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Cheap flights from St. John's to Chicago from C$ 342

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 29/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYT — CHI
20 May — 27 May1
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 15 May 2025.

Round-trip from

C$ 689

One-way from

C$ 342
Air Canada
  • Air Canada
  • 28/6-2/7
  • 3 total stops
  • 21h 38m total
  • St. John's to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/6
  • 3 total stops
  • 20h 15m 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 15 May 2025.

Sun 5/102:00 p.m.YYT - ORD
1 stop8h 41mUnited Airlines
Thu 9/104:00 p.m.ORD - YYT
2 stops18h 34mUnited Airlines
Deal found 14/5C$ 620
Sat 28/67:15 p.m.YYT - ORD
2 stops16h 23mAir Canada
Wed 2/73:35 p.m.ORD - YYT
1 stop6h 28mAir Canada
Deal found 14/5C$ 664
Fri 13/65:00 a.m.YYT - ORD
1 stop7h 29mMultiple Airlines
Fri 20/68:25 p.m.ORD - YYT
2 stops15h 08mMultiple Airlines
Deal found 14/5C$ 668
Sat 28/63:00 p.m.YYT - MDW
2 stops20h 15mPorter Airlines
Wed 2/79:40 a.m.MDW - YYT
2 stops12h 18mPorter Airlines
Deal found 14/5C$ 956

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 15 May 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

Sun 5/10

2:00 p.m.-8:11 p.m.

1 stop8h 41m

Chicago O'Hare Intl

Thu 9/10

4:00 p.m.-1:04 p.m.

2 stops18h 34m

C$ 620

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 28/6

7:15 p.m.-9:08 a.m.

2 stops16h 23m

Chicago O'Hare Intl

Wed 2/7

3:35 p.m.-12:33 a.m.

1 stop6h 28m

C$ 664

St. John'sChicago

YYT - ORD

YYTORD

St John's

Fri 13/6

5:00 a.m.-9:59 a.m.

1 stop7h 29m

Chicago O'Hare Intl

Fri 20/6

8:25 p.m.-2:03 p.m.

2 stops15h 08m

C$ 668

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sat 28/6

3:00 p.m.-8:45 a.m.

2 stops20h 15m

Chicago Midway

Wed 2/7

9:40 a.m.-12:28 a.m.

2 stops12h 18m

C$ 956

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Sun 29/6

3:00 p.m.-8:45 a.m.

3 stops20h 15m

C$ 342

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 15/6

3:05 p.m.-9:19 p.m.

1 stop32h 44m

C$ 379

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 29/6

5:50 a.m.-3:16 p.m.

2 stops11h 56m

C$ 386

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/5

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 15 May 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 15 May 2025.
Porter Airlines
8.0
Very good
286 reviews
Check prices

Crew

8.7

Comfort

8.1

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
286 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Crew

8.7

Comfort

8.1

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,731 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Crew

8.7

Comfort

8.1

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,338 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Crew

8.7

Comfort

8.1

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 689, 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. Check Cheapflights for deals on Porter Airlines for as low as C$ 1,114.

  • 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$ 353). 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 15 May 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 641AverageC$ 767FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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