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Cheap flights from Newfoundland and Labrador to Chicago from C$ 362

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Newfoundland and Labrador to Chicago departing on 11/4. 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 Newfoundland and Labrador to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
5:05 a.m. - 11:18 a.m.YYT-ORD
8h 43m1 stop
Air Canada Logo
7:05 a.m. - 5:21 p.m.ORD-YYT
7h 46m1 stop
C$ 642Air Canada
Find Deal
Thu, 4 Dec - Thu, 11 Dec
Air Canada Logo
5:05 a.m. - 11:18 a.m.YYT-ORD
8h 43m1 stop
Air Canada Logo
10:00 a.m. - 11:30 p.m.ORD-YYT
11h 00m2 stops
C$ 646Air Canada
Find Deal
Thu, 4 Dec - Thu, 11 Dec
Air Canada Logo
5:05 a.m. - 1:01 p.m.YYT-ORD
10h 26m2 stops
Air Canada Logo
8:00 a.m. - 8:15 p.m.ORD-YYT
9h 45m2 stops
C$ 653Air Canada
Find Deal
Thu, 4 Dec - Thu, 11 Dec
Porter Airlines Logo
6:20 a.m. - 3:20 p.m.YYT-MDW
11h 30m2 stops
Porter Airlines Logo
4:15 p.m. - 4:45 p.m.MDW-YYT
22h 00m1 stop
C$ 681Porter Airlines
Find Deal
Thu, 4 Dec - Thu, 11 Dec
Air Canada Logo
6:35 a.m. - 1:01 p.m.YYT-ORD
8h 56m1 stop
Air Canada Logo
7:15 a.m. - 5:21 p.m.ORD-YYT
7h 36m1 stop
C$ 684Air Canada
Find Deal
Wed, 31 Dec - Tue, 6 Jan
Air Canada Logo
5:05 a.m. - 3:10 p.m.YYT-ORD
12h 35m2 stops
Air Canada Logo
7:15 a.m. - 8:15 p.m.ORD-YYT
10h 30m2 stops
C$ 685Air Canada
Find Deal
Wed, 31 Dec - Tue, 6 Jan
Air Canada Logo
5:05 a.m. - 3:10 p.m.YYT-ORD
12h 35m2 stops
Air Canada Logo
7:15 a.m. - 8:15 p.m.ORD-YYT
10h 30m2 stops
C$ 686Air Canada
Find Deal
Wed, 31 Dec - Tue, 6 Jan
Multiple Airlines Logo
3:35 p.m. - 4:03 p.m.YYT-ORD
26h 58m1 stop
Multiple Airlines Logo
7:20 a.m. - 1:03 a.m.ORD-YYT
15h 13m2 stops
C$ 727Multiple Airlines
Find Deal
Mon, 1 Dec - Mon, 8 Dec
Porter Airlines Logo
6:20 a.m. - 3:20 p.m.YYT-MDW
11h 30m2 stops
Porter Airlines Logo
4:15 p.m. - 1:03 a.m.MDW-YYT
30h 18m2 stops
C$ 851Porter Airlines
Find Deal
Mon, 1 Dec - Mon, 8 Dec
Porter Airlines Logo
5:40 p.m. - 7:15 a.m.YYT-ORD
16h 05m1 stop
Porter Airlines Logo
6:34 p.m. - 11:15 p.m.ORD-YYT
26h 11m2 stops
C$ 893Porter Airlines
Find Deal
Mon, 1 Dec - Mon, 8 Dec

Air Canada flights from Newfoundland and Labrador to Chicago

Our best Air Canada deals on Newfoundland and Labrador to Chicago flight tickets
Air Canada
4 Dec
YYT5:05 a.m.St John's
8h 43m
1 stop
ORD11:18 a.m.Chicago O'Hare Intl
11 Dec
ORD7:05 a.m.Chicago O'Hare Intl
7h 46m
1 stop
YYT5:21 p.m.St John's
C$ 642
Find similar
Air Canada
4 Dec
YYT5:05 a.m.St John's
8h 43m
1 stop
ORD11:18 a.m.Chicago O'Hare Intl
11 Dec
ORD10:00 a.m.Chicago O'Hare Intl
11h 00m
2 stops
YYT11:30 p.m.St John's
C$ 646
Find similar
Air Canada
4 Dec
YYT5:05 a.m.St John's
10h 26m
2 stops
ORD1:01 p.m.Chicago O'Hare Intl
11 Dec
ORD8:00 a.m.Chicago O'Hare Intl
9h 45m
2 stops
YYT8:15 p.m.St John's
C$ 653
Find similar

