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Cheap flights from St. John's to Chicago from C$ 348

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
7 Jul — 14 Jul1
1 adult

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 2 July 2025.

Round-trip from

C$ 536

One-way from

C$ 348
Air Canada
  • Air Canada
  • 30/9-30/9
  • 2 total stops
  • 13h 05m total
  • St. John's to Chicago
Search Deals
Air Canada
  • Air Canada
  • 11/11
  • 1 total stop
  • 17h 33m total
  • St. John's to Chicago
Search Deals

Find flight deals from St. John's to Chicago

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 2 July 2025.

Tue 30/95:50 a.m.YYT - ORD
1 stop6h 31mAir Canada
Tue 30/93:35 p.m.ORD - YYT
1 stop6h 34mAir Canada
Deal found 2/7C$ 536
Tue 30/95:50 a.m.YYT - ORD
1 stop6h 31mMultiple Airlines
Tue 30/91:55 p.m.ORD - YYT
2 stops8h 14mMultiple Airlines
Deal found 2/7C$ 641
Tue 30/95:50 a.m.YYT - ORD
2 stops10h 53mUnited Airlines
Tue 30/96:00 p.m.ORD - YYT
2 stops16h 34mUnited Airlines
Deal found 2/7C$ 642
Wed 5/114:15 p.m.YYT - MDW
2 stops20h 35mPorter Airlines
Mon 10/1111:15 a.m.MDW - YYT
2 stops9h 55mPorter Airlines
Deal found 2/7C$ 805

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 2 July 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 30/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

Chicago O'Hare Intl

Tue 30/9

3:35 p.m.-12:39 a.m.

1 stop6h 34m

C$ 536

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 30/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

Chicago O'Hare Intl

Tue 30/9

1:55 p.m.-12:39 a.m.

2 stops8h 14m

C$ 641

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 30/9

5:50 a.m.-2:13 p.m.

2 stops10h 53m

Chicago O'Hare Intl

Tue 30/9

6:00 p.m.-1:04 p.m.

2 stops16h 34m

C$ 642

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 5/11

4:15 p.m.-10:20 a.m.

2 stops20h 35m

Chicago Midway

Mon 10/11

11:15 a.m.-11:40 p.m.

2 stops9h 55m

C$ 805

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 11/11

6:10 p.m.-9:13 a.m.

1 stop17h 33m

C$ 348

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 11/11

5:10 a.m.-2:11 p.m.

2 stops11h 31m

C$ 367

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 16/8

1:10 p.m.-11:59 p.m.

2 stops13h 19m

C$ 459

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 11/11

6:25 a.m.-10:20 a.m.

2 stops30h 25m

C$ 530

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 16/8

3:00 p.m.-3:06 p.m.

3 stops26h 36m

C$ 736

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

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 is the cheapest time of day to fly from YYT to CHI?

Find hourly flight availability from St. John's to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 2 July 2025.

It’s optimal to fly from St. John's to Chicago in the morning. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the afternoon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 2 July 2025.
Get a feel of what it's like to fly with Porter Airlines,United Airlines, andAir Canada from St. John's to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
298 reviews
Check prices

Comfort

8.1

Boarding

8.2

Food

7.7

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Comfort

8.1

Boarding

8.2

Food

7.7

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,861 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Comfort

8.1

Boarding

8.2

Food

7.7

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,671 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Comfort

8.1

Boarding

8.2

Food

7.7

Overall

8.0

Entertainment

7.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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.

  • What are the cheapest airlines flying from St. John's to Chicago round-trip?

    Currently priced at C$ 536, Air Canada will fly you from St. John's to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Porter Airlines - these airlines can fly you to your destination from C$ 642 and C$ 805, respectively.

  • What are the cheapest airlines to fly from St. John's to Chicago one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as C$ 348. Users have also found prices from C$ 367 and C$ 530 on United Airlines and Porter Airlines, respectively.

  • 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.

  • What is the cheapest month to book a flight from St. John's to Chicago?

    Currently, January is the cheapest month in which you can book a flight from St. John's to Chicago (average of C$ 261). Flying from St. John's to Chicago in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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 2 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 625AverageC$ 787FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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How does Cheapflights help users find flights 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.

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