How does KAYAK find such low prices on flights from Newfoundland and Labrador to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Newfoundland and Labrador to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Newfoundland and Labrador to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Newfoundland and Labrador is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Newfoundland and Labrador to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Newfoundland and Labrador with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Newfoundland and Labrador to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Newfoundland and Labrador up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

C$ 356 CHEAP FLIGHTS from Newfoundland and Labrador to Chicago

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Flight Deals

Cheap Flights from Newfoundland and Labrador to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Newfoundland and Labrador to Chicago

Thu, 1 Oct - Wed, 7 Oct

6:00 a.m. - 11:00 a.m.YYT St John's-MDW Chicago Midway

31h 30m2 stops Montreal St Hubert Toronto Pearson Intl

3:20 p.m. - 10:55 p.m.MDW Chicago Midway-YYT St John's

29h 05m1 stop Toronto Island

C$ 621Multiple Airlines

Thu, 1 Oct - Wed, 7 Oct

6:00 a.m. - 2:55 p.m.YYT St John's-ORD Chicago O'Hare Intl

11h 25m2 stops Montreal St Hubert Toronto Pearson Intl

9:55 a.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YYT St John's

12h 30m2 stops Toronto Pearson Intl Ottawa

C$ 653Multiple Airlines

Thu, 1 Oct - Wed, 7 Oct

7:00 p.m. - 11:00 a.m.YYT St John's-MDW Chicago Midway

18h 30m1 stop Toronto Pearson Intl

3:20 p.m. - 10:55 p.m.MDW Chicago Midway-YYT St John's

29h 05m1 stop Toronto Island

C$ 667Multiple Airlines

Thu, 1 Oct - Wed, 7 Oct

6:00 a.m. - 2:55 p.m.YYT St John's-ORD Chicago O'Hare Intl

11h 25m2 stops Montreal St Hubert Toronto Pearson Intl

8:45 a.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YYT St John's

13h 40m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Island Ottawa

C$ 668Multiple Airlines

Thu, 1 Oct - Wed, 7 Oct

6:00 a.m. - 7:48 p.m.YYT St John's-ORD Chicago O'Hare Intl

16h 18m2 stops Montreal St Hubert Toronto Island

9:55 a.m. - 10:55 p.m.ORD Chicago O'Hare Intl-YYT St John's

10h 30m1 stop Toronto Pearson Intl

C$ 671Multiple Airlines

Thu, 1 Oct - Wed, 7 Oct

6:00 a.m. - 2:35 p.m.YYT St John's-MDW Chicago Midway

11h 05m2 stops Montreal St Hubert Toronto Island

11:45 a.m. - 12:55 a.m.MDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

C$ 674Multiple Airlines

Thu, 29 Oct - Fri, 6 Nov

6:00 a.m. - 11:40 a.m.YYT St John's-ORD Chicago O'Hare Intl

8h 10m2 stops Ottawa Toronto Island

6:20 p.m. - 1:30 p.m.ORD Chicago O'Hare Intl-YYT St John's

16h 40m1 stop Toronto Island

C$ 706Porter Airlines

Thu, 29 Oct - Fri, 6 Nov

6:00 a.m. - 11:40 a.m.YYT St John's-ORD Chicago O'Hare Intl

8h 10m2 stops Ottawa Toronto Island

12:20 p.m. - 12:57 a.m.ORD Chicago O'Hare Intl-YYT St John's

10h 07m2 stops Toronto Island Ottawa

C$ 768Porter Airlines

Thu, 1 Oct - Wed, 7 Oct

5:45 a.m. - 10:12 a.m.YYT St John's-ORD Chicago O'Hare Intl

6h 57m1 stop Montreal Pierre Elliott Trudeau Intl

3:45 p.m. - 1:46 a.m.ORD Chicago O'Hare Intl-YYT St John's

7h 31m1 stop Toronto Pearson Intl

C$ 789Air Canada

Thu, 29 Oct - Fri, 6 Nov

6:00 a.m. - 11:40 a.m.YYT St John's-ORD Chicago O'Hare Intl

