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St. John's

$309+ Cheap flights from Chicago (CHI) to St. John's (YYT)

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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
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Cheap 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 May 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1310:15 am
MDW
-
YYT
1 stop9h 25m
Porter Airlines
Sun 6/217:00 pm
YYT
-
MDW
1 stop17h 10m
Porter Airlines
Deal found 5/10$539
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1910:25 am
MDW
-
YYT
1 stop11h 40m
Porter Airlines
Sat 6/276:00 am
YYT
-
MDW
2 stops30h 10m
Porter Airlines
Deal found 5/8$551
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:15 am
MDW
-
YYT
2 stops12h 11m
Porter Airlines
Thu 6/117:00 pm
YYT
-
MDW
1 stop17h 05m
Porter Airlines
Deal found 5/9$558
This Gotogate deal was found by Cheapflights users on 5/7. 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.
Tue 9/13:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Wed 9/161:45 pm
YYT
-
ORD
2 stops10h 20m
Porter Airlines
Deal found 5/7$571
This Gotogate deal was found by Cheapflights users on 5/8. 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.
Thu 9/243:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sat 9/266:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 5/8$576
This Booking.com deal was found by Cheapflights users on 5/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sun 10/46:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 5/10$577
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am
ORD
-
YYT
1 stop13h 25m
Multiple Airlines
Sat 9/263:00 pm
YYT
-
ORD
1 stop26h 05m
Multiple Airlines
Deal found 5/8$583
This Justfly.com deal was found by Cheapflights users on 5/11. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2310:25 am
MDW
-
YYT
2 stops10h 00m
Porter Airlines
Sun 6/286:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 5/11$597
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:20 pm
ORD
-
YYT
2 stops21h 15m
Multiple Airlines
Sun 9/203:00 pm
YYT
-
ORD
1 stop22h 30m
Multiple Airlines
Deal found 5/11$598
This Gotogate deal was found by Cheapflights users on 5/8. 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 7/2010:25 am
MDW
-
YYT
2 stops12h 00m
Porter Airlines
Wed 7/296:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 5/8$599
This Mytrip deal was found by Cheapflights users on 5/11. 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.
Thu 9/107:00 am
ORD
-
YYT
2 stops13h 25m
Multiple Airlines
Sun 9/136:00 am
YYT
-
ORD
2 stops18h 05m
Multiple Airlines
Deal found 5/11$600
This FlightHub deal was found by Cheapflights users on 5/12. 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.
Thu 9/33:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sat 9/126:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 5/12$603

Find 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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$539
(Kiwi.com)

One-way from

$309
(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
One-way flight 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 May 12, 2026.
Use the filters below to find and compare flights from Chicago to St. John's that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 6/19

10:25 am-12:35 am

1 stop11h 40m

St John's

Sat 6/27

6:00 am-9:40 am

2 stops30h 10m

$551

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 6/6

10:15 am-12:56 am

2 stops12h 11m

St John's

Thu 6/11

7:00 pm-9:35 am

1 stop17h 05m

$558

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 9/1

3:20 pm-12:55 am

2 stops7h 05m

St John's

Wed 9/16

1:45 pm-9:35 pm

2 stops10h 20m

$571

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 9/24

7:00 am-10:55 pm

1 stop13h 25m

St John's

Sat 9/26

3:00 pm-2:35 pm

1 stop26h 05m

$583

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 9/1

3:20 pm-10:55 pm

1 stop29h 05m

St John's

Wed 9/16

7:00 pm-11:00 am

1 stop18h 30m

$606

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Mon 7/6

3:20 pm-12:55 am

2 stops7h 05m

St John's

Thu 7/9

6:05 am-2:35 pm

2 stops11h 00m

$613

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 8/26

3:20 pm-12:55 am

2 stops7h 05m

St John's

Sun 8/30

6:05 am-2:35 pm

2 stops11h 00m

$613

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 9/30

8:45 am-5:08 pm

1 stop5h 53m

St John's

Sat 10/10

5:35 am-1:10 pm

2 stops10h 05m

$646

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 8/19

3:20 pm-12:55 am

2 stops7h 05m

St John's

Wed 8/26

6:05 am-2:35 pm

2 stops11h 00m

$661

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Thu 6/11

10:15 am-12:56 am

2 stops12h 11m

St John's

Wed 6/17

6:00 am-9:40 am

2 stops30h 10m

$662

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-St. John's flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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
No data available for this route at this time. Please check back soon.

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 May 12, 2026.
Read reviews from past customers who have flown 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.
Air Canada
7.1
Good
11,026 reviews

Boarding

7.3

Crew

7.8

Overall

7.1

Comfort

7.1

Food

6.3

Entertainment

6.8

Reviews

1 / 20
8.0
Excellent

Dr vandana,Feb 2026

SFO - YYC

It was good, the lounge facilities can be better with some vegetarian options. Overall good
Air Canada
7.1
Good
11,026 reviews
Air Canada
7.1
Good
11,026 reviews

Boarding

7.3

Crew

7.8

Overall

7.1

Comfort

7.1

Food

6.3

Entertainment

6.8

Reviews

1 / 20
8.0
Excellent

Dr vandana,Feb 2026

SFO - YYC

It was good, the lounge facilities can be better with some vegetarian options. Overall good

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 5h 53m. 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 ($524) 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
St. Louis to St. John's 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 May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$252Average$677FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$524Average$669FlexibilityNo cancel feeOn-time67%

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