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Cheap flights from Newfoundland and Labrador to Chicago from C$ 318

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 21/9. 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

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  St John's-MDW Chicago Midway
11h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
3:20 p.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
7h 05m2 stops Toronto Island Ottawa
C$ 727Porter Airlines
Fri, 18 Sep - Mon, 21 Sep
American Airlines Logo
10:00 a.m. - 4:19 p.m.YYT  St John's-ORD Chicago O'Hare Intl
8h 49m1 stop Toronto Pearson Intl
American Airlines Logo
8:03 a.m. - 6:05 p.m.ORD  Chicago O'Hare Intl-YYT St John's
7h 32m1 stop Toronto Pearson Intl
C$ 746American Airlines
Fri, 4 Sep - Sat, 12 Sep
Air Canada Logo
5:30 a.m. - 10:15 a.m.YYT  St John's-ORD Chicago O'Hare Intl
7h 15m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:40 p.m. - 12:33 a.m.ORD  Chicago O'Hare Intl-YYT St John's
6h 23m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 747Air Canada
Fri, 18 Sep - Mon, 21 Sep
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
11:45 a.m. - 10:55 p.m.MDW  Chicago Midway-YYT St John's
32h 40m2 stops Toronto Island Montreal St Hubert
C$ 749Porter Airlines
Fri, 18 Sep - Sun, 20 Sep
Air Canada Logo
5:30 a.m. - 10:15 a.m.YYT  St John's-ORD Chicago O'Hare Intl
7h 15m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 5:08 p.m.ORD  Chicago O'Hare Intl-YYT St John's
5h 53m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 752Air Canada
Fri, 18 Sep - Sun, 20 Sep
Porter Airlines Logo
6:05 a.m. - 2:20 p.m.YYT  St John's-ORD Chicago O'Hare Intl
10h 45m2 stops Ottawa Toronto Pearson Intl
Porter Airlines Logo
8:03 a.m. - 6:05 p.m.ORD  Chicago O'Hare Intl-YYT St John's
7h 32m1 stop Toronto Pearson Intl
C$ 791Porter Airlines
Tue, 22 Sep - Sat, 26 Sep
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
C$ 792Porter Airlines
Tue, 22 Sep - Sat, 26 Sep
Porter Airlines Logo
6:05 a.m. - 2:20 p.m.YYT  St John's-ORD Chicago O'Hare Intl
10h 45m2 stops Ottawa Toronto Pearson Intl
Porter Airlines Logo
8:03 a.m. - 6:05 p.m.ORD  Chicago O'Hare Intl-YYT St John's
7h 32m1 stop Toronto Pearson Intl
C$ 793Porter Airlines
Tue, 22 Sep - Sat, 26 Sep
Porter Airlines Logo
6:05 a.m. - 2:20 p.m.YYT  St John's-ORD Chicago O'Hare Intl
10h 45m2 stops Ottawa Toronto Pearson Intl
Porter Airlines Logo
8:03 a.m. - 6:05 p.m.ORD  Chicago O'Hare Intl-YYT St John's
7h 32m1 stop Toronto Pearson Intl
C$ 809Porter Airlines
Tue, 22 Sep - Sat, 26 Sep
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
3:20 p.m. - 10:55 p.m.MDW  Chicago Midway-YYT St John's
29h 05m2 stops Toronto Island Montreal St Hubert
C$ 838Porter Airlines
Sat, 26 Sep - Tue, 29 Sep

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WestJet flights from Newfoundland and Labrador to Chicago

Our best WestJet deals on Newfoundland and Labrador to Chicago flight tickets
WestJet
4 Sep
YYT3:00 p.m.St John's
28h 21m
2 stops
ORD4:51 p.m.Chicago O'Hare Intl
12 Sep
ORD6:00 p.m.Chicago O'Hare Intl
26h 25m
2 stops
YYT10:55 p.m.St John's
C$ 922
WestJet
21 Aug
YYT3:00 p.m.St John's
27h 00m
2 stops
ORD3:30 p.m.Chicago O'Hare Intl
24 Aug
ORD7:05 a.m.Chicago O'Hare Intl
13h 20m
2 stops
YYT10:55 p.m.St John's
C$ 1,442