8h 10m2 stops Ottawa Toronto Island

6:20 p.m. - 2:30 p.m.ORD Chicago O'Hare Intl-YYT St John's

17h 40m3 stops Toronto Island Montreal St Hubert Halifax Intl

C$ 804Porter Airlines

Recent last minute flight deals from Newfoundland and Labrador to Chicago

Fri, 18 Sep - Sun, 20 Sep

6:05 a.m. - 2:35 p.m.YYT St John's-MDW Chicago Midway

11h 00m2 stops Ottawa Toronto Island

3:20 p.m. - 12:55 a.m.MDW Chicago Midway-YYT St John's

7h 05m2 stops Toronto Island Ottawa

C$ 967Porter Airlines

Fri, 18 Sep - Sun, 20 Sep

6:05 a.m. - 2:35 p.m.YYT St John's-MDW Chicago Midway

11h 00m2 stops Ottawa Toronto Island

11:45 a.m. - 12:55 a.m.MDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

C$ 972Porter Airlines

Fri, 18 Sep - Sun, 20 Sep

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

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$ 1,050Air Canada

Fri, 18 Sep - Sun, 20 Sep

8:40 p.m. - 10:15 a.m.YYT St John's-ORD Chicago O'Hare Intl

16h 05m2 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl

2:00 p.m. - 12:33 a.m.ORD Chicago O'Hare Intl-YYT St John's

8h 03m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl

C$ 1,104Air Canada

Fri, 18 Sep - Sun, 20 Sep

5:30 a.m. - 2:52 p.m.YYT St John's-ORD Chicago O'Hare Intl

11h 52m1 stop Montreal Pierre Elliott Trudeau Intl

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$ 1,106Air Canada

Fri, 18 Sep - Sun, 20 Sep

8:40 p.m. - 10:15 a.m.YYT St John's-ORD Chicago O'Hare Intl

16h 05m2 stops Halifax Intl Montreal Pierre Elliott Trudeau Intl

2:00 p.m. - 12:33 a.m.ORD Chicago O'Hare Intl-YYT St John's

8h 03m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl

C$ 1,107Air Canada

Fri, 18 Sep - Sun, 20 Sep

6:05 a.m. - 11:00 a.m.YYT St John's-MDW Chicago Midway

31h 25m2 stops Ottawa Toronto Island

11:45 a.m. - 12:55 a.m.MDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

C$ 1,116Porter Airlines

Fri, 18 Sep - Sun, 20 Sep

6:00 a.m. - 2:35 p.m.YYT St John's-MDW Chicago Midway

11h 05m2 stops Montreal St Hubert Toronto Island

11:45 a.m. - 12:55 a.m.MDW Chicago Midway-YYT St John's

10h 40m2 stops Toronto Island Ottawa

C$ 1,163Porter Airlines

Fri, 18 Sep - Sun, 20 Sep

6:05 a.m. - 2:35 p.m.YYT St John's-MDW Chicago Midway

11h 00m2 stops Ottawa Toronto Island

11:45 a.m. - 10:55 p.m.MDW Chicago Midway-YYT St John's

32h 40m2 stops Toronto Island Montreal St Hubert

C$ 1,317Porter Airlines

Fri, 18 Sep - Sun, 20 Sep

5:40 p.m. - 12:00 p.m.YYT St John's-ORD Chicago O'Hare Intl

20h 50m1 stop Toronto Pearson Intl

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$ 1,342Air Canada

Useful Info

Cheapest flight	C$ 356

Flight from St. John's to Chicago

How does KAYAK find such low prices on flights from Newfoundland and Labrador to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Newfoundland and Labrador to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Newfoundland and Labrador to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Newfoundland and Labrador is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Newfoundland and Labrador to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Newfoundland and Labrador with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Newfoundland and Labrador to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Newfoundland and Labrador up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.