CHI - YYT

$258 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 9/29. 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.

Flights Deals
Booking Insights
Flights 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, Sep 15 - Mon, Sep 22
 Logo
8:49 pm - 12:38 amORD-YYT
25h 19m2 stops
 Logo
3:40 pm - 4:12 pmYYT-ORD
27h 02m1 stop
Sun, Sep 28 - Thu, Oct 2
 Logo
5:17 pm - 2:30 pmORD-YYT
18h 43m1 stop
 Logo
1:15 pm - 4:12 pmYYT-ORD
29h 27m2 stops
Sun, Sep 28 - Wed, Oct 1
 Logo
5:17 pm - 2:30 pmORD-YYT
18h 43m1 stop
 Logo
6:00 am - 9:58 pmYYT-ORD
18h 28m2 stops
Sun, Sep 28 - Tue, Sep 30
 Logo
5:17 pm - 2:30 pmORD-YYT
18h 43m1 stop
 Logo
6:00 am - 9:58 pmYYT-ORD
18h 28m2 stops
Mon, Sep 15 - Mon, Sep 22
Porter Airlines Logo
9:35 am - 12:38 amMDW-YYT
12h 33m2 stops
Porter Airlines Logo
7:00 am - 4:24 pmYYT-MDW
11h 54m3 stops
$508Porter Airlines
Find Deal
Mon, Sep 15 - Mon, Sep 22
Porter Airlines Logo
5:20 pm - 4:58 pmMDW-YYT
21h 08m3 stops
Porter Airlines Logo
7:00 am - 4:24 pmYYT-MDW
11h 54m3 stops
$514Porter Airlines
Find Deal
Tue, Sep 23 - Wed, Oct 1
Air Canada Logo
8:40 am - 5:09 pmORD-YYT
5h 59m1 stop
Air Canada Logo
5:50 am - 9:51 amYYT-ORD
6h 31m1 stop
$571Air Canada
Find Deal
Tue, Sep 2 - Thu, Sep 11
Air Canada Logo
3:35 pm - 12:39 amORD-YYT
6h 34m1 stop
Air Canada Logo
2:00 pm - 8:11 pmYYT-ORD
8h 41m1 stop
$572Air Canada
Find Deal
Sat, Aug 16 - Mon, Aug 25
United Airlines Logo
2:07 pm - 12:38 amORD-YYT
8h 01m1 stop
United Airlines Logo
5:10 am - 7:29 pmYYT-ORD
16h 49m1 stop
$742United Airlines
Find Deal
Sat, Aug 16 - Mon, Aug 25
United Airlines Logo
8:00 am - 12:38 amORD-YYT
14h 08m2 stops
United Airlines Logo
5:10 am - 7:29 pmYYT-ORD
16h 49m1 stop
$746United Airlines
Find Deal
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$258
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 25% 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 $258 for a one-way ticket and $435 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 $638 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 8904 reviews
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
Airline reviews

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.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

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!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Both flights are delayed so I rate the whole experience as mediocre.

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I had a good experience. I liked being informed about the status of my luggage

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.

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

It was a short flight, and no entertainment. That was not a problem for us, but there is no option for "not applicable". There was a bit of turbulence, so there was no food service.

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.