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Cheap flights from Newfoundland and Labrador to Chicago from C$ 364

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 21/6. 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
2:05 p.m. - 7:48 p.m.
YDF
-
ORD
8h 13m
1 stop
Air Canada Logo
8:45 a.m. - 4:34 p.m.
ORD
-
YDF
5h 19m
1 stop
C$ 716Air Canada
Sat, 26 Sep - Wed, 30 Sep
Air Canada Logo
5:35 a.m. - 10:17 a.m.
YYT
-
ORD
7h 12m
1 stop
Air Canada Logo
3:40 p.m. - 12:33 a.m.
ORD
-
YYT
6h 23m
1 stop
C$ 719Air Canada
Wed, 23 Sep - Sat, 26 Sep
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$ 744Air Canada
Thu, 27 Aug - Mon, 31 Aug
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$ 745Air Canada
Sat, 25 Jul - Mon, 27 Jul
Air Canada Logo
5:35 a.m. - 1:10 p.m.
YYT
-
ORD
10h 05m
2 stops
Air Canada Logo
8:45 a.m. - 11:28 p.m.
ORD
-
YYT
12h 13m
2 stops
C$ 750Air Canada
Mon, 31 Aug - Thu, 3 Sep
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:15 a.m. - 12:56 a.m.
MDW
-
YYT
12h 11m
2 stops
C$ 812Porter Airlines
Tue, 26 May - Tue, 2 Jun
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:15 a.m. - 12:56 a.m.
MDW
-
YYT
12h 11m
2 stops
C$ 929Porter Airlines
Tue, 26 May - Tue, 2 Jun
Delta Logo
3:00 p.m. - 1:11 p.m.
YYT
-
MDW
24h 41m
2 stops
Delta Logo
5:59 p.m. - 10:55 p.m.
MDW
-
YYT
26h 26m
2 stops
C$ 1,145Delta
Tue, 15 Sep - Sat, 19 Sep
Delta Logo
3:00 p.m. - 8:38 a.m.
YYT
-
MDW
20h 08m
2 stops
Delta Logo
5:59 p.m. - 10:55 p.m.
MDW
-
YYT
26h 26m
2 stops
C$ 1,158Delta
Tue, 15 Sep - Sat, 19 Sep
Delta Logo
3:00 p.m. - 1:11 p.m.
YYT
-
MDW
24h 41m
2 stops
Delta Logo
5:59 p.m. - 10:55 p.m.
MDW
-
YYT
26h 26m
2 stops
C$ 1,159Delta
Tue, 15 Sep - Sat, 19 Sep

United Airlines flights from Newfoundland and Labrador to Chicago

Our best United Airlines deals on Newfoundland and Labrador to Chicago flight tickets
United Airlines
25 Jul
YDF5:00 a.m.Deer Lake
19h 36m
2 stops
ORD10:06 p.m.Chicago O'Hare Intl
27 Jul
ORD7:10 a.m.Chicago O'Hare Intl
6h 55m
1 stop
YDF4:35 p.m.Deer Lake
C$ 905
United Airlines
27 Aug
YDF2:25 p.m.Deer Lake
11h 21m
2 stops
ORD11:16 p.m.Chicago O'Hare Intl
31 Aug
ORD10:50 a.m.Chicago O'Hare Intl
11h 37m
2 stops
YDF12:57 a.m.Deer Lake
C$ 912
United Airlines
27 Aug
YDF5:00 a.m.Deer Lake
12h 06m
2 stops
ORD2:36 p.m.Chicago O'Hare Intl
31 Aug
ORD10:50 a.m.Chicago O'Hare Intl
11h 37m
2 stops
YDF12:57 a.m.Deer Lake
C$ 913

Air Canada flights from Newfoundland and Labrador to Chicago

Our best Air Canada deals on Newfoundland and Labrador to Chicago flight tickets
Air Canada
26 Sep
YDF2:05 p.m.Deer Lake
8h 13m
1 stop
ORD7:48 p.m.Chicago O'Hare Intl
30 Sep
ORD8:45 a.m.Chicago O'Hare Intl
5h 19m
1 stop
YDF4:34 p.m.Deer Lake
C$ 716
Air Canada
27 Aug
YDF5:00 a.m.Deer Lake
6h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
31 Aug
ORD8:45 a.m.Chicago O'Hare Intl
5h 20m
1 stop
YDF4:35 p.m.Deer Lake
C$ 744
Air Canada
25 Jul
YDF5:00 a.m.Deer Lake
6h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
27 Jul
ORD8:45 a.m.Chicago O'Hare Intl
5h 20m
1 stop
YDF4:35 p.m.Deer Lake
C$ 745

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 9 May 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

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sat 26/9

2:05 p.m.-7:48 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Wed 30/9

8:45 a.m.-4:34 p.m.

1 stop5h 19m

C$ 716

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 23/9

5:35 a.m.-10:17 a.m.

1 stop7h 12m

Chicago O'Hare Intl

Sat 26/9

3:40 p.m.-12:33 a.m.

1 stop6h 23m

C$ 719
Quickest round-trip

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Thu 27/8

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

1 stop6h 30m

Chicago O'Hare Intl

Mon 31/8

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

1 stop5h 20m

C$ 744

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Sat 25/7

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

1 stop6h 30m

Chicago O'Hare Intl

Mon 27/7

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

1 stop5h 20m

C$ 745

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

8:45 a.m.-11:28 p.m.

2 stops12h 13m

C$ 750

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

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

2 stops11h 00m

Chicago Midway

Tue 2/6

10:15 a.m.-12:56 a.m.

2 stops12h 11m

C$ 812

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

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

2 stops11h 00m

Chicago Midway

Tue 2/6

10:15 a.m.-12:56 a.m.

2 stops12h 11m

C$ 929

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-1:11 p.m.

2 stops24h 41m

Chicago Midway

Sat 19/9

5:59 p.m.-10:55 p.m.

2 stops26h 26m

C$ 1,145

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-8:38 a.m.

2 stops20h 08m

Chicago Midway

Sat 19/9

5:59 p.m.-10:55 p.m.

2 stops26h 26m

C$ 1,158

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-1:11 p.m.

2 stops24h 41m

Chicago Midway

Sat 19/9

5:59 p.m.-10:55 p.m.

2 stops26h 26m

C$ 1,159

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, United Airlines, and Air Canada 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

8h 16m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago takes 8h 16m
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