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Cheap flights from Saint John to Chicago from C$ 320

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 25/7. Fares are subject to change and may not be available on all flights or dates of travel.
YSJ — CHI
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 578

One-way from

C$ 320
Air Canada
  • Air Canada
  • 20/9-22/9
  • 2 total stops
  • 11h 21m total
  • Saint John to Chicago
Search Deals
25/7
  • 25/7
  • 2 total stops
  • 12h 45m 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 12 June 2025.

Sat 20/911:35 a.m.YSJ - ORD
1 stop5h 20mAir Canada
Mon 22/93:50 p.m.ORD - YSJ
1 stop6h 01mAir Canada
Deal found 11/6C$ 578
Wed 27/811:25 a.m.YSJ - ORD
1 stop5h 30mUnited Airlines
Sun 31/86:00 a.m.ORD - YSJ
2 stops9h 45mUnited Airlines
Deal found 10/6C$ 656
Wed 2/75:55 a.m.YSJ - ORD
1 stop5h 14mMultiple Airlines
Mon 7/78:25 p.m.ORD - YSJ
2 stops12h 24mMultiple Airlines
Deal found 10/6C$ 715

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 12 June 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

Sat 20/9

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

1 stop5h 20m

Chicago O'Hare Intl

Mon 22/9

3:50 p.m.-11:51 p.m.

1 stop6h 01m

C$ 578

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 27/8

11:25 a.m.-2:55 p.m.

1 stop5h 30m

Chicago O'Hare Intl

Sun 31/8

6:00 a.m.-5:45 p.m.

2 stops9h 45m

C$ 656

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 2/7

5:55 a.m.-9:09 a.m.

1 stop5h 14m

Chicago O'Hare Intl

Mon 7/7

8:25 p.m.-10:49 a.m.

2 stops12h 24m

C$ 715

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 25/7

10:45 a.m.-9:30 p.m.

2 stops12h 45m

C$ 320

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 25/7

5:55 a.m.-9:09 a.m.

1 stop5h 14m

C$ 334

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Fri 25/7

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

2 stops25h 00m

C$ 447

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 27/7

6:35 p.m.-2:16 p.m.

2 stops21h 41m

C$ 554

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 12 June 2025.
United Airlines
7.4
Good
8,790 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.0

Boarding

7.7

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
8,790 reviews
United Airlines
7.4
Good
8,790 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.0

Boarding

7.7

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
9,537 reviews
United Airlines
7.4
Good
8,790 reviews
Check prices

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.0

Boarding

7.7

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.
St John to O'Hare Intl flights
Moncton to O'Hare Intl flights

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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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