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Cheap flights from St. John's to Chicago from C$ 340

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 31/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
5 Jun — 12 Jun1
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 6 May 2026.

Mon 31/85:35 a.m.
YYT
-
ORD
2 stops10h 05m
Air Canada
Thu 3/98:45 a.m.
ORD
-
YYT
2 stops12h 13m
Air Canada
Deal found 5/5C$ 749
Tue 26/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Tue 2/610:15 a.m.
MDW
-
YYT
2 stops12h 11m
Porter Airlines
Deal found 2/5C$ 808
Tue 26/55:40 p.m.
YYT
-
ORD
1 stop6h 55m
United Airlines
Tue 2/69:34 p.m.
ORD
-
YYT
2 stops12h 57m
United Airlines
Deal found 2/5C$ 821
Tue 12/56:05 a.m.
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Tue 19/510:30 a.m.
MDW
-
YYT
2 stops11h 55m
Porter Airlines
Deal found 3/5C$ 896
Tue 15/93:00 p.m.
YYT
-
MDW
2 stops24h 41m
Delta
Sat 19/95:59 p.m.
MDW
-
YYT
2 stops26h 26m
Delta
Deal found 5/5C$ 1,141

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 6 May 2026.

Round-trip from

C$ 749

One-way from

C$ 340
Air Canada
  • Air Canada
  • 31/8-3/9
  • 4 total stops
  • 22h 18m total
  • St. John's to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 31/5
  • 2 total stops
  • 18h 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 6 May 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

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

8:45 a.m.-11:28 p.m.

2 stops12h 13m

C$ 749

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

Tue 2/6

10:15 a.m.-12:56 a.m.

2 stops12h 11m

C$ 808
Quickest round-trip

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 26/5

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

1 stop6h 55m

Chicago O'Hare Intl

Tue 2/6

9:34 p.m.-1:01 p.m.

2 stops12h 57m

C$ 821

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-1:11 p.m.

2 stops24h 41m

Chicago Midway

Sat 19/9

5:59 p.m.-10:55 p.m.

2 stops26h 26m

C$ 1,141
Cheapest one-way

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 2/6

6:05 a.m.-9:35 a.m.

2 stops30h 00m

C$ 340

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 31/5

6:05 p.m.-9:35 a.m.

2 stops18h 00m

C$ 340

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Mon 1/6

6:05 a.m.-9:35 a.m.

2 stops30h 00m

C$ 345

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 2/6

3:00 p.m.-12:24 p.m.

2 stops47h 54m

C$ 395

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 1/6

6:05 a.m.-7:55 a.m.

3 stops28h 20m

C$ 396

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 20/6

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

2 stops30h 10m

C$ 407

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 19 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$ 673.

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 10h 05m. Fly via Air Canada, Porter Airlines, or Delta 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.
Deer Lake to O'Hare Intl flights
St. John's 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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