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St. John's

$424+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYT
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
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 October 22, 2025.

This Gotogate deal was found by Cheapflights users on 10/21. 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 11/2111:00 amMDW - YYT
2 stops11h 31mPorter Airlines
Fri 11/286:20 amYYT - MDW
2 stops11h 30mPorter Airlines
Deal found 10/21$424
This Mytrip deal was found by Cheapflights users on 10/21. 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 12/511:00 amMDW - YYT
2 stops11h 33mPorter Airlines
Fri 12/126:20 amYYT - MDW
2 stops11h 30mPorter Airlines
Deal found 10/21$433
This Mytrip deal was found by Cheapflights users on 10/22. 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 12/67:15 amORD - YYT
2 stops15h 18mMultiple Airlines
Sat 12/136:00 amYYT - ORD
3 stops20h 49mMultiple Airlines
Deal found 10/22$437
This FlightHub deal was found by Cheapflights users on 10/21. 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 12/311:00 amMDW - YYT
2 stops9h 45mPorter Airlines
Sat 12/66:20 amYYT - MDW
2 stops8h 00mPorter Airlines
Deal found 10/21$444
This FlightHub deal was found by Cheapflights users on 10/22. 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 stops11h 33mPorter Airlines
Mon 12/156:00 amYYT - MDW
2 stops11h 50mPorter Airlines
Deal found 10/22$468
This Air Canada deal was found by Cheapflights users on 10/21. 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.
Wed 12/33:35 pmORD - YYT
1 stop6h 51mAir Canada
Sat 12/67:30 amYYT - ORD
2 stops9h 55mAir Canada
Deal found 10/21$481
This Air Canada deal was found by Cheapflights users on 10/22. 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 12/123:35 pmORD - YYT
1 stop6h 51mAir Canada
Mon 12/155:05 amYYT - ORD
2 stops12h 35mAir Canada
Deal found 10/22$488
This Mytrip deal was found by Cheapflights users on 10/22. 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 12/58:52 pmORD - YYT
3 stops25h 41mMultiple Airlines
Fri 12/126:00 amYYT - ORD
2 stops17h 49mMultiple Airlines
Deal found 10/22$500
This Mytrip deal was found by Cheapflights users on 10/21. 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.
Wed 12/36:48 amORD - YYT
2 stops15h 45mMultiple Airlines
Sat 12/66:00 amYYT - ORD
3 stops20h 49mMultiple Airlines
Deal found 10/21$510
This Mytrip deal was found by Cheapflights users on 10/21. 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.
Wed 12/31:50 pmMDW - YYT
3 stops23h 15mMultiple Airlines
Sat 12/66:00 amYYT - MDW
2 stops8h 20mMultiple Airlines
Deal found 10/21$573

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$424
(Gotogate)

Popular in

December

Cheapest in

February
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
Highest demand for flights based on searches. 25% potential increase in price ($243 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($37 potential savings vs. average RT price).
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 October 22, 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

MDW - YYT

MDWYYT

Chicago Midway

Fri 12/5

11:00 am-1:03 am

2 stops11h 33m

St John's

Fri 12/12

6:20 am-3:20 pm

2 stops11h 30m

$433

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 12/6

7:15 am-1:03 am

2 stops15h 18m

St John's

Sat 12/13

6:00 am-12:19 am

3 stops20h 49m

$437

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 12/3

11:00 am-11:15 pm

2 stops9h 45m

St John's

Sat 12/6

6:20 am-11:50 am

2 stops8h 00m

$444

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Fri 12/12

11:00 am-1:03 am

2 stops11h 33m

St John's

Mon 12/15

6:00 am-3:20 pm

2 stops11h 50m

$468

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

$481

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Mon 12/15

3:35 pm-12:56 am

1 stop6h 51m

St John's

Mon 12/22

5:05 am-11:18 am

1 stop8h 43m

$481

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 12/3

7:05 am-5:21 pm

1 stop7h 46m

St John's

Sat 12/6

5:05 am-11:18 am

1 stop8h 43m

$481

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Fri 12/5

3:35 pm-12:56 am

1 stop6h 51m

St John's

Fri 12/12

5:05 am-11:18 am

1 stop8h 43m

$481

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 12/23

3:55 pm-1:33 am

1 stop7h 08m

St John's

Mon 12/29

5:05 am-11:18 am

1 stop8h 43m

$488

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 12/3

1:50 pm-3:35 pm

3 stops23h 15m

St John's

Sat 12/6

6:00 am-11:50 am

2 stops8h 20m

$573

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 11 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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

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 October 22, 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 October 22, 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
8,990 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,990 reviews
United Airlines
7.4
Good
8,990 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Air Canada
7.1
Good
10,344 reviews
United Airlines
7.4
Good
8,990 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 46m. 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 ($489), and Air Canada ($498) offers the cheapest pricing from Chicago to St. John's. You may be able to fly from Chicago to St. John's for 29% less than the average price by searching for these airlines.

  • 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.

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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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$489Average$677FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$498Average$671FlexibilityNo cancel feeOn-time67%

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