CHI - YYT

$263 Find Cheap Flights from Chicago to St. John's

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to St. John's departing on 5/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to St. John's

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to St. John's, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to St. John's, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$430
Porter Airlines
Mon 5/4Mon 5/11
MDW - YYT • 2 stops
Cheapest one-way
$247
Multiple Airlines
Sat 5/2
ORD - YYT • 2 stops
Top airlines
Porter Airlines
Cheapest • from $465 (round-trip)
Air Canada
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and St. John's. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Toronto (YYZ)
Cheapest • Avg $640 (round-trip)
Montreal (YUL)
Shortest trip • 6h 05m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to St. John's!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to St. John's (CHI-YYT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to St. John's that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to St. John's

Mon, May 4 - Mon, May 11
Multiple Airlines Logo
3:20 pm - 12:56 am
MDW
-
YYT
7h 06m
2 stops
Multiple Airlines Logo
6:00 am - 2:35 pm
YYT
-
MDW
11h 05m
1 stop
$430Multiple Airlines
Thu, Apr 23 - Fri, May 1
Multiple Airlines Logo
11:00 am - 1:01 am
MDW
-
YYT
11h 31m
2 stops
Multiple Airlines Logo
1:20 pm - 9:40 am
YYT
-
MDW
22h 50m
1 stop
$446Multiple Airlines
Thu, Apr 23 - Sat, May 2
Multiple Airlines Logo
11:00 am - 1:01 am
MDW
-
YYT
11h 31m
2 stops
Multiple Airlines Logo
3:00 pm - 2:35 pm
YYT
-
MDW
26h 05m
1 stop
$460Multiple Airlines
Thu, Apr 23 - Fri, May 1
Porter Airlines Logo
11:00 am - 1:01 am
MDW
-
YYT
11h 31m
2 stops
Porter Airlines Logo
6:55 pm - 9:40 am
YYT
-
MDW
17h 15m
1 stop
$465Porter Airlines
Thu, Apr 23 - Fri, May 1
Porter Airlines Logo
11:00 am - 4:45 pm
MDW
-
YYT
27h 15m
1 stop
Porter Airlines Logo
6:55 pm - 9:40 am
YYT
-
MDW
17h 15m
1 stop
$514Porter Airlines
Sat, Sep 12 - Sat, Sep 19
Porter Airlines Logo
11:45 am - 12:55 am
ORD
-
YYT
10h 40m
2 stops
Porter Airlines Logo
6:05 am - 2:35 pm
YYT
-
ORD
11h 00m
2 stops
$563Porter Airlines
Wed, Aug 26 - Sun, Aug 30
Air Canada Logo
3:40 pm - 12:45 am
ORD
-
YYT
6h 35m
1 stop
Air Canada Logo
5:35 am - 10:19 am
YYT
-
ORD
7h 14m
1 stop
$630Air Canada
Wed, Aug 26 - Sun, Aug 30
Air Canada Logo
8:45 am - 5:10 pm
ORD
-
YYT
5h 55m
1 stop
Air Canada Logo
5:35 am - 1:10 pm
YYT
-
ORD
10h 05m
2 stops
$650Air Canada
Wed, Apr 22 - Fri, May 1
Air Canada Logo
8:40 am - 5:21 pm
ORD
-
YYT
6h 11m
1 stop
Air Canada Logo
1:35 pm - 7:25 pm
YYT
-
ORD
8h 20m
1 stop
$655Air Canada
Wed, May 13 - Sat, May 16
Air Canada Logo
8:45 am - 7:43 pm
ORD
-
YYT
8h 28m
2 stops
Air Canada Logo
5:35 am - 1:25 pm
YYT
-
ORD
10h 20m
2 stops
$658Air Canada
Booking Insights

KAYAK's insights & trends for Chicago to St. John's flights

Get data-powered insights and trends into flights from Chicago to St. John's to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Chicago to St. John's?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to St. John's were found on Porter Airlines ($465) and Air Canada ($630).

Find deals

Good to know

Cheapest flight$247
Flight from Chicago O'Hare Airport to St. John's

When to book flights from Chicago to St. John's

Are your dates flexible? Find out the best times to travel from Chicago to St. John's based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to St. John's

  • What is the cheapest flight from Chicago to St. John's?

    In the last 3 days, the lowest price for a flight from Chicago to St. John's was $234 for a one-way ticket and $430 for a round-trip.

  • Do I need a passport to fly between Chicago and St. John's?

    Yes, you’ll need a passport to travel to St. John's from Chicago.

  • Which airports will I be using when flying from Chicago to St. John's?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at St John's.

  • Which aircraft models fly most regularly from Chicago to St. John's?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to St. John's?

    Star Alliance is the only airline alliance operating flights between Chicago and St. John's.

  • How does KAYAK find such low prices on flights from Chicago to St. John's?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to St. John's.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to St. John's?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to St. John's from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to St. John's?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to St. John's with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to St. John's?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to St. John's from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to St. John's

 
See real verified KAYAK customer reviews for airlines flying from Chicago to St. John's. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to St. John's? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 10813 reviews
7.3Boarding
6.8Entertainment
7.1Comfort
7.8Crew
6.3Food
Airline reviews

The crew were fabulous. The flight was bumpy and I always like the captain to tell me what that is about or my imagination gets carries away.

8.0 ExcellentChristiane, Sep 2025
YYZ - YDF
Read more Air Canada reviews

The crew were fabulous. The flight was bumpy and I always like the captain to tell me what that is about or my imagination gets carries away.

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

They went on strike before time and screwed us big time. Which is not fair. We respect their planned strike but why they went on strike ahead of time ??? Poor garbage management

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

Very nice comfortable spacy Airbus 321. I liked the offer of food on the Bistro menu. The idea is very good to pay and cost was low.

Everything you need to know for your flight from Chicago to St. John's

Information on your arrival and departure airports

St. John's (YYT)