American Airlines flights from Newfoundland and Labrador to Chicago

Our best American Airlines deals on Newfoundland and Labrador to Chicago flight tickets
American Airlines
4 Sep
YYT10:00 a.m.St John's
8h 49m
1 stop
ORD4:19 p.m.Chicago O'Hare Intl
12 Sep
ORD8:03 a.m.Chicago O'Hare Intl
7h 32m
1 stop
YYT6:05 p.m.St John's
C$ 746
American Airlines
21 Aug
YYT10:00 a.m.St John's
24h 29m
2 stops
ORD7:59 a.m.Chicago O'Hare Intl
24 Aug
ORD8:05 a.m.Chicago O'Hare Intl
13h 00m
3 stops
YYT11:35 p.m.St John's
C$ 1,725
American Airlines
21 Aug
YYT10:00 a.m.St John's
28h 45m
2 stops
ORD12:15 p.m.Chicago O'Hare Intl
24 Aug
ORD8:05 a.m.Chicago O'Hare Intl
13h 00m
3 stops
YYT11:35 p.m.St John's
C$ 2,081

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 10 August 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 St John's - MDW Chicago Midway

YYTMDW

St John's

Fri 18/9

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

2 stops11h 00m

Chicago Midway

Mon 21/9

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

2 stops7h 05m

C$ 727

St. John'sChicago

YYT St John's - ORD Chicago O'Hare Intl

YYTORD

St John's

Fri 4/9

10:00 a.m.-4:19 p.m.

1 stop8h 49m

Chicago O'Hare Intl

Sat 12/9

8:03 a.m.-6:05 p.m.

1 stop7h 32m

C$ 746

St. John'sChicago

YYT St John's - ORD Chicago O'Hare Intl

YYTORD

St John's

Fri 18/9

5:30 a.m.-10:15 a.m.

1 stop7h 15m

Chicago O'Hare Intl

Mon 21/9

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

1 stop6h 23m

C$ 747

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Fri 18/9

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

2 stops11h 00m

Chicago Midway

Sun 20/9

11:45 a.m.-10:55 p.m.

2 stops32h 40m

C$ 749
Quickest round-trip

St. John'sChicago

YYT St John's - ORD Chicago O'Hare Intl

YYTORD

St John's

Fri 18/9

5:30 a.m.-10:15 a.m.

1 stop7h 15m

Chicago O'Hare Intl

Sun 20/9

8:45 a.m.-5:08 p.m.

1 stop5h 53m

C$ 752

St. John'sChicago

YYT St John's - ORD Chicago O'Hare Intl

YYTORD

St John's

Tue 22/9

6:05 a.m.-2:20 p.m.

2 stops10h 45m

Chicago O'Hare Intl

Sat 26/9

8:03 a.m.-6:05 p.m.

1 stop7h 32m

C$ 791

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Tue 22/9

6:00 a.m.-2:35 p.m.

2 stops11h 05m

Chicago Midway

Sat 26/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

C$ 792

St. John'sChicago

YYT St John's - ORD Chicago O'Hare Intl

YYTORD

St John's

Tue 22/9

6:05 a.m.-2:20 p.m.

2 stops10h 45m

Chicago O'Hare Intl

Sat 26/9

8:03 a.m.-6:05 p.m.

1 stop7h 32m

C$ 793

St. John'sChicago

YYT St John's - ORD Chicago O'Hare Intl

YYTORD

St John's

Tue 22/9

6:05 a.m.-2:20 p.m.

2 stops10h 45m

Chicago O'Hare Intl

Sat 26/9

8:03 a.m.-6:05 p.m.

1 stop7h 32m

C$ 809

St. John'sChicago

YYT St John's - MDW Chicago Midway

YYTMDW

St John's

Sat 26/9

6:00 a.m.-2:35 p.m.

2 stops11h 05m

Chicago Midway

Tue 29/9

3:20 p.m.-10:55 p.m.

2 stops29h 05m

C$ 838

Flights are sorted by cheapest round-trip flights first.

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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 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

7h 52m

Direct flights

None
The fastest flight from Newfoundland and Labrador to Chicago takes 7h 52m
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
Valparaiso
Portage

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