Find flights
When to book
FAQs

Cheap flights from Saint John to Chicago from C$ 628

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YSJ — CHI
6 Mar — 13 Mar1
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 4 February 2026.

Fri 29/54:30 p.m.
YSJ
-
ORD
1 stop5h 38m
Air Canada
Mon 1/68:45 a.m.
ORD
-
YSJ
1 stop5h 05m
Air Canada
Deal found 2/2C$ 628
Sat 6/612:20 p.m.
YSJ
-
ORD
1 stop7h 58m
United Airlines
Sat 13/69:40 p.m.
ORD
-
YSJ
2 stops16h 10m
United Airlines
Deal found 3/2C$ 709
Sat 14/34:15 p.m.
YSJ
-
ORD
1 stop5h 55m
Air Canada
Tue 17/37:15 a.m.
ORD
-
YSJ
1 stop6h 20m
Air Canada
Deal found 2/2C$ 758
Sat 14/34:15 p.m.
YSJ
-
ORD
1 stop5h 55m
United Airlines
Tue 17/37:40 p.m.
ORD
-
YSJ
2 stops17h 55m
United Airlines
Deal found 2/2C$ 820
Fri 29/54:30 p.m.
YSJ
-
ORD
2 stops9h 00m
United Airlines
Mon 1/611:03 a.m.
ORD
-
YSJ
2 stops10h 49m
United Airlines
Deal found 3/2C$ 953

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 4 February 2026.

Round-trip from

C$ 628
Air Canada
  • Air Canada
  • 29/5-1/6
  • 2 total stops
  • 10h 43m 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 4 February 2026.
Use the filters below to find and compare flights from Saint John to Chicago that are best for you.

Fly from

St John

Fly to

Chicago

Route

Depart

Return

Price

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 29/5

4:30 p.m.-8:08 p.m.

1 stop5h 38m

Chicago O'Hare Intl

Mon 1/6

8:45 a.m.-3:50 p.m.

1 stop5h 05m

C$ 628

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sat 6/6

12:20 p.m.-4:59 p.m.

1 stop6h 39m

Chicago O'Hare Intl

Sat 13/6

8:45 a.m.-3:50 p.m.

1 stop5h 05m

C$ 635

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sat 6/6

12:20 p.m.-6:18 p.m.

1 stop7h 58m

Chicago O'Hare Intl

Sat 13/6

9:40 p.m.-3:50 p.m.

2 stops16h 10m

C$ 709

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sat 14/3

4:15 p.m.-8:10 p.m.

1 stop5h 55m

Chicago O'Hare Intl

Tue 17/3

7:15 a.m.-3:35 p.m.

1 stop6h 20m

C$ 758

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sat 14/3

4:15 p.m.-8:10 p.m.

1 stop5h 55m

Chicago O'Hare Intl

Tue 17/3

7:40 p.m.-3:35 p.m.

2 stops17h 55m

C$ 820

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 29/5

4:30 p.m.-11:30 p.m.

2 stops9h 00m

Chicago O'Hare Intl

Mon 1/6

11:03 a.m.-11:52 p.m.

2 stops10h 49m

C$ 953

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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 38m. Air Canada provides one of the quickest options available for as low as C$ 628. Saint John and Chicago are separated by a distance of 1802 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.