CHI - YYT

$290 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 9/24. 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

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 22% 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.

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, Oct 1 - Sun, Oct 12
Multiple Airlines Logo
5:17 pm - 12:38 amORD-YYT
28h 51m2 stops
Multiple Airlines Logo
7:10 am - 4:43 pmYYT-ORD
12h 03m1 stop
$432Multiple Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
Porter Airlines Logo
12:45 pm - 1:01 amMDW-YYT
9h 46m2 stops
Porter Airlines Logo
6:20 am - 11:50 amYYT-MDW
8h 00m2 stops
$506Porter Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 5
Multiple Airlines Logo
6:00 am - 1:01 amORD-YYT
16h 31m2 stops
Multiple Airlines Logo
5:40 pm - 9:00 pmYYT-ORD
29h 50m2 stops
$528Multiple Airlines
Find Deal
Wed, Nov 26 - Wed, Dec 10
Multiple Airlines Logo
11:00 am - 1:01 amMDW-YYT
11h 31m2 stops
Multiple Airlines Logo
4:15 pm - 10:05 amYYT-MDW
20h 20m3 stops
$530Multiple Airlines
Find Deal
Wed, Nov 26 - Wed, Dec 10
Multiple Airlines Logo
11:00 am - 11:05 pmMDW-YYT
9h 35m3 stops
Multiple Airlines Logo
4:15 pm - 10:05 amYYT-MDW
20h 20m3 stops
$537Multiple Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 12
Multiple Airlines Logo
7:09 pm - 12:17 pmORD-YYT
38h 38m3 stops
Multiple Airlines Logo
7:10 am - 4:43 pmYYT-ORD
12h 03m1 stop
$543Multiple Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
Air Canada Logo
3:55 pm - 1:33 amORD-YYT
7h 08m1 stop
Air Canada Logo
5:05 am - 3:10 pmYYT-ORD
12h 35m2 stops
$550Air Canada
Find Deal
Tue, Mar 10 - Wed, Mar 11
Air Canada Logo
3:55 pm - 1:33 amORD-YYT
7h 08m1 stop
Air Canada Logo
5:05 am - 3:10 pmYYT-ORD
12h 35m2 stops
$560Air Canada
Find Deal
Wed, Oct 29 - Wed, Nov 5
United Airlines Logo
9:00 am - 12:56 amORD-YYT
13h 26m2 stops
United Airlines Logo
5:05 am - 11:18 amYYT-ORD
8h 43m1 stop
$646United Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
United Airlines Logo
12:45 pm - 12:56 amORD-YYT
9h 41m2 stops
United Airlines Logo
5:00 am - 10:05 amYYT-ORD
7h 35m1 stop
$662United Airlines
Find Deal

Everything you should know

Top airlines
Porter Airlines
Cheapest • from $506 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$432
Multiple Airlines
Wed 10/1Sun 10/12
ORD - YYT • 2 stops
Cheapest one-way
$290
Air Canada
Wed 9/24
ORD - YYT • 2 stops
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!
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.

How much is a round-trip flight from Chicago to St. John's?

Good to know

Low seasonFebruary
Cheapest flight$290
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 24% lower on average.
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 $290 for a one-way ticket and $432 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, and SkyTeam are the airline alliances operating flights between Chicago and St. John's, with Star Alliance being the most commonly used for this route.

  • 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 $704 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 $628 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 8929 reviews
7.7Boarding
8.1Crew
6.6Food
7.3Comfort
7.1Entertainment
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

For the price, it was a really good experience. There was no entertainment on board, so I couldn't really rate this, and I didn't order a meal. I appreciated that there was a free glass of wine.

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

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.