$334 Cheap flight deals from Chicago (CHI) to Saint John (YSJ)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Airfares from $334 One Way, $939 Round Trip from Chicago to Saint John

Prices starting at $939 for return flights and $334 for one-way flights to Saint John were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 3 - Wed, Sep 9
ORD
Chicago
YSJ
Saint John
$939 Roundtrip, found 3 days ago
$939
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu, Sep 3 from Chicago to Saint John, returning Wed, Sep 9, priced at $939 found 3 days ago
Thu, Sep 3 - Wed, Sep 9
ORD
Chicago
YSJ
Saint John
$963 Roundtrip, found 3 days ago
$963
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu, Sep 3 from Chicago to Saint John, returning Wed, Sep 9, priced at $963 found 3 days ago
Fri, Sep 4 - Sat, Sep 12
ORD
Chicago
YSJ
Saint John
$977 Roundtrip, found 4 days ago
$977
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Sep 4 from Chicago to Saint John, returning Sat, Sep 12, priced at $977 found 4 days ago
Mon, Jan 11 - Mon, Jan 18
ORD
Chicago
YSJ
Saint John
$980 Roundtrip, found 1 day ago
$980
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Jan 11 from Chicago to Saint John, returning Mon, Jan 18, priced at $980 found 1 day ago
Thu, Sep 3 - Wed, Sep 9
ORD
Chicago
YSJ
Saint John
$992 Roundtrip, found 3 days ago
$992
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu, Sep 3 from Chicago to Saint John, returning Wed, Sep 9, priced at $992 found 3 days ago
Fri, Sep 4 - Sat, Sep 12
ORD
Chicago
YSJ
Saint John
$1,000 Roundtrip, found 4 days ago
$1,000
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Sep 4 from Chicago to Saint John, returning Sat, Sep 12, priced at $1,000 found 4 days ago
Mon, Jan 11 - Mon, Jan 18
ORD
Chicago
YSJ
Saint John
$1,003 Roundtrip, found 1 day ago
$1,003
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Jan 11 from Chicago to Saint John, returning Mon, Jan 18, priced at $1,003 found 1 day ago
Thu, Sep 3 - Wed, Sep 9
ORD
Chicago
YSJ
Saint John
$1,015 Roundtrip, found 3 days ago
$1,015
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu, Sep 3 from Chicago to Saint John, returning Wed, Sep 9, priced at $1,015 found 3 days ago

More About Flying To Saint John from Chicago

Route Information for Flights from Chicago to Saint John

Origin Airport IATA Code
CHI
Destination Airport IATA Code
YSJ
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Saint John

Grab great fares on Chicago to Saint John flights with Orbitz, your #1 source for discount international and domestic air tickets. Our cutting-edge mobile tools and great online search functionality make booking your next budget trip a breeze.

Mobile Apps for Exclusive Deals on Flights From Chicago to Saint John

You don’t have to sit down at a computer to find the latest flight bargains. Orbitz offers a mobile app for Android, iPhone, and tablet devices, which will keep you alert to fantastic fares, hotel discounts, and more great savings. The app gives you real-time low fares for flights from Chicago to Saint John and lets you book your hotel room with a few simple clicks.

Find Your Chicago to Saint John Flights, Car, and Hotel in One Place

Orbitz gives you the latest deals on air fares, hotels, cruises, and car rentals at up to 50% off. Booking your flights from Chicago to Saint John is easy whether you are using a computer, with the Orbitz mobile app, or through m.orbitz.com on your mobile device’s Web browser.

Stay Informed on Your Trip

Orbitz sends you alerts about the latest updates to your Chicago to Saint John flights, such as delays. Receive the updates via your email or mobile phone. Use the Orbitz app to stay updated on your flight status and baggage claim details.

Earn Miles for Flights From Chicago to Saint John

On qualified flights, add your frequent flyer number to your booking to get miles or points for your trip.

Frequently asked questions

What is the shortest flight from Chicago to Saint John?
From Chicago, the eclectic sights and sounds of Saint John are at least 3 hours and 20 minutes away. Lock in your favorite seat, or maybe even upgrade to one with a little more legroom, and get to your destination in pure comfort.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.