Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Saint John to Chicago from C$ 391

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 8/5. 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
4:30 p.m. - 8:08 p.m.
YSJ
-
ORD
5h 38m
1 stop
Air Canada Logo
8:45 a.m. - 3:40 p.m.
ORD
-
YSJ
4h 55m
1 stop
C$ 707Air Canada
Tue, 5 May - Tue, 12 May
Air Canada Logo
12:20 p.m. - 4:59 p.m.
YSJ
-
ORD
6h 39m
1 stop
Air Canada Logo
2:15 p.m. - 11:52 p.m.
ORD
-
YSJ
7h 37m
1 stop
C$ 719Air Canada
Wed, 10 Jun - Mon, 15 Jun
Air Canada Logo
4:30 p.m. - 8:08 p.m.
YSJ
-
ORD
5h 38m
1 stop
Air Canada Logo
8:20 p.m. - 11:55 a.m.
ORD
-
YSJ
13h 35m
1 stop
C$ 747Air Canada
Fri, 8 May - Fri, 15 May
Air Canada Logo
5:35 a.m. - 9:05 a.m.
YSJ
-
ORD
5h 30m
1 stop
Air Canada Logo
8:20 p.m. - 11:27 a.m.
ORD
-
YSJ
13h 07m
1 stop
C$ 754Air Canada
Wed, 10 Jun - Thu, 11 Jun
United Airlines Logo
4:30 p.m. - 8:08 p.m.
YSJ
-
ORD
5h 38m
1 stop
United Airlines Logo
9:35 p.m. - 3:40 p.m.
ORD
-
YSJ
16h 05m
2 stops
C$ 778United Airlines
Fri, 8 May - Fri, 15 May
United Airlines Logo
4:30 p.m. - 7:46 a.m.
YSJ
-
ORD
17h 16m
2 stops
United Airlines Logo
8:45 a.m. - 3:40 p.m.
ORD
-
YSJ
4h 55m
1 stop
C$ 787United Airlines
Tue, 5 May - Tue, 12 May
United Airlines Logo
4:30 p.m. - 11:26 p.m.
YSJ
-
ORD
8h 56m
2 stops
United Airlines Logo
2:15 p.m. - 11:52 p.m.
ORD
-
YSJ
7h 37m
1 stop
C$ 794United Airlines
Wed, 10 Jun - Mon, 15 Jun
United Airlines Logo
12:20 p.m. - 11:30 p.m.
YSJ
-
ORD
13h 10m
2 stops
United Airlines Logo
2:56 p.m. - 11:52 p.m.
ORD
-
YSJ
6h 56m
1 stop
C$ 799United Airlines
Wed, 10 Jun - Thu, 11 Jun
United Airlines Logo
5:35 a.m. - 4:56 p.m.
YSJ
-
ORD
13h 21m
2 stops
United Airlines Logo
6:00 a.m. - 3:40 p.m.
ORD
-
YSJ
7h 40m
2 stops
C$ 824United Airlines
Tue, 5 May - Tue, 12 May
Multiple Airlines Logo
12:00 p.m. - 9:14 a.m.
YSJ
-
MDW
23h 14m
3 stops
Multiple Airlines Logo
1:49 p.m. - 10:00 a.m.
MDW
-
YSJ
18h 11m
2 stops
C$ 1,326Multiple Airlines
Wed, 10 Jun - Thu, 11 Jun

Air Canada flights from Saint John to Chicago

Our best Air Canada deals on Saint John to Chicago flight tickets
Air Canada
5 May
YSJ4:30 p.m.Saint John
5h 38m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
12 May
ORD8:45 a.m.Chicago O'Hare Intl
4h 55m
1 stop
YSJ3:40 p.m.Saint John
C$ 707
Air Canada
10 Jun
YSJ12:20 p.m.Saint John
6h 39m
1 stop
ORD4:59 p.m.Chicago O'Hare Intl
15 Jun
ORD2:15 p.m.Chicago O'Hare Intl
7h 37m
1 stop
YSJ11:52 p.m.Saint John
C$ 719
Air Canada
8 May
YSJ4:30 p.m.Saint John
5h 38m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
15 May
ORD8:20 p.m.Chicago O'Hare Intl
13h 35m
1 stop
YSJ11:55 a.m.Saint John
C$ 747

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
8 May
YSJ4:30 p.m.Saint John
5h 38m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
15 May
ORD9:35 p.m.Chicago O'Hare Intl
16h 05m
2 stops
YSJ3:40 p.m.Saint John
C$ 778
United Airlines
5 May
YSJ4:30 p.m.Saint John
17h 16m
2 stops
ORD7:46 a.m.Chicago O'Hare Intl
12 May
ORD8:45 a.m.Chicago O'Hare Intl
4h 55m
1 stop
YSJ3:40 p.m.Saint John
C$ 787
United Airlines
10 Jun
YSJ4:30 p.m.Saint John
8h 56m
2 stops
ORD11:26 p.m.Chicago O'Hare Intl
15 Jun
ORD2:15 p.m.Chicago O'Hare Intl
7h 37m
1 stop
YSJ11:52 p.m.Saint John
C$ 794

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 25 March 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
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 5/5

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

1 stop5h 38m

Chicago O'Hare Intl

Tue 12/5

8:45 a.m.-3:40 p.m.

1 stop4h 55m

C$ 707

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 10/6

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

1 stop6h 39m

Chicago O'Hare Intl

Mon 15/6

2:15 p.m.-11:52 p.m.

1 stop7h 37m

C$ 719

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 8/5

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

1 stop5h 38m

Chicago O'Hare Intl

Fri 15/5

8:20 p.m.-11:55 a.m.

1 stop13h 35m

C$ 747

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 10/6

5:35 a.m.-9:05 a.m.

1 stop5h 30m

Chicago O'Hare Intl

Thu 11/6

8:20 p.m.-11:27 a.m.

1 stop13h 07m

C$ 754

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 8/5

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

1 stop5h 38m

Chicago O'Hare Intl

Fri 15/5

9:35 p.m.-3:40 p.m.

2 stops16h 05m

C$ 778

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 5/5

4:30 p.m.-7:46 a.m.

2 stops17h 16m

Chicago O'Hare Intl

Tue 12/5

8:45 a.m.-3:40 p.m.

1 stop4h 55m

C$ 787

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 10/6

4:30 p.m.-11:26 p.m.

2 stops8h 56m

Chicago O'Hare Intl

Mon 15/6

2:15 p.m.-11:52 p.m.

1 stop7h 37m

C$ 794

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 10/6

12:20 p.m.-11:30 p.m.

2 stops13h 10m

Chicago O'Hare Intl

Thu 11/6

2:56 p.m.-11:52 p.m.

1 stop6h 56m

C$ 799

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 5/5

5:35 a.m.-4:56 p.m.

2 stops13h 21m

Chicago O'Hare Intl

Tue 12/5

6:00 a.m.-3:40 p.m.

2 stops7h 40m

C$ 824

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Wed 10/6

12:00 p.m.-9:14 a.m.

3 stops23h 14m

Chicago Midway

Thu 11/6

1:49 p.m.-10:00 a.m.

2 stops18h 11m

C$ 1,326

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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?

United Airlines is the most popular carrier 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 30m

Direct flights

None
The fastest flight from Saint John to Chicago takes 5h 30m
There are no direct flights from Saint John to Chicago. There are no popular flight routes from Saint John to Chicago.
Search flight deals

  • 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 30m.

  • 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
Munster
Hammond

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
Fri 24/4
Fri 1/5
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