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Cheap flights from St. John's to Chicago from C$ 344

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 13/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
26 Feb — 5 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from St. John's to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from St. John's to Chicago
Explore the most affordable flight options available from St. John's to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 January 2026.

Tue 21/46:20 a.m.
YYT
-
MDW
2 stops11h 30m
Porter Airlines
Sun 26/411:00 a.m.
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Deal found 25/1C$ 571
Tue 21/46:20 a.m.
YYT
-
MDW
2 stops30h 15m
Multiple Airlines
Mon 27/411:00 a.m.
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 25/1C$ 579
Tue 21/46:20 a.m.
YYT
-
MDW
2 stops30h 15m
Multiple Airlines
Sun 26/411:00 a.m.
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 25/1C$ 583
Wed 22/45:40 p.m.
YYT
-
MDW
1 stop18h 55m
Multiple Airlines
Tue 28/44:15 p.m.
MDW
-
YYT
1 stop28h 10m
Multiple Airlines
Deal found 25/1C$ 590
Wed 22/45:40 p.m.
YYT
-
MDW
1 stop18h 55m
Multiple Airlines
Sun 26/411:00 a.m.
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 25/1C$ 593
Thu 23/45:25 a.m.
YYT
-
ORD
1 stop7h 58m
Air Canada
Mon 27/44:15 p.m.
ORD
-
YYT
1 stop6h 53m
Air Canada
Deal found 26/1C$ 605
Fri 24/46:35 a.m.
YYT
-
ORD
1 stop8h 55m
Air Canada
Tue 28/44:15 p.m.
ORD
-
YYT
1 stop6h 53m
Air Canada
Deal found 26/1C$ 612
Thu 23/45:25 a.m.
YYT
-
ORD
2 stops10h 05m
Air Canada
Sun 26/44:15 p.m.
ORD
-
YYT
1 stop6h 53m
Air Canada
Deal found 26/1C$ 616
Wed 22/45:40 p.m.
YYT
-
MDW
1 stop18h 55m
Porter Airlines
Sun 26/411:00 a.m.
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Deal found 25/1C$ 616
Wed 22/46:00 a.m.
YYT
-
MDW
2 stops11h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YYT
2 stops9h 35m
Porter Airlines
Deal found 25/1C$ 620
Thu 23/44:15 p.m.
YYT
-
MDW
2 stops20h 20m
Multiple Airlines
Sun 26/411:00 a.m.
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 26/1C$ 623
Fri 24/46:20 a.m.
YYT
-
MDW
2 stops11h 30m
Multiple Airlines
Mon 27/411:00 a.m.
MDW
-
YYT
1 stop9h 25m
Multiple Airlines
Deal found 25/1C$ 627

Find flight deals from St. John's to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from St. John's (YYT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 27 January 2026.

Round-trip from

C$ 571

One-way from

C$ 344
Porter Airlines
  • Porter Airlines
  • 21/4-26/4
  • 4 total stops
  • 23h 01m total
  • St. John's to Chicago
Search Deals
Air Canada
  • Air Canada
  • 13/3
  • 1 total stop
  • 8h 56m total
  • St. John's to Chicago
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from St. John's 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, Cheapflights users made 629,999 searches. Data last updated 27 January 2026.
Use the filters below to find and compare flights from St. John's to Chicago that are best for you.

Fly from

St. John's

Fly to

Chicago

Route

Depart

Return

Price

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 21/4

6:20 a.m.-3:20 p.m.

2 stops11h 30m

Chicago Midway

Sun 26/4

11:00 a.m.-1:01 a.m.

2 stops11h 31m

C$ 571

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 21/4

6:20 a.m.-3:20 p.m.

2 stops11h 30m

Chicago Midway

Mon 27/4

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

2 stops9h 35m

C$ 571

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 21/4

6:20 a.m.-3:20 p.m.

2 stops11h 30m

Chicago Midway

Tue 28/4

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

2 stops9h 35m

C$ 571

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 21/4

6:20 a.m.-10:05 a.m.

2 stops30h 15m

Chicago Midway

Tue 28/4

11:00 a.m.-10:55 p.m.

1 stop9h 25m

C$ 579

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 21/4

6:20 a.m.-10:05 a.m.

2 stops30h 15m

Chicago Midway

Sun 26/4

11:00 a.m.-10:55 p.m.

1 stop9h 25m

C$ 583

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 22/4

5:40 p.m.-3:20 p.m.

1 stop24h 10m

Chicago Midway

Mon 27/4

11:00 a.m.-10:55 p.m.

1 stop9h 25m

C$ 590

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 22/4

5:40 p.m.-10:05 a.m.

1 stop18h 55m

Chicago Midway

Tue 28/4

4:15 p.m.-10:55 p.m.

1 stop28h 10m

C$ 590

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 23/4

5:25 a.m.-10:53 a.m.

1 stop7h 58m

Chicago O'Hare Intl

Mon 27/4

4:15 p.m.-1:38 a.m.

1 stop6h 53m

C$ 605

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 23/4

5:25 a.m.-10:53 a.m.

1 stop7h 58m

Chicago O'Hare Intl

Tue 28/4

7:55 a.m.-5:03 p.m.

1 stop6h 38m

C$ 605

St. John'sChicago

YYT - ORD

YYTORD

St John's

Fri 24/4

6:35 a.m.-1:00 p.m.

1 stop8h 55m

Chicago O'Hare Intl

Tue 28/4

4:15 p.m.-1:38 a.m.

1 stop6h 53m

C$ 612

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Showing 1-10 of 21 results
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Best time to book a flight from St. John's to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St. John's with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from St. John's to Chicago

What’s the top layover airport for flights from St. John's to Chicago?

Share of one-stop round-trip flights from St. John's to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 71% of one-stop itineraries from St. John's to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from St. John's to Chicago?

Average round-trip fare for 1-stop flights from St. John's to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 694.

What’s the fastest layover option from St. John's to Chicago?

Shortest average travel time for 1-stop one-way flights from St. John's to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 7h 11m.

Which airport typically offers the quickest layover for flights from St. John's to Chicago?

Average layover duration for 1-stop one-way flights from St. John's to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 41m.

Related info for your journey

Find useful and relevant information for your journey from St. John's to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from St. John's to Chicago?

    Most people fly from St John's (YYT) if they book a flight from St. John's to Chicago. On average, St John's has 0 outbound flights to Chicago per day from 1 airline. St John's is conveniently located just 6.7 km from St. John's’s city centre.

  • How long is the flight from St. John's to Chicago?

    There are many flights that can get you from St. John's to Chicago in 7h 58m. Fly via Porter Airlines or Air Canada to get the fastest option. Airlines will cover a distance of 2816 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • Can I find deals for flights from St. John's to Chicago that include hotel bookings?

    Yes. In addition to deals on St. John's to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from St. John's to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. John's to Chicago.

  • Can I find deals for business class flights from St. John's to Chicago?

    Yes. Cheapflights offers flight deals from St. John's to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for St. John's to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
St. John's to O'Hare Intl flights
Deer Lake to O'Hare Intl flights

Top airline flying from St. John's to Chicago

Discover the top airline that operate flights from St. John's to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 27 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 668AverageC$ 706FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from St. John's to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from St. John's today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from St. John's to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from St. John's to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from St. John's to Chicago with no change fees?

Certainly. Search results for flights to Chicago from St. John's shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from St. John's to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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