Porter Airlines flights from Newfoundland and Labrador to Chicago

Our best Porter Airlines deals on Newfoundland and Labrador to Chicago flight tickets
Porter Airlines
4 Dec
YYT6:20 a.m.St John's
11h 30m
2 stops
MDW3:20 p.m.Chicago Midway
11 Dec
MDW4:15 p.m.Chicago Midway
22h 00m
1 stop
YYT4:45 p.m.St John's
C$ 681
Find similar
Porter Airlines
1 Dec
YYT6:20 a.m.St John's
11h 30m
2 stops
MDW3:20 p.m.Chicago Midway
8 Dec
MDW4:15 p.m.Chicago Midway
30h 18m
2 stops
YYT1:03 a.m.St John's
C$ 851
Find similar
Porter Airlines
1 Dec
YYT5:40 p.m.St John's
16h 05m
1 stop
ORD7:15 a.m.Chicago O'Hare Intl
8 Dec
ORD6:34 p.m.Chicago O'Hare Intl
26h 11m
2 stops
YYT11:15 p.m.St John's
C$ 893
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Newfoundland and Labrador to Chicago 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 96,600 searches. Data last updated 4 November 2025.
Use the filters below to find and compare flights from Newfoundland and Labrador to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 4/12

5:05 a.m.-11:18 a.m.

1 stop8h 43m

Chicago O'Hare Intl

Thu 11/12

7:05 a.m.-5:21 p.m.

1 stop7h 46m

C$ 642

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 4/12

5:05 a.m.-11:18 a.m.

1 stop8h 43m

Chicago O'Hare Intl

Thu 11/12

10:00 a.m.-11:30 p.m.

2 stops11h 00m

C$ 646

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 4/12

5:05 a.m.-1:01 p.m.

2 stops10h 26m

Chicago O'Hare Intl

Thu 11/12

8:00 a.m.-8:15 p.m.

2 stops9h 45m

C$ 653

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/12

6:20 a.m.-3:20 p.m.

2 stops11h 30m

Chicago Midway

Thu 11/12

4:15 p.m.-4:45 p.m.

1 stop22h 00m

C$ 681

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 31/12

6:35 a.m.-1:01 p.m.

1 stop8h 56m

Chicago O'Hare Intl

Tue 6/1

7:15 a.m.-5:21 p.m.

1 stop7h 36m

C$ 684

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 31/12

5:05 a.m.-3:10 p.m.

2 stops12h 35m

Chicago O'Hare Intl

Tue 6/1

7:15 a.m.-8:15 p.m.

2 stops10h 30m

C$ 685

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 31/12

5:05 a.m.-3:10 p.m.

2 stops12h 35m

Chicago O'Hare Intl

Tue 6/1

7:15 a.m.-8:15 p.m.

2 stops10h 30m

C$ 686

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 1/12

3:35 p.m.-4:03 p.m.

1 stop26h 58m

Chicago O'Hare Intl

Mon 8/12

7:20 a.m.-1:03 a.m.

2 stops15h 13m

C$ 727

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Mon 1/12

6:20 a.m.-3:20 p.m.

2 stops11h 30m

Chicago Midway

Mon 8/12

4:15 p.m.-1:03 a.m.

2 stops30h 18m

C$ 851

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 1/12

5:40 p.m.-7:15 a.m.

1 stop16h 05m

Chicago O'Hare Intl

Mon 8/12

6:34 p.m.-11:15 p.m.

2 stops26h 11m

C$ 893

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Chicago from

How to get the cheapest flight ticket from Newfoundland and Labrador to Chicago

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 Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 714. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 887. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the morning is the cheapest time of day to fly from Newfoundland and Labrador to Chicago when you can find flight prices for as low as C$ 714. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 840 per ticket.

Cheap Newfoundland and Labrador to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Newfoundland and Labrador to Chicago

Direct flights

None
There are no direct flights from Newfoundland and Labrador to Chicago. There are no popular flight routes from Newfoundland and Labrador to Chicago.
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  • When did momondo last update prices for flights from Newfoundland and Labrador to Chicago?

    Prices for flights from Newfoundland and Labrador to Chicago are updated daily.

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

  • How old do you have to be to fly from Newfoundland and Labrador to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Newfoundland and Labrador to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago 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 Newfoundland and Labrador to Chicago

Compare and see reviews for airlines that fly from Newfoundland and Labrador to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 694Free CancellationRating
7.1
10,398 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

It is quick and easy to find Newfoundland and Labrador to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo allows you to filter the results for Newfoundland and Labrador to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search for Newfoundland and Labrador to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Chicago from Newfoundland and Labrador. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport