Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Saint John to Chicago from C$ 348

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Saint John to Chicago departing on 13/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Saint John to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
11:05 a.m. - 8:16 p.m.
YSJ
-
ORD
11h 11m
2 stops
Air Canada Logo
4:00 p.m. - 11:54 p.m.
ORD
-
YSJ
5h 54m
1 stop
C$ 709Air Canada
Mon, 2 Nov - Wed, 4 Nov
Air Canada Logo
11:05 a.m. - 8:16 p.m.
YSJ
-
ORD
11h 11m
2 stops
Air Canada Logo
4:00 p.m. - 11:54 p.m.
ORD
-
YSJ
5h 54m
1 stop
C$ 710Air Canada
Mon, 2 Nov - Wed, 4 Nov
Air Canada Logo
4:30 p.m. - 8:05 p.m.
YSJ
-
ORD
5h 35m
1 stop
Air Canada Logo
8:45 a.m. - 3:50 p.m.
ORD
-
YSJ
5h 05m
1 stop
C$ 730Air Canada
Thu, 27 Aug - Mon, 31 Aug
Air Canada Logo
4:30 p.m. - 8:05 p.m.
YSJ
-
ORD
5h 35m
1 stop
Air Canada Logo
8:45 a.m. - 3:50 p.m.
ORD
-
YSJ
5h 05m
1 stop
C$ 731Air Canada
Thu, 27 Aug - Mon, 31 Aug
Air Canada Logo
5:25 a.m. - 7:35 p.m.
YSJ
-
ORD
16h 10m
1 stop
Air Canada Logo
4:00 p.m. - 11:54 p.m.
ORD
-
YSJ
5h 54m
1 stop
C$ 765Air Canada
Mon, 2 Nov - Wed, 4 Nov
Air Canada Logo
5:25 a.m. - 12:56 p.m.
YSJ
-
ORD
9h 31m
1 stop
Air Canada Logo
4:00 p.m. - 11:54 p.m.
ORD
-
YSJ
5h 54m
1 stop
C$ 768Air Canada
Mon, 2 Nov - Wed, 4 Nov
Air Canada Logo
11:05 a.m. - 8:16 p.m.
YSJ
-
ORD
11h 11m
2 stops
Air Canada Logo
11:45 a.m. - 11:54 p.m.
ORD
-
YSJ
10h 09m
2 stops
C$ 793Air Canada
Mon, 2 Nov - Wed, 4 Nov
Air Canada Logo
11:05 a.m. - 8:16 p.m.
YSJ
-
ORD
11h 11m
2 stops
Air Canada Logo
11:45 a.m. - 11:54 p.m.
ORD
-
YSJ
10h 09m
2 stops
C$ 794Air Canada
Mon, 2 Nov - Wed, 4 Nov
United Airlines Logo
4:30 p.m. - 8:05 p.m.
YSJ
-
ORD
5h 35m
1 stop
United Airlines Logo
6:00 a.m. - 3:50 p.m.
ORD
-
YSJ
7h 50m
2 stops
C$ 814United Airlines
Thu, 27 Aug - Mon, 31 Aug
United Airlines Logo
4:30 p.m. - 11:22 p.m.
YSJ
-
ORD
8h 52m
2 stops
United Airlines Logo
6:00 a.m. - 3:50 p.m.
ORD
-
YSJ
7h 50m
2 stops
C$ 821United Airlines
Thu, 27 Aug - Mon, 31 Aug

Air Canada flights from Saint John to Chicago

Our best Air Canada deals on Saint John to Chicago flight tickets
Air Canada
2 Nov
YSJ11:05 a.m.Saint John
11h 11m
2 stops
ORD8:16 p.m.Chicago O'Hare Intl
4 Nov
ORD4:00 p.m.Chicago O'Hare Intl
5h 54m
1 stop
YSJ11:54 p.m.Saint John
C$ 709
Air Canada
2 Nov
YSJ11:05 a.m.Saint John
11h 11m
2 stops
ORD8:16 p.m.Chicago O'Hare Intl
4 Nov
ORD4:00 p.m.Chicago O'Hare Intl
5h 54m
1 stop
YSJ11:54 p.m.Saint John
C$ 710
Air Canada
27 Aug
YSJ4:30 p.m.Saint John
5h 35m
1 stop
ORD8:05 p.m.Chicago O'Hare Intl
31 Aug
ORD8:45 a.m.Chicago O'Hare Intl
5h 05m
1 stop
YSJ3:50 p.m.Saint John
C$ 730

