pmMDW-YYT
28h 53m2 stops
Porter Airlines Logo
6:25 pm - 8:39 amYYT-MDW
16h 44m1 stop
$480Porter Airlines
Find Deal
Wed, Sep 3 - Thu, Sep 18
Logo
6:30 am - 12:38 amORD-YYT
15h 38m2 stops
Logo
6:00 am - 11:45 pmYYT-ORD
20h 15m3 stops
$482
Find Deal
Wed, Oct 1 - Wed, Oct 8
Porter Airlines Logo
9:35 am - 4:58 pmMDW-YYT
28h 53m2 stops
Porter Airlines Logo
6:00 am - 4:24 pmYYT-MDW
12h 54m1 stop
$495Porter Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 17
Air Canada Logo
3:55 pm - 1:33 amORD-YYT
7h 08m1 stop
Air Canada Logo
5:00 am - 12:05 pmYYT-ORD
9h 35m1 stop
$559Air Canada
Find Deal
Tue, Oct 28 - Tue, Nov 4
Air Canada Logo
3:35 pm - 12:39 amORD-YYT
6h 34m1 stop
Air Canada Logo
2:00 pm - 8:11 pmYYT-ORD
8h 41m1 stop
$572Air Canada
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Sat, Sep 20 - Sat, Sep 27
United Airlines Logo
8:40 am - 5:09 pmORD-YYT
5h 59m1 stop
United Airlines Logo
5:00 am - 6:50 pmYYT-ORD
16h 20m2 stops
$617United Airlines
Find Deal
Tue, Sep 16 - Tue, Sep 23
United Airlines Logo
8:45 am - 12:39 amORD-YYT
13h 24m2 stops
United Airlines Logo
5:00 am - 6:50 pmYYT-ORD
16h 20m2 stops
$621United Airlines
Find Deal
Tue, Sep 16 - Tue, Sep 23
WestJet Logo
10:31 am - 6:20 amMDW-YYT
17h 19m2 stops
WestJet Logo
7:10 am - 9:40 amYYT-MDW
29h 00m2 stops
$1,147WestJet
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Wed, Sep 3 - Mon, Sep 15
WestJet Logo
7:17 pm - 10:56 pmMDW-YYT
25h 09m2 stops
WestJet Logo
7:10 am - 9:40 amYYT-MDW
29h 00m2 stops
$1,227WestJet
Find Deal
Tue, Sep 2 - Mon, Sep 15

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 28
ORD3:55 pmChicago O'Hare Intl
7h 08m
1 stop
YYT1:33 amSt John's
Nov 4
YYT5:00 amSt John's
9h 35m
1 stop
ORD12:05 pmChicago O'Hare Intl
$559
Find similar
Air Canada
Sep 20
ORD3:35 pmChicago O'Hare Intl
6h 34m
1 stop
YYT12:39 amSt John's
Sep 27
YYT2:00 pmSt John's
8h 41m
1 stop
ORD8:11 pmChicago O'Hare Intl
$572
Find similar
Air Canada
Sep 18
ORD12:00 pmChicago O'Hare Intl
7h 11m
1 stop
YYT9:41 pmSt John's
Sep 21
YYT5:50 amSt John's
6h 31m
1 stop
ORD9:51 amChicago O'Hare Intl
$578
Find similar

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 3
MDW9:35 amChicago Midway
28h 53m
2 stops
YYT4:58 pmSt John's
Sep 18
YYT6:25 pmSt John's
16h 44m
1 stop
MDW8:39 amChicago Midway
$480
Find similar
Porter Airlines
Sep 3
MDW9:35 amChicago Midway
28h 53m
2 stops
YYT4:58 pmSt John's
Sep 17
YYT6:00 amSt John's
12h 54m
1 stop
MDW4:24 pmChicago Midway
$495
Find similar
Porter Airlines
Sep 3
MDW9:35 amChicago Midway
28h 53m
2 stops
YYT4:58 pmSt John's
Sep 16
YYT6:00 amSt John's
12h 54m
1 stop
MDW4:24 pmChicago Midway
$532
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 August 18, 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

Wed 10/1

6:30 am-12:38 am

2 stops15h 38m

St John's

Wed 10/8

6:00 am-5:27 pm

2 stops13h 57m

$442

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 9/3

9:35 am-4:58 pm

2 stops28h 53m

St John's

Thu 9/18

6:25 pm-8:39 am

1 stop16h 44m

$480

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 10/1

6:30 am-12:38 am

2 stops15h 38m

St John's

Wed 10/8

6:00 am-11:45 pm

3 stops20h 15m

$482

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 9/3

9:35 am-4:58 pm

2 stops28h 53m

St John's

Wed 9/17

6:00 am-4:24 pm

1 stop12h 54m

$495

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 10/28

3:55 pm-1:33 am

1 stop7h 08m

St John's

Tue 11/4

5:00 am-12:05 pm

1 stop9h 35m

$559

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 9/20

3:35 pm-12:39 am

1 stop6h 34m

St John's

Sat 9/27

2:00 pm-8:11 pm

1 stop8h 41m

$572

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 9/16

8:40 am-5:09 pm

1 stop5h 59m

St John's

Tue 9/23

5:00 am-6:50 pm

2 stops16h 20m

$617

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 9/16

8:45 am-12:39 am

2 stops13h 24m

St John's

Tue 9/23

5:00 am-6:50 pm

2 stops16h 20m

$621

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 9/3

10:31 am-6:20 am

2 stops17h 19m

St John's

Mon 9/15

7:10 am-9:40 am

2 stops29h 00m

$1,147

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Tue 9/2

7:17 pm-10:56 pm

2 stops25h 09m

St John's

Mon 9/15

7:10 am-9:40 am

2 stops29h 00m

$1,227

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest 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

Best Price Found

$259

Fastest flight time

5h 32m

Direct flights

None

Airports in Newfoundland and Labrador

2 airports
The best one-way flight to Newfoundland and Labrador from Chicago in the past 72 hours is $259. The best round-trip flight deal from Chicago to Newfoundland and Labrador found on momondo in the last 72 hours is $442.
The fastest flight from Chicago to Newfoundland and Labrador takes 5h 32m
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, Chicago O'Hare Intl Airport - Deer Lake Airport and Chicago Midway Airport - St John's Airport.
There are 2 airports near Newfoundland and Labrador: St John's (YYT), Deer Lake (YDF)
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?

  • 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
9,992 reviews
Search Air Canada flights
United AirlinesPriceFrom $489Free CancellationRating
7.4
8,925 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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