Cheap flights from Saint John to Chicago from C$ 404

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 5/3. 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.

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
4:15 p.m. - 8:10 p.m.
YSJ
-
ORD
5h 55m
1 stop
Air Canada Logo
4:15 p.m. - 11:52 p.m.
ORD
-
YSJ
5h 37m
1 stop
C$ 740Air Canada
Mon, 23 Mar - Wed, 1 Apr
United Airlines Logo
5:40 a.m. - 9:13 a.m.
YSJ
-
ORD
5h 33m
1 stop
United Airlines Logo
9:18 p.m. - 11:10 a.m.
ORD
-
YSJ
11h 52m
2 stops
C$ 813United Airlines
Mon, 23 Mar - Wed, 1 Apr
United Airlines Logo
4:15 p.m. - 9:50 a.m.
YSJ
-
ORD
19h 35m
2 stops
United Airlines Logo
9:18 p.m. - 11:10 a.m.
ORD
-
YSJ
11h 52m
2 stops
C$ 814United Airlines
Mon, 23 Mar - Wed, 1 Apr
Multiple Airlines Logo
12:00 p.m. - 11:17 p.m.
YSJ
-
ORD
37h 17m
3 stops
Multiple Airlines Logo
9:30 a.m. - 3:45 p.m.
ORD
-
YSJ
28h 15m
3 stops
C$ 1,106Multiple Airlines
Mon, 23 Mar - Wed, 1 Apr
Multiple Airlines Logo
12:00 p.m. - 12:35 p.m.
YSJ
-
ORD
26h 35m
2 stops
Multiple Airlines Logo
9:30 a.m. - 3:45 p.m.
ORD
-
YSJ
28h 15m
3 stops
C$ 1,143Multiple Airlines
Mon, 23 Mar - Wed, 1 Apr

Air Canada flights from Saint John to Chicago

Our best Air Canada deals on Saint John to Chicago flight tickets
Air Canada
23 Mar
YSJ4:15 p.m.Saint John
5h 55m
1 stop
ORD8:10 p.m.Chicago O'Hare Intl
1 Apr
ORD4:15 p.m.Chicago O'Hare Intl
5h 37m
1 stop
YSJ11:52 p.m.Saint John
C$ 740
Air Canada
29 May
YSJ4:30 p.m.Saint John
5h 38m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
1 Jun
ORD2:15 p.m.Chicago O'Hare Intl
7h 37m
1 stop
YSJ11:52 p.m.Saint John
C$ 742
Air Canada
29 May
YSJ4:30 p.m.Saint John
18h 30m
2 stops
ORD9:00 a.m.Chicago O'Hare Intl
1 Jun
ORD2:15 p.m.Chicago O'Hare Intl
7h 37m
1 stop
YSJ11:52 p.m.Saint John
C$ 802

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
23 Mar
YSJ5:40 a.m.Saint John
5h 33m
1 stop
ORD9:13 a.m.Chicago O'Hare Intl
1 Apr
ORD9:18 p.m.Chicago O'Hare Intl
11h 52m
2 stops
YSJ11:10 a.m.Saint John
C$ 813
United Airlines
23 Mar
YSJ4:15 p.m.Saint John
19h 35m
2 stops
ORD9:50 a.m.Chicago O'Hare Intl
1 Apr
ORD9:18 p.m.Chicago O'Hare Intl
11h 52m
2 stops
YSJ11:10 a.m.Saint John
C$ 814

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 21 January 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

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 23/3

4:15 p.m.-8:10 p.m.

1 stop5h 55m

Chicago O'Hare Intl

Wed 1/4

4:15 p.m.-11:52 p.m.

1 stop5h 37m

C$ 740

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 23/3

5:40 a.m.-9:13 a.m.

1 stop5h 33m

Chicago O'Hare Intl

Wed 1/4

9:18 p.m.-11:10 a.m.

2 stops11h 52m

C$ 813

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 23/3

4:15 p.m.-9:50 a.m.

2 stops19h 35m

Chicago O'Hare Intl

Wed 1/4

9:18 p.m.-11:10 a.m.

2 stops11h 52m

C$ 814

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 23/3

12:00 p.m.-11:17 p.m.

3 stops37h 17m

Chicago O'Hare Intl

Wed 1/4

9:30 a.m.-3:45 p.m.

3 stops28h 15m

C$ 1,106

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 23/3

12:00 p.m.-12:35 p.m.

2 stops26h 35m

Chicago O'Hare Intl

Wed 1/4

9:30 a.m.-3:45 p.m.

3 stops28h 15m

C$ 1,143

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 5/3

4:15 p.m.-8:10 p.m.

1 stop5h 55m

C$ 404

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 5/3

4:15 p.m.-11:44 p.m.

2 stops9h 29m

C$ 448

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 5/3

5:40 a.m.-5:01 p.m.

3 stops13h 21m

C$ 1,240

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 38m

Direct flights

None
The fastest flight from Saint John to Chicago takes 5h 38m
There are no direct flights from Saint John to Chicago. There are no popular flight routes 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 38m.

  • 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
Munster
Hammond
Merrillville

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 20/2
Fri 27/2

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