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
27 Aug
YSJ4:30 p.m.Saint John
5h 35m
1 stop
ORD8:05 p.m.Chicago O'Hare Intl
31 Aug
ORD6:00 a.m.Chicago O'Hare Intl
7h 50m
2 stops
YSJ3:50 p.m.Saint John
C$ 814
United Airlines
27 Aug
YSJ4:30 p.m.Saint John
8h 52m
2 stops
ORD11:22 p.m.Chicago O'Hare Intl
31 Aug
ORD6:00 a.m.Chicago O'Hare Intl
7h 50m
2 stops
YSJ3:50 p.m.Saint John
C$ 821
United Airlines
27 Aug
YSJ5:00 a.m.Saint John
10h 13m
2 stops
ORD1:13 p.m.Chicago O'Hare Intl
31 Aug
ORD3:00 p.m.Chicago O'Hare Intl
8h 25m
2 stops
YSJ1:25 a.m.Saint John
C$ 836

momondo Fare Finder

 
Customize your flight search to find flights from Saint 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, momondo users made 96,600 searches. Data last updated 31 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

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 2/11

11:05 a.m.-8:16 p.m.

2 stops11h 11m

Chicago O'Hare Intl

Wed 4/11

4:00 p.m.-11:54 p.m.

1 stop5h 54m

C$ 709

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 2/11

11:05 a.m.-8:16 p.m.

2 stops11h 11m

Chicago O'Hare Intl

Wed 4/11

4:00 p.m.-11:54 p.m.

1 stop5h 54m

C$ 710
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 27/8

4:30 p.m.-8:05 p.m.

1 stop5h 35m

Chicago O'Hare Intl

Mon 31/8

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

1 stop5h 05m

C$ 730

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 27/8

4:30 p.m.-8:05 p.m.

1 stop5h 35m

Chicago O'Hare Intl

Mon 31/8

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

1 stop5h 05m

C$ 731

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 2/11

5:25 a.m.-7:35 p.m.

1 stop16h 10m

Chicago O'Hare Intl

Wed 4/11

4:00 p.m.-11:54 p.m.

1 stop5h 54m

C$ 765

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 2/11

5:25 a.m.-12:56 p.m.

1 stop9h 31m

Chicago O'Hare Intl

Wed 4/11

4:00 p.m.-11:54 p.m.

1 stop5h 54m

C$ 768

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 2/11

11:05 a.m.-8:16 p.m.

2 stops11h 11m

Chicago O'Hare Intl

Wed 4/11

11:45 a.m.-11:54 p.m.

2 stops10h 09m

C$ 793

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 2/11

11:05 a.m.-8:16 p.m.

2 stops11h 11m

Chicago O'Hare Intl

Wed 4/11

11:45 a.m.-11:54 p.m.

2 stops10h 09m

C$ 794

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 27/8

4:30 p.m.-8:05 p.m.

1 stop5h 35m

Chicago O'Hare Intl

Mon 31/8

6:00 a.m.-3:50 p.m.

2 stops7h 50m

C$ 814

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 27/8

4:30 p.m.-11:22 p.m.

2 stops8h 52m

Chicago O'Hare Intl

Mon 31/8

6:00 a.m.-3:50 p.m.

2 stops7h 50m

C$ 821

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Saint John to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Saint John to Chicago?

Air Canada and United Airlines are the most popular carriers operating from Saint John to Chicago

When to book flights from Saint John to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Saint John to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Saint John to Chicago (YSJ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Saint John to Chicago

Fastest flight time

5h 35m

Direct flights

None
The fastest flight from Saint John to Chicago takes 5h 35m
There are no direct flights from Saint John to Chicago. There are no popular flight routes from Saint John to Chicago.
Search flight deals

Frequently asked questions about flying from Saint John to Chicago

  • How far is Saint John to Chicago by plane?

    Chicago is 1770.5 km away from Saint John. By plane, this route typically takes 5h 35m.

  • When did momondo last update prices for flights from Saint John Airport to Chicago?

    Prices for flights from Saint John Airport to Chicago are updated daily.

  • How old do you have to be to fly from Saint John Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Saint John Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

Why use momondo?

Why should I use momondo to find a flight deal from Saint John to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Saint John to Chicago for you.

Can I find flights from Saint John to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Saint John which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Saint John to Chicago?

Once you have performed a search for Saint John to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Saint John to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Saint John. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 30/6
Tue 7/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport