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St. John's

$528+ Cheap flights from Chicago (CHI) to St. John's (YYT)

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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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Find flight deals from Chicago to St. John's

Cheapest flights from Chicago to St. John's
Explore the most affordable flight options available from Chicago to St. John's. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2025.

This FlightHub deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:00 amMDW - YYT
2 stops9h 45mPorter Airlines
Mon 12/156:00 amYYT - MDW
2 stops11h 50mPorter Airlines
Deal found 11/19$573
This Air Canada deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/127:05 amORD - YYT
1 stop7h 46mAir Canada
Mon 12/155:05 amYYT - ORD
1 stop8h 43mAir Canada
Deal found 11/19$592
This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:48 amORD - YYT
2 stops15h 43mMultiple Airlines
Wed 11/266:20 amYYT - ORD
2 stops19h 16mMultiple Airlines
Deal found 11/20$1,118
This United Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/222:39 pmORD - YYT
2 stops19h 29mUnited Airlines
Sat 11/295:05 amYYT - ORD
1 stop8h 43mUnited Airlines
Deal found 11/19$1,185
This Gotogate deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2411:00 amMDW - YYT
2 stops9h 45mPorter Airlines
Wed 11/266:00 amYYT - MDW
2 stops30h 35mPorter Airlines
Deal found 11/20$1,187
This Air Canada deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:05 amORD - YYT
1 stop7h 46mAir Canada
Sat 11/296:10 pmYYT - ORD
1 stop16h 15mAir Canada
Deal found 11/20$1,301
This Mytrip deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:21 pmORD - YYT
3 stops27h 10mMultiple Airlines
Sat 11/296:20 amYYT - ORD
2 stops15h 30mMultiple Airlines
Deal found 11/19$1,308
This Air Canada deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/243:35 pmORD - YYT
1 stop6h 51mAir Canada
Wed 11/265:05 amYYT - ORD
1 stop8h 43mAir Canada
Deal found 11/20$1,333
This FlightHub deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2212:45 pmMDW - YYT
2 stops9h 46mPorter Airlines
Sat 11/296:20 amYYT - MDW
2 stops8h 00mPorter Airlines
Deal found 11/20$1,337
This Mytrip deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/229:41 amMDW - YYT
3 stops35h 04mMultiple Airlines
Sat 11/294:15 pmYYT - MDW
3 stops20h 20mMultiple Airlines
Deal found 11/19$1,857

Cheap flight deals from Chicago to St. John's

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to St. John's (YYT). 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 November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$528
(Air Canada)
Provider with most accurate pricing for Chicago (CHI)-St John's flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-St John's flights.
Search Deals
From Chicago (CHI) to St John's
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to St. John's 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 2,558,603 searches. Data last updated November 21, 2025.
Use the filters below to find and compare flights from Chicago to St. John's that are best for you.

Fly from

Chicago

Fly to

St. John's

Route

Depart

Return

Price

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 1/3

3:55 pm-1:33 am

1 stop7h 08m

St John's

Sat 1/10

5:05 am-11:06 am

1 stop8h 31m

$528

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 1/22

7:15 am-8:15 pm

2 stops10h 30m

St John's

Mon 1/26

5:05 am-11:06 am

1 stop8h 31m

$561

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 12/12

11:00 am-11:15 pm

2 stops9h 45m

St John's

Mon 12/15

6:00 am-3:20 pm

2 stops11h 50m

$573

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 12/12

7:05 am-5:21 pm

1 stop7h 46m

St John's

Mon 12/15

5:05 am-11:18 am

1 stop8h 43m

$592

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 1/3

3:55 pm-1:33 am

1 stop7h 08m

St John's

Sat 1/10

5:05 am-9:29 pm

2 stops18h 54m

$608

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 1/3

11:05 am-1:06 am

2 stops11h 31m

St John's

Sat 1/10

6:20 am-11:50 am

2 stops8h 00m

$675

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 1/3

11:00 am-11:15 pm

3 stops9h 45m

St John's

Sat 1/10

6:20 am-11:50 am

2 stops8h 00m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Compare providers for flights from Chicago to St. John's

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to St. John's in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-St. John's flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-St. John's flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-St. John's flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-St. John's flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-St. John's flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to St. John's

Have a flexible travel schedule? Discover the best time to fly to St. John's from Chicago 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 Chicago to St. John's

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

Find hourly flight availability from Chicago to St. John's. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to St. John's in the evening. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing St. John's

Get insights into the airlines that provide service to St. John's. 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 St. John's. Reviews last updated November 21, 2025.
Read reviews from past customers who have flown United Airlines and Air Canada from Chicago to St. John's. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,028 reviews

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,028 reviews
United Airlines
7.4
Good
9,028 reviews

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,463 reviews
United Airlines
7.4
Good
9,028 reviews

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from Chicago to St. John's. 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 into for flights to St. John's from Chicago?

    For a flight from Chicago to St. John's, you will be flying into St John's. St John's (YYT) is just 4.2 mi from the center of the city. St John's is the only St. John's airport and it handles 0 inbound flights from Chicago per day. 2 airlines have flights to St John's from Chicago on a regular basis.

  • How long is the flight from Chicago to St. John's?

    Departing from Chicago to St. John's will take you 7h 08m. The distance from Chicago to St. John's is about 1750 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, United Airlines ($252), and Air Canada ($498) offers the cheapest pricing from Chicago to St. John's.

  • Can I find deals for flights from Chicago to St. John's that include hotel bookings?

    Yes. In addition to deals on Chicago to St. John's flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to St. John's?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to St. John's.

  • Can I find deals for business class flights from Chicago to St. John's?

    Yes. Cheapflights offers flight deals from Chicago to St. John's 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

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Alternative routes for Chicago to St. John's

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to St. John's flights
Midway to St. John's flights
St. Louis to St. John's flights
O'Hare Intl to Deer Lake flights

Top 2 airlines flying from Chicago to St. John's

Discover the top 2 airlines that operate flights from Chicago to St. John's. 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 2,558,603 searches. Data last updated November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$252Average$602FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$498Average$669FlexibilityNo cancel feeOn-time67%

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