Cheap flight tickets from Saint John to Chicago

Compare Saint John 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 Saint John to Chicago

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

Find the cheapest month to fly from Saint John to Chicago

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

Saint John to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRM1,076
Cheapest month to flyMay

Finding cheap flights from Saint John 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 Saint John to Chicago is RM2,354. 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 Saint John to Chicago. But we found flights with one or more stops from RM2,354.
As of April 2026, there are no flights flying from Saint John to Chicago.
The cheapest month to fly from Saint John to Chicago is usually April.
If you're flying from Saint John 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 RM2,354.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Saint John Airport to Chicago on Thursday, 30 April 2026.
No airlines currently offer direct flights between Saint John 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 April, the average temperature is usually around 8°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, United offers the cheapest flight tickets to Chicago.

Travelling from Saint John Airport (YSJ) to Chicago: what you need to know

  • Chicago is two hours behind Saint John, where Saint John Airport is located. Chicago follows the UTC-5 timezone.

  • Leave enough time to get on your YSJ to Chicago flight. A good rule of thumb is to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Be prepared for longer queues in popular months like August. Arriving up to four hours in advance for international flights and two hours for domestic departures is a smart move.

  • Located around 14 kilometres from central Saint John, YSJ can be reached in about 20 minutes by car, depending on traffic. Travelling on public transport will take roughly 55 minutes.

  • Booked an early flight from Saint John Airport to Chicago? Avoid the hassle of rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels near YSJ:

  • Of all flights departing from Saint John Airport, 77.05% land on time at their destination.

How to find the cheapest flights from Saint John Airport (YSJ) to Chicago

  • RM1,076 is currently the lowest price for a one-way Saint John Airport to Chicago flight. A return flight ticket starts at RM2,354. These fares can change based on demand and availability.

  • Don't leave everything to the last minute. You're more likely to find cheap flights from YSJ to Chicago if you book ahead. Airlines often offer some amazing early bird deals.

  • The 'Whole month' search tool will show you the cheapest tickets from Saint John Airport to Chicago throughout the entire month. It's a great way to snap up a bargain if your travel plans aren't set in stone.

  • Locking in a cheap flight from YSJ to Chicago is a breeze with Price Alerts. All you need to do is create one of these automatic notifications and we'll get in touch as soon as a cheaper option becomes available.

  • Snag an affordable flight from Saint John Airport to Chicago with the help of our filters. Select your ideal duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you about 35 minutes to reach the centre driving.

  • Travelling to the centre by public transport takes about 55 minutes.

  • If you're arriving on a late flight from Saint John Airport to Chicago, nothing beats the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and sleeping soon after at one of these hotels near ORD:

  • Travel at your own speed with an O'Hare International Airport rental car. Book your wheels from Routes Car Rentals, Dollar or Budget and see more of Chicago and beyond.

  • Booking your ride from O'Hare International Airport about four weeks ahead of your flight from YSJ to Chicago can help you get the best possible rate.

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

Chicago Midway International Airport (MDW)

  • The centre of Chicago is about 19 kilometres from Chicago Midway International Airport (MDW). After your flight from Saint John Airport to Chicago has hit the runway and you've made your way to arrivals, the drive should take about 20 minutes.

  • If you choose to travel on public transport, the journey will take you 45 minutes or so.

  • Following your YSJ to Chicago flight, rest your head at a hotel near MDW. These are some comfortable options that'll help you slip into relaxation mode:

  • Forget about inconvenient public transport schedules or long cab queues. Grab a Chicago Midway International Airport rental car and take your journey in whatever direction you like. Check out the rates and availability from Dollar, Hertz and Budget.

  • Don't pay more than you need to. Booking your ride four weeks before your arrival at MDW can get you a lower rate.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Saint John Airport to Chicago and go straight to your hotel or jump right into sightseeing. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to reach driving.

  • If you go by public transport, the journey takes about 4 hours 15 minutes.

  • Choose a hotel near RFD and go from the plane to your bed in a flash. Whether you're arriving on a late YSJ to Chicago flight or just want a stress-free arrival, these stays bring comfort closer to you:

  • Whether you're looking for an economy for a solo adventure or a full-size SUV to fit a group of friends, you'll find the right Chicago Rockford International Airport rental car for your needs. Explore the range of wheels available from companies such as Budget, Alamo and National.

  • If you prefer a certain type of vehicle, booking early gives you a better shot at finding what you want. Secure your ride from RFD a few weeks ahead of your flight from Saint John Airport to Chicago.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • Before you book your flights from Saint John Airport to Chicago, consider which time of year is best for you. Peak season in Chicago offers a bustling atmosphere and plenty to do, while the low season means you'll get cheaper deals on hotels and smaller crowds.

  • Book a Saint John Airport to Chicago flight ticket with a departure in July if you're eager to experience the city during its warmest month. Expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • If you want cooler conditions, search for a cheap ticket from YSJ to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

  • When it comes to searching for somewhere to rest your head, you'll find the top stays in Chicago right here. Explore these options once you've booked your flight from Saint John Airport to Chicago:

  • There are so many things to discover in this city it can be tricky to know where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top sights which should be on every Chicago itinerary.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If there's time to check out another great destination in 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 among the biggest draws.

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