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Cheap flights from Newfoundland and Labrador to Chicago from C$ 389

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 3/9. 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

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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
5:00 a.m. - 9:00 a.m.
YDF
-
ORD
6h 30m
1 stop
Air Canada Logo
3:45 p.m. - 12:57 a.m.
ORD
-
YDF
6h 42m
1 stop
C$ 719Air Canada
Fri, 4 Sep - Mon, 7 Sep
Air Canada Logo
6:35 a.m. - 1:05 p.m.
YYT
-
ORD
9h 00m
1 stop
Air Canada Logo
9:50 a.m. - 11:28 p.m.
ORD
-
YYT
11h 08m
2 stops
C$ 739Air Canada
Sat, 18 Apr - Wed, 22 Apr
Porter Airlines Logo
6:00 a.m. - 12:10 p.m.
YYT
-
MDW
8h 40m
2 stops
Porter Airlines Logo
11:00 a.m. - 11:05 p.m.
MDW
-
YYT
9h 35m
2 stops
C$ 743Porter Airlines
Sat, 18 Apr - Wed, 22 Apr
Air Canada Logo
5:25 a.m. - 1:05 p.m.
YYT
-
ORD
10h 10m
2 stops
Air Canada Logo
9:50 a.m. - 11:28 p.m.
ORD
-
YYT
11h 08m
2 stops
C$ 743Air Canada
Sat, 18 Apr - Wed, 22 Apr
United Airlines Logo
5:35 a.m. - 11:20 a.m.
YYT
-
ORD
8h 15m
1 stop
United Airlines Logo
6:30 a.m. - 12:36 a.m.
ORD
-
YYT
15h 36m
2 stops
C$ 752United Airlines
Sat, 23 May - Wed, 3 Jun
Porter Airlines Logo
6:00 a.m. - 12:10 p.m.
YYT
-
MDW
8h 40m
2 stops
Porter Airlines Logo
11:00 a.m. - 11:05 p.m.
MDW
-
YYT
9h 35m
2 stops
C$ 754Porter Airlines
Sat, 18 Apr - Wed, 22 Apr
Air Canada Logo
6:35 a.m. - 1:05 p.m.
YYT
-
ORD
9h 00m
1 stop
Air Canada Logo
8:40 a.m. - 5:21 p.m.
ORD
-
YYT
6h 11m
1 stop
C$ 759Air Canada
Sat, 18 Apr - Wed, 22 Apr
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:25 a.m. - 12:56 a.m.
MDW
-
YYT
12h 01m
2 stops
C$ 759Porter Airlines
Tue, 26 May - Fri, 29 May
United Airlines Logo
2:05 p.m. - 11:26 p.m.
YYT
-
ORD
11h 51m
2 stops
United Airlines Logo
11:03 a.m. - 12:36 a.m.
ORD
-
YYT
11h 03m
2 stops
C$ 761United Airlines
Sat, 23 May - Wed, 3 Jun
Air Canada Logo
5:25 a.m. - 3:15 p.m.
YYT
-
ORD
12h 20m
2 stops
Air Canada Logo
8:40 a.m. - 5:21 p.m.
ORD
-
YYT
6h 11m
1 stop
C$ 763Air Canada
Sat, 18 Apr - Wed, 22 Apr

Air Canada flights from Newfoundland and Labrador to Chicago

Our best Air Canada deals on Newfoundland and Labrador to Chicago flight tickets
Air Canada
5 May
YYT2:00 p.m.St John's
8h 38m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
6 May
ORD8:45 a.m.Chicago O'Hare Intl
8h 28m
2 stops
YYT7:43 p.m.St John's
C$ 725
Air Canada
5 May
YYT5:35 a.m.St John's
10h 20m
2 stops
ORD1:25 p.m.Chicago O'Hare Intl
6 May
ORD8:45 a.m.Chicago O'Hare Intl
8h 28m
2 stops
YYT7:43 p.m.St John's
C$ 736
Air Canada
5 May
YYT2:00 p.m.St John's
8h 38m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
6 May
ORD8:45 a.m.Chicago O'Hare Intl
5h 56m
1 stop
YYT5:11 p.m.St John's
C$ 756

United Airlines flights from Newfoundland and Labrador to Chicago

Our best United Airlines deals on Newfoundland and Labrador to Chicago flight tickets
United Airlines
23 May
YYT5:35 a.m.St John's
8h 15m
1 stop
ORD11:20 a.m.Chicago O'Hare Intl
3 Jun
ORD6:30 a.m.Chicago O'Hare Intl
15h 36m
2 stops
YYT12:36 a.m.St John's
C$ 752
United Airlines
23 May
YYT2:05 p.m.St John's
11h 51m
2 stops
ORD11:26 p.m.Chicago O'Hare Intl
3 Jun
ORD11:03 a.m.Chicago O'Hare Intl
11h 03m
2 stops
YYT12:36 a.m.St John's
C$ 761
United Airlines
23 May
YYT5:35 a.m.St John's
7h 13m
1 stop
ORD10:18 a.m.Chicago O'Hare Intl
3 Jun
ORD9:55 a.m.Chicago O'Hare Intl
13h 23m
1 stop
YYT1:48 a.m.St John's
C$ 810

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 25 March 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
Quickest round-trip

Deer LakeChicago

YDF - ORD

YDFORD

Deer Lake

Fri 4/9

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

1 stop6h 30m

Chicago O'Hare Intl

Mon 7/9

3:45 p.m.-12:57 a.m.

1 stop6h 42m

C$ 719

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 18/4

6:35 a.m.-1:05 p.m.

1 stop9h 00m

Chicago O'Hare Intl

Wed 22/4

9:50 a.m.-11:28 p.m.

2 stops11h 08m

C$ 739

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 18/4

6:00 a.m.-12:10 p.m.

2 stops8h 40m

Chicago Midway

Wed 22/4

11:00 a.m.-11:05 p.m.

2 stops9h 35m

C$ 743

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 18/4

5:25 a.m.-1:05 p.m.

2 stops10h 10m

Chicago O'Hare Intl

Wed 22/4

9:50 a.m.-11:28 p.m.

2 stops11h 08m

C$ 743

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 23/5

5:35 a.m.-11:20 a.m.

1 stop8h 15m

Chicago O'Hare Intl

Wed 3/6

6:30 a.m.-12:36 a.m.

2 stops15h 36m

C$ 752

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 18/4

6:00 a.m.-12:10 p.m.

2 stops8h 40m

Chicago Midway

Wed 22/4

11:00 a.m.-11:05 p.m.

2 stops9h 35m

C$ 754

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 18/4

6:35 a.m.-1:05 p.m.

1 stop9h 00m

Chicago O'Hare Intl

Wed 22/4

8:40 a.m.-5:21 p.m.

1 stop6h 11m

C$ 759

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

Fri 29/5

10:25 a.m.-12:56 a.m.

2 stops12h 01m

C$ 759

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 23/5

2:05 p.m.-11:26 p.m.

2 stops11h 51m

Chicago O'Hare Intl

Wed 3/6

11:03 a.m.-12:36 a.m.

2 stops11h 03m

C$ 761

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 18/4

5:25 a.m.-3:15 p.m.

2 stops12h 20m

Chicago O'Hare Intl

Wed 22/4

8:40 a.m.-5:21 p.m.

1 stop6h 11m

C$ 763

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?

Air Canada, United Airlines, and Porter 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

6h 30m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago takes 6h 30m
There are no direct flights from Newfoundland and Labrador to Chicago. There are no popular flight routes from Newfoundland and Labrador to Chicago.
Search flight deals

  • 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
Munster
Hammond

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