Cheap Flights from St John's to Chicago

Compare St John's to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from St John's to Chicago

Looking for a cheap last-minute deal or the best return flight from St John's to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from St John's to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like St John's to Chicago flights are currently cheapest in May.

St John's to Chicago: Flight information

The things to know before you go.
Cheapest flight found$792
Cheapest month to flyMay

Finding cheap flights from St John's to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from St John's to Chicago is $792. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from St John's to Chicago. But we found flights with one or more stops from $792.
As of February 2026, there are no flights flying from St John's to Chicago.
The cheapest month to fly from St John's to Chicago is usually May.
If you're flying from St John's Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $792.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from St John's Airport to Chicago on Wednesday, 20 May 2026.
No airlines currently offer direct flights between St John's Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Air Canada offers the cheapest flight tickets to Chicago.

Travelling from St. John's International Airport (YYT) to Chicago: what you need to know

  • St. John's International Airport is located in St John's. Based in the UTC-5 timezone, Chicago is two hours 30 minutes behind St John's.

  • To avoid rushing for your YYT to Chicago flight, allow plenty of time to navigate the airport and find your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the standard rule.

  • Heading away during a peak time like a bank holiday? Expect longer lines at check-in and security. To give yourself peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

  • The journey from central St John's to YYT takes around 1 hour by public transport. If you drive, ride-share or get a cab, you'll cover the 6 kilometres in 15 minutes or so, depending on traffic.

  • Searching for a hotel close to YYT? If you're catching an early flight from St. John's International Airport to Chicago, these stays will put you moments from check-in:

  • When it comes to St. John's International Airport's on-time performance, data shows 62.67% of flights arrive within the scheduled time frame.

How to find the cheapest flights from St. John's International Airport (YYT) to Chicago

  • The lowest price we've found for a one-way St. John's International Airport to Chicago flight is $442. The cheapest price for a return flight is $792. Keep in mind fares may change due to demand at the time of booking.

  • Booking in advance is often the key to securing a cheap flight from YYT to Chicago. Flight prices rise as demand increases, so the nearer your departure date, the more it could cost you.

  • Scoring cheap tickets from St. John's International Airport to Chicago is easier if you're flexible with your travel plans. Try using the 'Whole month' search tool to access the lowest fares throughout the month and pick up an awesome deal.

  • Finding a cheap flight from YYT to Chicago is a breeze with Price Alerts. Simply set up one of these automatic notifications and we'll notify you when a better deal is available.

  • Save on your flight from St. John's International Airport to Chicago with the help of our filters. Choose your preferred departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're getting a cab or a ride-share, the drive takes about 35 minutes.

  • It'll take around 55 minutes to get there by public transport.

  • If you're coming in on a late flight from St. John's International Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and snoozing soon after at one of these accommodation options near ORD:

  • Say yes to new adventures by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's main sights.

  • Get the best deal by reserving your ride from O'Hare International Airport about four weeks ahead of your flight from YYT to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from St. John's International Airport to Chicago has landed, you can get to the city centre in about 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • Travelling by public transport will take about 45 minutes.

  • After stepping off your YYT to Chicago flight, rest your head at a hotel close to MDW. These are some great accommodation options that'll help you switch to relaxation mode:

  • No time to waste? The fastest way to get to where you're going is with a Chicago Midway International Airport rental car. Collect a set of wheels from Dollar, Hertz or Budget and make a speedy getaway.

  • Lock in the lowest price by securing your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 137 kilometres from central Chicago. It'll take you about 1 hour 25 minutes to reach the city centre by ride-share or cab after your flight from St. John's International Airport to Chicago.

  • If you use public transport, expect a journey of about 4 hours 15 minutes.

  • If you don't want to make the journey into the centre, choose a hotel close to RFD. Make yourself comfortable at one of these stays after your YYT to Chicago flight:

  • Start your trip without stressing over how to get to your destination with a Chicago Rockford International Airport rental car. Find your perfect set of wheels with trusted names here like Budget, Alamo and National.

  • Booking at least a few weeks ahead of your flight from St. John's International Airport to Chicago is a good move. As well as better prices, you'll get a better selection of vehicle makes and models at RFD.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your travel dates before securing your flight from St. John's International Airport to Chicago. The city buzzes in high season, but prices are generally higher and major attractions can be crowded. Go to Chicago in the low season if you want a quieter vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your St. John's International Airport to Chicago flight ticket then if that's your ideal forecast.

  • January has average temperatures of between -12ºC and 3ºC. Look for a cheap ticket from YYT to Chicago around that time if you like cooler conditions.

More about Chicago

Explore more of United States

  • You've visited Chicago, now it's time to explore other corners of United States. Journey about 451 kilometres south-east to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a full itinerary ahead.

  • If there's time to check out another side of United States, consider Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.