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Cheap flights from Newfoundland and Labrador to Chicago from C$ 367

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 10/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Newfoundland and Labrador to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
ORD
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:55 a.m.
ORD
-
YYT
7h 05m
2 stops
C$ 730Porter Airlines
Tue, 15 Sep - Tue, 22 Sep
Air Canada Logo
6:00 a.m. - 1:10 p.m.
YDF
-
ORD
9h 40m
2 stops
Air Canada Logo
7:15 a.m. - 6:59 p.m.
ORD
-
YDF
9h 14m
2 stops
C$ 758Air Canada
Mon, 16 Nov - Tue, 17 Nov
Air Canada Logo
6:00 a.m. - 1:10 p.m.
YDF
-
ORD
9h 40m
2 stops
Air Canada Logo
7:15 a.m. - 6:59 p.m.
ORD
-
YDF
9h 14m
2 stops
C$ 759Air Canada
Mon, 16 Nov - Tue, 17 Nov
Porter Airlines Logo
4:00 p.m. - 11:00 a.m.
YYT
-
ORD
21h 30m
3 stops
Porter Airlines Logo
7:00 a.m. - 10:55 p.m.
ORD
-
YYT
13h 25m
2 stops
C$ 761Porter Airlines
Wed, 16 Sep - Mon, 21 Sep
Air Canada Logo
1:05 p.m. - 8:16 p.m.
YYT
-
ORD
9h 41m
2 stops
Air Canada Logo
2:00 p.m. - 12:56 a.m.
ORD
-
YYT
8h 26m
2 stops
C$ 771Air Canada
Fri, 30 Oct - Mon, 2 Nov
Air Canada Logo
5:00 a.m. - 9:00 a.m.
YDF
-
ORD
6h 30m
1 stop
Air Canada Logo
8:45 a.m. - 4:35 p.m.
ORD
-
YDF
5h 20m
1 stop
C$ 771Air Canada
Sat, 4 Jul - Wed, 8 Jul
WestJet Logo
3:00 p.m. - 9:50 a.m.
YYT
-
MDW
21h 20m
2 stops
WestJet Logo
9:29 a.m. - 10:55 p.m.
MDW
-
YYT
10h 56m
2 stops
C$ 1,057WestJet
Tue, 15 Sep - Sun, 20 Sep
WestJet Logo
3:00 p.m. - 6:19 p.m.
YYT
-
MDW
29h 49m
2 stops
WestJet Logo
9:29 a.m. - 10:55 p.m.
MDW
-
YYT
10h 56m
2 stops
C$ 1,087WestJet
Wed, 16 Sep - Sun, 20 Sep
United Airlines Logo
5:20 p.m. - 2:53 p.m.
YDF
-
ORD
24h 03m
2 stops
United Airlines Logo
2:15 p.m. - 12:57 a.m.
ORD
-
YDF
8h 12m
1 stop
C$ 1,114United Airlines
Mon, 3 Aug - Mon, 10 Aug
United Airlines Logo
5:20 p.m. - 2:53 p.m.
YDF
-
ORD
24h 03m
2 stops
United Airlines Logo
7:00 a.m. - 12:57 a.m.
ORD
-
YDF
15h 27m
2 stops
C$ 1,216United Airlines
Mon, 3 Aug - Mon, 10 Aug

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Air Canada flights from Newfoundland and Labrador to Chicago

Our best Air Canada deals on Newfoundland and Labrador to Chicago flight tickets
Air Canada
16 Nov
YDF6:00 a.m.Deer Lake
9h 40m
2 stops
ORD1:10 p.m.Chicago O'Hare Intl
17 Nov
ORD3:55 p.m.Chicago O'Hare Intl
5h 17m
1 stop
YDF11:42 p.m.Deer Lake
C$ 758
Air Canada
16 Nov
YDF6:00 a.m.Deer Lake
9h 40m
2 stops
ORD1:10 p.m.Chicago O'Hare Intl
17 Nov
ORD7:15 a.m.Chicago O'Hare Intl
9h 14m
2 stops
YDF6:59 p.m.Deer Lake
C$ 759
Air Canada
30 Oct
YYT1:05 p.m.St John's
9h 41m
2 stops
ORD8:16 p.m.Chicago O'Hare Intl
2 Nov
ORD2:00 p.m.Chicago O'Hare Intl
8h 26m
2 stops
YYT12:56 a.m.St John's
C$ 771

