CHI - YYT

$581 Find Cheap Flights from Chicago to St. John's

This is the cheapest round-trip 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 5/20. 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
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Everything you should know

Cheapest round-trip
$581
Air Canada
Wed 5/20Mon 5/25
ORD - YYT • 1 stop
Cheapest one-way
Multiple Airlines
Sat 1/31
CHI - YYT • multi-stop
Top airlines
Air Canada
Cheapest • from $581 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Wed, May 20 - Mon, May 25
Air Canada Logo
3:50 pm - 1:38 am
ORD
-
YYT
7h 18m
1 stop
Air Canada Logo
1:35 pm - 7:25 pm
YYT
-
ORD
8h 20m
1 stop
$581Air Canada
Wed, Jun 24 - Mon, Jun 29
Air Canada Logo
9:50 am - 11:28 pm
ORD
-
YYT
11h 08m
2 stops
Air Canada Logo
7:30 am - 2:55 pm
YYT
-
ORD
9h 55m
2 stops
$620Air Canada
Mon, Feb 16 - Sat, Feb 21
Air Canada Logo
7:15 am - 5:21 pm
ORD
-
YYT
7h 36m
1 stop
Air Canada Logo
6:10 pm - 9:13 am
YYT
-
ORD
17h 33m
1 stop
$659Air Canada
Tue, Jun 30 - Tue, Jul 7
Air Canada Logo
2:00 pm - 12:35 am
ORD
-
YYT
8h 05m
2 stops
Air Canada Logo
5:30 am - 1:10 pm
YYT
-
ORD
10h 10m
2 stops
$660Air Canada
Wed, Jun 24 - Mon, Jun 29
Air Canada Logo
2:15 pm - 11:21 pm
ORD
-
YYT
6h 36m
1 stop
Air Canada Logo
7:30 am - 2:55 pm
YYT
-
ORD
9h 55m
2 stops
$665Air Canada
Mon, Feb 16 - Sat, Feb 21
Porter Airlines Logo
4:15 pm - 3:35 pm
MDW
-
YYT
20h 50m
2 stops
Porter Airlines Logo
6:15 am - 11:55 am
YYT
-
MDW
8h 10m
2 stops
$702Porter Airlines
Mon, Feb 16 - Sat, Feb 21
Multiple Airlines Logo
2:20 pm - 8:47 am
ORD
-
YYT
15h 57m
1 stop
Multiple Airlines Logo
6:15 am - 12:40 am
YYT
-
ORD
20h 55m
2 stops
$708Multiple Airlines
Mon, Feb 16 - Sat, Feb 21
United Airlines Logo
8:50 am - 1:11 am
ORD
-
YYT
13h 51m
2 stops
United Airlines Logo
5:00 am - 2:38 pm
YYT
-
ORD
12h 08m
2 stops
$719United Airlines
Sun, Mar 29 - Thu, Apr 2
Porter Airlines Logo
6:40 pm - 4:45 pm
ORD
-
YYT
19h 35m
1 stop
Porter Airlines Logo
12:40 pm - 7:17 pm
YYT
-
ORD
9h 07m
1 stop
$755Porter Airlines
Wed, Jun 24 - Mon, Jun 29
WestJet Logo
1:05 pm - 6:03 am
MDW
-
YYT
14h 28m
2 stops
WestJet Logo
7:40 pm - 9:51 am
YYT
-
MDW
16h 41m
2 stops
$1,162WestJet
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 Air Canada ($581) and Porter Airlines ($702).

Good to know

Cheapest flight$581
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 $581 for a round-trip ticket.

  • 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.

  • Which is the best airline for flights from Chicago to St. John's, United Airlines or Air Canada?

    The two airlines most popular with KAYAK users for flights from Chicago to St. John's are United Airlines and Air Canada. With an average price for the route of $647 and an overall rating of 7.4, United Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of $702 and an overall rating of 7.1.

  • 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 airlines 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.
7.4
United AirlinesOverall score based on 9216 reviews
7.7Boarding
8.1Crew
6.6Food
7.3Comfort
7.1Entertainment
Airline reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

2.0 MediocreJames, Jan 2026
ORD - MSP
Read more United Airlines reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

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.

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

Information on your arrival and departure airports