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Cheap flights from Saint John to Chicago from C$ 693

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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
YSJ — CHI
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

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Best flights from St John to Chicago
Discover carefully curated flight deals from St John to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 30 October 2025.

Tue 7/411:55 a.m.YSJ - ORD
1 stop5h 00mAir Canada
Wed 8/49:50 a.m.ORD - YSJ
1 stop5h 24mAir Canada
Deal found 28/10C$ 693

Cheap 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 30 October 2025.

Round-trip from

C$ 693
Air Canada
  • Air Canada
  • 7/4-8/4
  • 2 total stops
  • 10h 24m total
  • Saint John to Chicago
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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 30 October 2025.
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

Tue 7/4

11:55 a.m.-2:55 p.m.

1 stop5h 00m

Chicago O'Hare Intl

Wed 8/4

9:50 a.m.-5:14 p.m.

1 stop5h 24m

C$ 693

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 7/11

12:00 p.m.-9:19 p.m.

3 stops35h 19m

C$ 1,057

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Fri 7/11

12:00 p.m.-1:07 p.m.

3 stops51h 07m

C$ 1,057

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 7/11

4:15 p.m.-8:00 p.m.

1 stop5h 45m

C$ 1,247

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/10

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. Air Canada provides one of the quickest options available for as low as C$ 693. 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.

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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.
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St John to O'Hare Intl flights

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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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