$438+ Cheap flights from Chicago (CHI) to Saint John (YSJ)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YSJ
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to St John with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to St John
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Best
Last-minute
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Cheapest flights from Chicago to St JohnExplore the most affordable flight options available from Chicago to St John. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
Explore the most affordable flight options available from Chicago to St John. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
This Air Canada deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:52 pm -
1 stop6h 59m
Sat 10/245:00 am -
1 stop6h 48m
Deal found 9/18![Multiple Airlines logo]()
$635
This Air Canada deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:52 pm -
1 stop6h 59m
Sun 10/115:00 am -
1 stop6h 48m
Deal found 9/19![Multiple Airlines logo]()
$658
This Air Canada deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:57 pm -
1 stop7h 27m
Mon 10/265:15 am -
1 stop6h 29m
Deal found 9/21![Multiple Airlines logo]()
$713
This Air Canada deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:11 am -
1 stop6h 48m
Sun 10/115:00 am -
1 stop6h 48m
Deal found 9/19![Multiple Airlines logo]()
$923
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:39 am -
2 stops10h 49m
Tue 11/1011:05 am -
1 stop5h 47m
Deal found 9/18![United Airlines logo]()
$939
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:00 am -
2 stops16h 24m
Mon 10/265:15 am -
1 stop6h 29m
Deal found 9/21![United Airlines logo]()
$944
Best flights from Chicago to St JohnDiscover carefully curated flight deals from Chicago to St John that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Chicago to St John that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This Air Canada deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:47 pm -
1 stop5h 37m
Wed 11/115:20 am -
1 stop6h 24m
Deal found 9/20![Multiple Airlines logo]()
$713
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 am -
2 stops8h 59m
Thu 11/1211:05 am -
1 stop5h 47m
Deal found 9/21![United Airlines logo]()
$939
This Air Canada deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:57 pm -
1 stop7h 27m
Thu 11/125:20 am -
1 stop6h 24m
Deal found 9/21![Multiple Airlines logo]()
$713
This United deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:11 am -
1 stop6h 48m
Sat 10/245:00 am -
2 stops11h 52m
Deal found 9/18![Multiple Airlines logo]()
$805
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:00 am -
2 stops9h 54m
Wed 11/1111:05 am -
1 stop5h 47m
Deal found 9/20![United Airlines logo]()
$939
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:39 am -
2 stops10h 49m
Tue 11/1011:05 am -
1 stop5h 47m
Deal found 9/18![United Airlines logo]()
$939
This Air Canada deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:11 am -
1 stop6h 48m
Sun 10/115:00 am -
1 stop6h 48m
Deal found 9/19![Multiple Airlines logo]()
$923
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:00 am -
2 stops16h 24m
Mon 10/265:15 am -
1 stop6h 29m
Deal found 9/21![United Airlines logo]()
$944
Last-minute flights from Chicago to St JohnDiscover last-minute flight deals from Chicago to St John. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St John. Data last updated September 22, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/294:33 pm -
1 stop5h 18m
Sun 10/45:00 am -
1 stop6h 00m
Deal found 9/22![Multiple Airlines logo]()
$1,232
This Air Canada deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:11 am -
1 stop6h 48m
Sun 10/115:00 am -
1 stop6h 48m
Deal found 9/19![Multiple Airlines logo]()
$923
This Air Canada deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:52 pm -
1 stop6h 59m
Sun 10/115:00 am -
1 stop6h 48m
Deal found 9/19![Multiple Airlines logo]()
$658
This Air Canada deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:52 pm -
1 stop6h 59m
Sat 10/245:00 am -
1 stop6h 48m
Deal found 9/18![Multiple Airlines logo]()
$635
This Air Canada deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:57 pm -
1 stop7h 27m
Mon 10/265:15 am -
1 stop6h 29m
Deal found 9/21![Multiple Airlines logo]()
$713
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:00 am -
2 stops16h 24m
Mon 10/265:15 am -
1 stop6h 29m
Deal found 9/21![United Airlines logo]()
$944
One-way flights from Chicago to St JohnSearch for one-way flight options from Chicago to St John. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Chicago to St John. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Air Canada deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/304:30 pm -
1 stop4h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Air Canada logo]()
$438
This Air Canada deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:05 am -
1 stop25h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Air Canada logo]()
$463
This Air Canada deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/312:50 pm -
2 stops19h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Air Canada logo]()
$491
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/19:49 pm -
2 stops10h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$652
Find flight deals from Chicago to St John
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to St John (YSJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 22, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $635 (Air Canada) |
One-way from | $438 (Air Canada) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to St John that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 22, 2026.
Use the filters below to find and compare flights from Chicago to Saint John that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Mon 1/4
10:05 am-4:54 pm
1 stop4h 49m
Saint John
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$438
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Tue 12/29
7:05 am-10:25 am
1 stop25h 20m
Saint John
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$463
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Wed 12/30
4:30 pm-10:25 am
2 stops15h 55m
Saint John
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$476
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Thu 12/31
4:30 pm-10:25 am
2 stops15h 55m
Saint John
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$476
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Fri 1/1
9:49 pm-10:25 am
2 stops10h 36m
Saint John
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$652
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Wed 11/4
3:47 pm-11:24 pm
1 stop5h 37m
Saint John
Wed 11/11
5:20 am-9:44 am
1 stop6h 24m
$713
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Thu 11/5
1:57 pm-11:24 pm
1 stop7h 27m
Saint John
Thu 11/12
5:20 am-9:44 am
1 stop6h 24m
$713
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Wed 10/21
7:11 am-3:59 pm
1 stop6h 48m
Saint John
Sat 10/24
5:00 am-2:52 pm
2 stops11h 52m
$805
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Fri 10/2
7:11 am-3:59 pm
1 stop6h 48m
Saint John
Sun 10/11
5:00 am-9:48 am
1 stop6h 48m
$923
ChicagoSaint John
ORD Chicago O'Hare Intl - YSJ Saint John
ORDYSJ
Chicago O'Hare Intl
Thu 11/5
5:55 am-4:54 pm
2 stops8h 59m
Saint John
Thu 11/12
11:05 am-2:52 pm
1 stop5h 47m
$939
Showing 1-10 of 13 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Chicago-Saint John flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago-Saint John flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Chicago-Saint John flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Saint John flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Saint John flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to St John
Have a flexible travel schedule? Discover the best time to fly to St John from Chicago with our price prediction graph.
CHI-YSJ
ORD-YSJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Saint John
CHI-YSJ
ORD-YSJ
No data available for this route at this time. Please check back soon.
Related info for your journey
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