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Cheap flights from Saint John to Chicago from C$ 449

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
YSJ — CHI
21 Jun — 28 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from St John to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from St John to Chicago
Explore the most affordable flight options available from St John to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 May 2026.

Wed 14/104:30 p.m.
YSJ
-
ORD
1 stop5h 42m
Air Canada
Sat 17/108:45 a.m.
ORD
-
YSJ
1 stop5h 04m
Air Canada
Deal found 21/5C$ 704
Fri 10/710:45 a.m.
YSJ
-
ORD
1 stop8h 12m
Multiple Airlines
Thu 16/78:45 a.m.
ORD
-
YSJ
2 stops23h 15m
Multiple Airlines
Deal found 22/5C$ 706
Mon 23/1111:05 a.m.
YSJ
-
ORD
1 stop5h 50m
Air Canada
Fri 27/114:00 p.m.
ORD
-
YSJ
1 stop5h 54m
Air Canada
Deal found 17/5C$ 711
Fri 10/74:40 p.m.
YSJ
-
ORD
1 stop5h 25m
Air Canada
Thu 16/77:25 a.m.
ORD
-
YSJ
1 stop14h 25m
Air Canada
Deal found 22/5C$ 762
Sun 21/65:40 a.m.
YSJ
-
ORD
1 stop5h 20m
Air Canada
Wed 24/68:40 p.m.
ORD
-
YSJ
1 stop13h 15m
Air Canada
Deal found 22/5C$ 866
Fri 10/75:00 a.m.
YSJ
-
MDW
1 stop11h 35m
Multiple Airlines
Thu 16/710:20 a.m.
MDW
-
YSJ
2 stops10h 55m
Multiple Airlines
Deal found 22/5C$ 1,224
Sun 21/66:55 a.m.
YSJ
-
MDW
3 stops31h 51m
Multiple Airlines
Wed 24/610:25 a.m.
MDW
-
YSJ
2 stops34h 50m
Multiple Airlines
Deal found 22/5C$ 1,405

Find flight deals from St John to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from St John (YSJ) to Chicago (CHI). 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 22 May 2026.

Round-trip from

C$ 704

One-way from

C$ 449
Air Canada
  • Air Canada
  • 14/10-17/10
  • 2 total stops
  • 10h 46m total
  • Saint John to Chicago
Search Deals
Air Canada
  • Air Canada
  • 6/7
  • 1 total stop
  • 6h 00m total
  • Saint John to Chicago
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from St John to Chicago 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 629,999 searches. Data last updated 22 May 2026.
Use the filters below to find and compare flights from Saint John to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 14/10

4:30 p.m.-8:12 p.m.

1 stop5h 42m

Chicago O'Hare Intl

Sat 17/10

8:45 a.m.-3:49 p.m.

1 stop5h 04m

C$ 704

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 9/6

5:35 a.m.-9:00 a.m.

1 stop5h 25m

Chicago O'Hare Intl

Thu 16/7

11:07 a.m.-11:50 p.m.

2 stops10h 43m

C$ 1,161

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 21/6

5:40 a.m.-11:26 p.m.

2 stops19h 46m

Chicago O'Hare Intl

Wed 24/6

7:00 a.m.-11:50 p.m.

2 stops14h 50m

C$ 1,213

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Fri 10/7

5:00 a.m.-2:35 p.m.

1 stop11h 35m

Chicago Midway

Thu 16/7

10:20 a.m.-11:15 p.m.

2 stops10h 55m

C$ 1,224

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Sun 21/6

6:55 a.m.-9:40 a.m.

2 stops28h 45m

Chicago Midway

Wed 24/6

10:25 a.m.-11:15 p.m.

2 stops34h 50m

C$ 1,440
Cheapest one-way
Quickest one-way

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 6/7

5:00 a.m.-9:00 a.m.

1 stop6h 00m

C$ 449

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 6/7

10:45 a.m.-10:10 a.m.

2 stops25h 25m

C$ 497

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Mon 6/7

10:45 a.m.-9:08 a.m.

2 stops24h 23m

C$ 508

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/5

Sorted by cheapest first

Best time to book a flight from St John to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St John with our price prediction graph.
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 Saint John to Chicago
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from St John to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Saint John to Chicago?

    Saint John (YSJ) is the airport you will fly out of if you book a flight from Saint John to Chicago. You should not have trouble finding flights to Chicago from Saint John; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Saint John airport to Chicago. It is only a 15.1 km journey to Saint John (YSJ) from Saint John’s city centre.

  • How long is the flight from Saint John to Chicago?

    A quick flight from Saint John to Chicago can take about 5h 42m. Air Canada provides one of the quickest options available for as low as C$ 704. Saint John and Chicago are separated by a distance of 1802 km.

  • Can I find deals for flights from St John to Chicago that include hotel bookings?

    Yes. In addition to deals on St John to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from St John to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St John to Chicago.

  • Can I find deals for business class flights from St John to Chicago?

    Yes. Cheapflights offers flight deals from St John to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for St John to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Moncton to O'Hare Intl flights
St John to O'Hare Intl flights

Fly with Cheapflights

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How does Cheapflights help users find flights from St John to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from St John to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from St John to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from St John.

Can Cheapflights find flights from St John to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from St John to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from St John to Chicago become cheaper?

Yes! Start tracking prices for St John to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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