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St. John's

$255+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
Apr 12 — Apr 191
Sun 4/12
Sun 4/19
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 March 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/257:30 am
MDW
-
YYT
2 stops15h 01m
Multiple Airlines
Mon 5/41:20 pm
YYT
-
MDW
1 stop22h 50m
Multiple Airlines
Deal found 3/10$490
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:55 am
ORD
-
YYT
2 stops14h 36m
Multiple Airlines
Tue 4/216:20 am
YYT
-
ORD
2 stops15h 35m
Multiple Airlines
Deal found 3/12$522
This Gotogate deal was found by Cheapflights users on 3/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:50 am
ORD
-
YYT
2 stops11h 08m
Air Canada
Mon 5/42:00 pm
YYT
-
ORD
1 stop8h 38m
Air Canada
Deal found 3/10$529
This Gotogate deal was found by Cheapflights users on 3/12. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:55 am
ORD
-
YYT
2 stops13h 03m
Air Canada
Tue 4/216:35 am
YYT
-
ORD
1 stop9h 00m
Air Canada
Deal found 3/12$536
This Booking.com deal was found by Cheapflights users on 3/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:20 pm
MDW
-
YYT
2 stops7h 06m
Porter Airlines
Thu 5/286:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 3/8$552
This FlightHub deal was found by Cheapflights users on 3/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:20 pm
ORD
-
YYT
2 stops7h 05m
Porter Airlines
Sun 9/136:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 3/8$557
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:45 am
ORD
-
YYT
2 stops10h 40m
Porter Airlines
Sun 9/131:45 pm
YYT
-
ORD
2 stops10h 20m
Porter Airlines
Deal found 3/12$563
This FlightHub deal was found by Cheapflights users on 3/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:25 am
MDW
-
YYT
2 stops12h 00m
Porter Airlines
Sun 8/306:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 3/10$568
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1310:25 am
MDW
-
YYT
2 stops12h 01m
Porter Airlines
Mon 6/226:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 3/12$570
This Gotogate deal was found by Cheapflights users on 3/11. 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 Gotogate 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 9/276:05 am
YYT
-
ORD
2 stops11h 00m
Porter Airlines
Deal found 3/11$571
This Gotogate deal was found by Cheapflights users on 3/8. 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.
Sat 6/2010:25 am
MDW
-
YYT
2 stops12h 00m
Porter Airlines
Sun 6/286:05 am
YYT
-
MDW
2 stops11h 00m
Porter Airlines
Deal found 3/8$576
This Air Canada deal was found by Cheapflights users on 3/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/23:45 pm
ORD
-
YYT
1 stop7h 33m
Air Canada
Wed 6/35:35 am
YYT
-
ORD
2 stops10h 05m
Air Canada
Deal found 3/12$600

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 March 13, 2026.

Round-trip from

$490
(Kiwi.com)

One-way from

$255
(Trip.com)
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 March 13, 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

Sat 6/20

10:25 am-12:55 am

2 stops12h 00m

St John's

Sun 6/28

6:05 am-2:35 pm

2 stops11h 00m

$576

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

$580

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 4/24

4:05 pm-11:05 pm

2 stops28h 30m

St John's

Fri 5/1

6:05 am-2:35 pm

2 stops11h 00m

$602

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Mon 8/3

10:25 am-12:55 am

2 stops12h 00m

St John's

Mon 8/10

6:05 am-2:35 pm

2 stops11h 00m

$607

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 8/26

8:45 am-7:43 pm

2 stops8h 28m

St John's

Sun 8/30

5:35 am-1:10 pm

2 stops10h 05m

$610

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 4/25

12:55 pm-11:05 pm

2 stops7h 40m

St John's

Mon 5/4

6:05 am-2:35 pm

2 stops11h 00m

$627

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 5/13

8:45 am-7:43 pm

2 stops8h 28m

St John's

Sat 5/16

5:35 am-1:25 pm

2 stops10h 20m

$628
Quickest round-trip

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 4/24

2:00 pm-11:13 pm

1 stop6h 43m

St John's

Fri 5/1

8:30 am-1:25 pm

1 stop7h 25m

$630

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sat 8/1

10:25 am-12:55 am

2 stops12h 00m

St John's

Sun 8/9

6:05 am-2:35 pm

2 stops11h 00m

$631

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Thu 6/11

8:45 am-11:28 pm

2 stops12h 13m

St John's

Fri 6/19

5:35 am-10:16 am

1 stop7h 11m

$670

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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 March 13, 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
10,800 reviews

Food

6.3

Overall

7.1

Boarding

7.3

Crew

7.8

Comfort

7.1

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
10,800 reviews
Air Canada
7.1
Good
10,800 reviews

Food

6.3

Overall

7.1

Boarding

7.3

Crew

7.8

Comfort

7.1

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 8h 28m. 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 ($225), 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

Browse thousands of different options on Cheapflights for your next trip

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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 March 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$225Average$602FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$524Average$661FlexibilityNo cancel feeOn-time67%

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