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Cheap flights from Saint John to Chicago from C$ 310

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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
YSJ — CHI
5 Aug — 12 Aug1
1 adult

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 31 July 2025.

Round-trip from

C$ 534

One-way from

C$ 310
Air Canada
  • Air Canada
  • 12/9-19/9
  • 2 total stops
  • 11h 41m total
  • Saint John to Chicago
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Air Canada
  • Air Canada
  • 3/9
  • 1 total stop
  • 6h 58m total
  • Saint John to Chicago
Search Deals

Find flight deals from St John to Chicago

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 31 July 2025.

Fri 12/911:35 a.m.YSJ - ORD
1 stop5h 20mAir Canada
Fri 19/93:50 p.m.ORD - YSJ
1 stop6h 21mAir Canada
Deal found 29/7C$ 534
Sun 7/910:45 a.m.YSJ - ORD
3 stops25h 58mMultiple Airlines
Sun 19/1012:05 p.m.ORD - YSJ
2 stops19h 55mMultiple Airlines
Deal found 29/7C$ 665
Sun 14/95:55 a.m.YSJ - ORD
1 stop6h 58mUnited Airlines
Sun 21/98:50 a.m.ORD - YSJ
2 stops13h 21mUnited Airlines
Deal found 31/7C$ 763

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 31 July 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

Fri 12/9

11:35 a.m.-2:55 p.m.

1 stop5h 20m

Chicago O'Hare Intl

Fri 19/9

3:50 p.m.-12:11 a.m.

1 stop6h 21m

C$ 534

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 7/9

10:45 a.m.-10:43 a.m.

3 stops25h 58m

Chicago O'Hare Intl

Sun 19/10

12:05 p.m.-10:00 a.m.

2 stops19h 55m

C$ 665

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 14/9

5:55 a.m.-10:53 a.m.

1 stop6h 58m

Chicago O'Hare Intl

Sun 21/9

8:50 a.m.-12:11 a.m.

2 stops13h 21m

C$ 763

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 3/9

5:55 a.m.-10:53 a.m.

1 stop6h 58m

C$ 310

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 3/9

10:45 a.m.-6:50 p.m.

2 stops34h 05m

C$ 407

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sat 30/8

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

2 stops13h 50m

C$ 419

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 31 July 2025.
Get a feel of what it's like to fly with United Airlines and Air Canada from Saint John to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,902 reviews
Check prices

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,902 reviews
United Airlines
7.4
Good
8,902 reviews
Check prices

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
9,842 reviews
United Airlines
7.4
Good
8,902 reviews
Check prices

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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.

  • 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.

  • What is the cheapest month to book a flight from Saint John to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Saint John to Chicago (average of C$ 261). Flying from Saint John to Chicago in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

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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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