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Cheap flights from St. John's to Chicago from C$ 375

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 30/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
1 May — 8 May1
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 1 April 2026.

Sat 5/126:20 a.m.
YYT
-
ORD
2 stops8h 00m
Porter Airlines
Tue 8/1211:00 a.m.
ORD
-
YYT
2 stops9h 45m
Porter Airlines
Deal found 30/3C$ 617
Sat 5/125:05 a.m.
YYT
-
ORD
1 stop8h 35m
Air Canada
Tue 8/123:55 p.m.
ORD
-
YYT
1 stop6h 31m
Air Canada
Deal found 30/3C$ 645
Tue 5/52:00 p.m.
YYT
-
ORD
1 stop8h 38m
Air Canada
Wed 6/58:45 a.m.
ORD
-
YYT
2 stops8h 28m
Air Canada
Deal found 30/3C$ 671
Tue 11/86:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Wed 12/83:20 p.m.
MDW
-
YYT
2 stops7h 05m
Porter Airlines
Deal found 31/3C$ 673
Sat 18/46:20 a.m.
YYT
-
MDW
2 stops8h 20m
Porter Airlines
Wed 22/411:00 a.m.
MDW
-
YYT
2 stops11h 31m
Porter Airlines
Deal found 29/3C$ 674
Sat 16/55:35 a.m.
YYT
-
ORD
1 stop7h 13m
Air Canada
Sat 23/53:50 p.m.
ORD
-
YYT
1 stop7h 28m
Air Canada
Deal found 1/4C$ 678
Sat 16/53:00 p.m.
YYT
-
ORD
2 stops21h 46m
WestJet
Sat 23/511:09 a.m.
ORD
-
YYT
2 stops9h 16m
WestJet
Deal found 1/4C$ 857
Sat 16/53:00 p.m.
YYT
-
MDW
2 stops20h 13m
WestJet
Sat 23/59:22 a.m.
MDW
-
YYT
2 stops35h 03m
WestJet
Deal found 1/4C$ 960
Sat 16/56:05 a.m.
YYT
-
MDW
3 stops14h 58m
Multiple Airlines
Sat 23/510:30 a.m.
MDW
-
YYT
2 stops11h 55m
Multiple Airlines
Deal found 1/4C$ 1,425

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 1 April 2026.

Round-trip from

C$ 671

One-way from

C$ 375
Air Canada
  • Air Canada
  • 5/5-6/5
  • 3 total stops
  • 17h 06m total
  • St. John's to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 30/6
  • 2 total stops
  • 11h 00m 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 1 April 2026.
Use the filters below to find and compare flights from St. John's to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 5/5

2:00 p.m.-8:08 p.m.

1 stop8h 38m

Chicago O'Hare Intl

Wed 6/5

8:45 a.m.-7:43 p.m.

2 stops8h 28m

C$ 671

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 11/8

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

2 stops11h 00m

Chicago Midway

Wed 12/8

10:25 a.m.-12:55 a.m.

2 stops12h 00m

C$ 673

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 18/4

6:20 a.m.-12:10 p.m.

2 stops8h 20m

Chicago Midway

Wed 22/4

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

2 stops11h 31m

C$ 674

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 16/5

6:05 a.m.-6:33 p.m.

3 stops14h 58m

Chicago Midway

Sat 23/5

10:30 a.m.-12:55 a.m.

2 stops11h 55m

C$ 1,425
Cheapest one-way
Quickest one-way

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 30/6

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

2 stops11h 00m

C$ 375

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 8/8

8:00 p.m.-9:00 a.m.

1 stop15h 30m

C$ 415

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 11/5

5:35 a.m.-2:19 p.m.

2 stops11h 14m

C$ 454

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 30/6

3:00 p.m.-7:32 p.m.

2 stops31h 02m

C$ 456

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 11/5

6:05 a.m.-11:59 p.m.

3 stops20h 24m

C$ 481

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 8/8

6:00 a.m.-9:40 a.m.

2 stops30h 10m

C$ 486

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/3

Showing 1-10 of 12 resultsSorted by cheapest first
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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.

Montreal (YUL) – chosen by Cheapflights users on 50% 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$ 688.

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: 6h 50m.

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 22m.

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 0 airlines. 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 8h 38m. Fly via Air Canada or Porter Airlines 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

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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

Fly with Cheapflights

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

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

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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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