Porter Airlines flights from Newfoundland and Labrador to Chicago

Our best Porter Airlines deals on Newfoundland and Labrador to Chicago flight tickets
Porter Airlines
15 Sep
YYT6:05 a.m.St John's
11h 00m
2 stops
ORD2:35 p.m.Chicago O'Hare Intl
22 Sep
ORD3:20 p.m.Chicago O'Hare Intl
7h 05m
2 stops
YYT12:55 a.m.St John's
C$ 730
Porter Airlines
16 Sep
YYT4:00 p.m.St John's
21h 30m
3 stops
ORD11:00 a.m.Chicago O'Hare Intl
21 Sep
ORD7:00 a.m.Chicago O'Hare Intl
13h 25m
2 stops
YYT10:55 p.m.St John's
C$ 761
Porter Airlines
13 Sep
YYT6:05 a.m.St John's
11h 00m
2 stops
ORD2:35 p.m.Chicago O'Hare Intl
22 Sep
ORD3:20 p.m.Chicago O'Hare Intl
7h 05m
2 stops
YYT12:55 a.m.St John's
C$ 774

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 23 June 2026.
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

Cheapest round-trip

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 15/9

6:05 a.m.-2:35 p.m.

2 stops11h 00m

Chicago O'Hare Intl

Tue 22/9

3:20 p.m.-12:55 a.m.

2 stops7h 05m

C$ 730

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Mon 16/11

6:00 a.m.-1:10 p.m.

2 stops9h 40m

Chicago O'Hare Intl

Tue 17/11

7:15 a.m.-6:59 p.m.

2 stops9h 14m

C$ 758

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Mon 16/11

6:00 a.m.-1:10 p.m.

2 stops9h 40m

Chicago O'Hare Intl

Tue 17/11

7:15 a.m.-6:59 p.m.

2 stops9h 14m

C$ 759

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 16/9

4:00 p.m.-11:00 a.m.

3 stops21h 30m

Chicago O'Hare Intl

Mon 21/9

7:00 a.m.-10:55 p.m.

2 stops13h 25m

C$ 761

St. John'sChicago

YYT - ORD

YYTORD

St John's

Fri 30/10

1:05 p.m.-8:16 p.m.

2 stops9h 41m

Chicago O'Hare Intl

Mon 2/11

2:00 p.m.-12:56 a.m.

2 stops8h 26m

C$ 771
Quickest round-trip

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sat 4/7

5:00 a.m.-9:00 a.m.

1 stop6h 30m

Chicago O'Hare Intl

Wed 8/7

8:45 a.m.-4:35 p.m.

1 stop5h 20m

C$ 771

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-9:50 a.m.

2 stops21h 20m

Chicago Midway

Sun 20/9

9:29 a.m.-10:55 p.m.

2 stops10h 56m

C$ 1,057

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 16/9

3:00 p.m.-6:19 p.m.

2 stops29h 49m

Chicago Midway

Sun 20/9

9:29 a.m.-10:55 p.m.

2 stops10h 56m

C$ 1,087

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Mon 3/8

5:20 p.m.-2:53 p.m.

2 stops24h 03m

Chicago O'Hare Intl

Mon 10/8

2:15 p.m.-12:57 a.m.

1 stop8h 12m

C$ 1,114

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Mon 3/8

5:20 p.m.-2:53 p.m.

2 stops24h 03m

Chicago O'Hare Intl

Mon 10/8

7:00 a.m.-12:57 a.m.

2 stops15h 27m

C$ 1,216

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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 airline that flies from Newfoundland and Labrador to Chicago?

Porter Airlines, Air Canada, and United Airlines are the most popular carriers operating from Newfoundland and Labrador to Chicago

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

Fastest flight time

9h 11m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago takes 9h 11m
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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Frequently asked questions about flying from Newfoundland and Labrador to Chicago

  • 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 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.

Travelling to a place near Chicago?

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

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