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Cheap flights from St. John's to Chicago from C$ 581

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
15 Nov — 22 Nov1
1 adult
1 adult, Economy

Cheap 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 16 October 2025.

Round-trip from

C$ 581
28/10-19/11
  • 28/10-19/11
  • 6 total stops
  • 52h 18m total
  • St. John's to Chicago
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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 16 October 2025.

Tue 28/106:20 a.m.YYT - ORD
3 stops21h 13mMultiple Airlines
Wed 19/113:26 p.m.ORD - YYT
3 stops31h 05mMultiple Airlines
Deal found 14/10C$ 581
Thu 13/116:20 a.m.YYT - MDW
2 stops11h 30mPorter Airlines
Thu 20/1111:00 a.m.MDW - YYT
2 stops11h 31mPorter Airlines
Deal found 15/10C$ 657
Wed 12/116:20 a.m.YYT - ORD
2 stops19h 16mMultiple Airlines
Wed 19/113:26 p.m.ORD - YYT
3 stops31h 05mMultiple Airlines
Deal found 14/10C$ 667
Thu 13/119:45 a.m.YYT - ORD
1 stop30h 20mMultiple Airlines
Thu 20/116:48 a.m.ORD - YYT
2 stops15h 43mMultiple Airlines
Deal found 15/10C$ 684
Tue 28/106:20 a.m.YYT - ORD
3 stops21h 13mMultiple Airlines
Fri 31/107:43 p.m.ORD - YYT
3 stops26h 48mMultiple Airlines
Deal found 14/10C$ 709
Thu 13/116:35 a.m.YYT - ORD
1 stop8h 56mAir Canada
Thu 20/117:05 a.m.ORD - YYT
1 stop7h 46mAir Canada
Deal found 16/10C$ 712
Wed 12/111:30 p.m.YYT - ORD
1 stop8h 30mAir Canada
Wed 19/113:55 p.m.ORD - YYT
1 stop7h 08mAir Canada
Deal found 14/10C$ 720
Thu 13/116:20 a.m.YYT - MDW
2 stops20h 05mMultiple Airlines
Thu 20/1111:00 a.m.MDW - YYT
1 stop27h 15mMultiple Airlines
Deal found 15/10C$ 734
Wed 12/115:40 p.m.YYT - MDW
1 stop18h 55mPorter Airlines
Wed 19/1111:00 a.m.MDW - YYT
2 stops11h 31mPorter Airlines
Deal found 14/10C$ 750
Tue 28/106:20 a.m.YYT - MDW
2 stops11h 30mPorter Airlines
Wed 19/1111:00 a.m.MDW - YYT
2 stops9h 45mPorter Airlines
Deal found 14/10C$ 771
Tue 28/105:05 a.m.YYT - ORD
1 stop8h 43mAir Canada
Wed 19/113:55 p.m.ORD - YYT
1 stop7h 08mAir Canada
Deal found 14/10C$ 785
Wed 12/115:00 a.m.YYT - ORD
2 stops12h 10mUnited Airlines
Wed 19/1110:00 a.m.ORD - YYT
2 stops12h 26mUnited Airlines
Deal found 14/10C$ 792

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 16 October 2025.
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 - ORD

YYTORD

St John's

Tue 28/10

6:20 a.m.-9:33 p.m.

2 stops17h 43m

Chicago O'Hare Intl

Wed 19/11

3:26 p.m.-1:01 a.m.

3 stops31h 05m

C$ 601

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 13/11

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

2 stops11h 30m

Chicago Midway

Thu 20/11

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

2 stops11h 31m

C$ 657

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 12/11

6:20 a.m.-11:06 p.m.

2 stops19h 16m

Chicago O'Hare Intl

Wed 19/11

3:26 p.m.-1:01 a.m.

3 stops31h 05m

C$ 667

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 13/11

9:45 a.m.-1:35 p.m.

1 stop30h 20m

Chicago O'Hare Intl

Thu 20/11

6:48 a.m.-1:01 a.m.

2 stops15h 43m

C$ 684

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 28/10

6:20 a.m.-1:03 a.m.

3 stops21h 13m

Chicago O'Hare Intl

Fri 31/10

7:43 p.m.-1:01 a.m.

3 stops26h 48m

C$ 709

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 13/11

6:35 a.m.-1:01 p.m.

1 stop8h 56m

Chicago O'Hare Intl

Thu 20/11

7:05 a.m.-5:21 p.m.

1 stop7h 46m

C$ 712

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 13/11

6:20 a.m.-11:55 p.m.

2 stops20h 05m

Chicago Midway

Thu 20/11

11:00 a.m.-4:45 p.m.

1 stop27h 15m

C$ 734

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 12/11

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

1 stop18h 55m

Chicago Midway

Wed 19/11

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

2 stops11h 31m

C$ 750

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 28/10

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

2 stops11h 30m

Chicago Midway

Wed 19/11

11:00 a.m.-11:15 p.m.

2 stops9h 45m

C$ 771

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 12/11

5:00 a.m.-10:05 a.m.

1 stop7h 35m

Chicago O'Hare Intl

Wed 19/11

9:05 p.m.-5:21 p.m.

2 stops17h 46m

C$ 785

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/10

Showing 1-10 of 15 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 75% 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$ 712.

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 17m.

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 47m.

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 11h 30m. Fly via Porter Airlines to get the fastest option. Airlines will cover a distance of 2813 km.

  • 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

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 16 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 715AverageC$ 811FlexibilityNo cancel feeOn-time67%
Search Air Canada 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?

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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