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Cheap flights from Saint John to Chicago from C$ 414

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 16/8. 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

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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
5:35 a.m. - 9:00 a.m.
YSJ
-
ORD
5h 25m
1 stop
Air Canada Logo
8:35 a.m. - 3:55 p.m.
ORD
-
YSJ
5h 20m
1 stop
C$ 807Air Canada
Mon, 15 Jun - Sun, 21 Jun
Air Canada Logo
5:40 a.m. - 9:00 a.m.
YSJ
-
ORD
5h 20m
1 stop
Air Canada Logo
8:45 a.m. - 3:56 p.m.
ORD
-
YSJ
5h 11m
1 stop
C$ 808Air Canada
Sun, 28 Jun - Sun, 5 Jul
United Airlines Logo
12:20 p.m. - 11:26 p.m.
YSJ
-
ORD
13h 06m
2 stops
United Airlines Logo
3:45 p.m. - 11:50 p.m.
ORD
-
YSJ
6h 05m
1 stop
C$ 970United Airlines
Mon, 15 Jun - Sun, 21 Jun
United Airlines Logo
12:20 p.m. - 11:26 p.m.
YSJ
-
ORD
13h 06m
2 stops
United Airlines Logo
5:00 a.m. - 3:55 p.m.
ORD
-
YSJ
8h 55m
2 stops
C$ 1,139United Airlines
Mon, 15 Jun - Sun, 21 Jun
United Airlines Logo
12:50 p.m. - 11:31 p.m.
YSJ
-
ORD
12h 41m
2 stops
United Airlines Logo
8:45 a.m. - 3:56 p.m.
ORD
-
YSJ
5h 11m
1 stop
C$ 1,142United Airlines
Sun, 28 Jun - Sun, 5 Jul
United Airlines Logo
12:50 p.m. - 7:42 a.m.
YSJ
-
ORD
20h 52m
2 stops
United Airlines Logo
6:00 a.m. - 3:56 p.m.
ORD
-
YSJ
7h 56m
2 stops
C$ 1,300United Airlines
Sun, 28 Jun - Sun, 5 Jul
Multiple Airlines Logo
6:55 a.m. - 9:40 a.m.
YSJ
-
MDW
28h 45m
2 stops
Multiple Airlines Logo
9:54 a.m. - 10:00 a.m.
MDW
-
YSJ
22h 06m
2 stops
C$ 1,431Multiple Airlines
Sun, 28 Jun - Sun, 5 Jul
Multiple Airlines Logo
10:45 a.m. - 6:31 p.m.
YSJ
-
MDW
33h 46m
3 stops
Multiple Airlines Logo
9:17 a.m. - 10:00 a.m.
MDW
-
YSJ
22h 43m
2 stops
C$ 1,469Multiple Airlines
Mon, 15 Jun - Sun, 21 Jun
Multiple Airlines Logo
6:55 a.m. - 2:35 p.m.
YSJ
-
MDW
33h 40m
3 stops
Multiple Airlines Logo
3:20 p.m. - 11:15 p.m.
MDW
-
YSJ
29h 55m
2 stops
C$ 1,491Multiple Airlines
Sun, 28 Jun - Sun, 5 Jul
Multiple Airlines Logo
6:55 a.m. - 9:14 a.m.
YSJ
-
MDW
28h 19m
3 stops
Multiple Airlines Logo
1:26 p.m. - 11:15 p.m.
MDW
-
YSJ
31h 49m
3 stops
C$ 1,669Multiple Airlines
Sun, 28 Jun - Sun, 5 Jul

Air Canada flights from Saint John to Chicago

Our best Air Canada deals on Saint John to Chicago flight tickets
Air Canada
15 Jun
YSJ5:35 a.m.Saint John
5h 25m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
21 Jun
ORD8:35 a.m.Chicago O'Hare Intl
5h 20m
1 stop
YSJ3:55 p.m.Saint John
C$ 807
Air Canada
28 Jun
YSJ5:40 a.m.Saint John
5h 20m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
5 Jul
ORD8:45 a.m.Chicago O'Hare Intl
5h 11m
1 stop
YSJ3:56 p.m.Saint John
C$ 808

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
15 Jun
YSJ12:20 p.m.Saint John
13h 06m
2 stops
ORD11:26 p.m.Chicago O'Hare Intl
21 Jun
ORD3:45 p.m.Chicago O'Hare Intl
6h 05m
1 stop
YSJ11:50 p.m.Saint John
C$ 970
United Airlines
15 Jun
YSJ12:20 p.m.Saint John
13h 06m
2 stops
ORD11:26 p.m.Chicago O'Hare Intl
21 Jun
ORD5:00 a.m.Chicago O'Hare Intl
8h 55m
2 stops
YSJ3:55 p.m.Saint John
C$ 1,139
United Airlines
28 Jun
YSJ12:50 p.m.Saint John
12h 41m
2 stops
ORD11:31 p.m.Chicago O'Hare Intl
5 Jul
ORD8:45 a.m.Chicago O'Hare Intl
5h 11m
1 stop
YSJ3:56 p.m.Saint John
C$ 1,142

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 18 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 15/6

5:35 a.m.-9:00 a.m.

1 stop5h 25m

Chicago O'Hare Intl

Sun 21/6

8:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 807
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 28/6

5:40 a.m.-9:00 a.m.

1 stop5h 20m

Chicago O'Hare Intl

Sun 5/7

8:45 a.m.-3:56 p.m.

1 stop5h 11m

C$ 808

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 15/6

12:20 p.m.-11:26 p.m.

2 stops13h 06m

Chicago O'Hare Intl

Sun 21/6

3:45 p.m.-11:50 p.m.

1 stop6h 05m

C$ 970

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 15/6

12:20 p.m.-11:26 p.m.

2 stops13h 06m

Chicago O'Hare Intl

Sun 21/6

5:00 a.m.-3:55 p.m.

2 stops8h 55m

C$ 1,139

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 28/6

12:50 p.m.-11:31 p.m.

2 stops12h 41m

Chicago O'Hare Intl

Sun 5/7

8:45 a.m.-3:56 p.m.

1 stop5h 11m

C$ 1,142

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 28/6

12:50 p.m.-7:42 a.m.

2 stops20h 52m

Chicago O'Hare Intl

Sun 5/7

6:00 a.m.-3:56 p.m.

2 stops7h 56m

C$ 1,300

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Sun 28/6

6:55 a.m.-9:40 a.m.

2 stops28h 45m

Chicago Midway

Sun 5/7

9:54 a.m.-10:00 a.m.

2 stops22h 06m

C$ 1,431

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Mon 15/6

10:45 a.m.-6:31 p.m.

3 stops33h 46m

Chicago Midway

Sun 21/6

9:17 a.m.-10:00 a.m.

2 stops22h 43m

C$ 1,469

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Sun 28/6

6:55 a.m.-2:35 p.m.

3 stops33h 40m

Chicago Midway

Sun 5/7

3:20 p.m.-11:15 p.m.

2 stops29h 55m

C$ 1,491

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Sun 28/6

6:55 a.m.-9:14 a.m.

3 stops28h 19m

Chicago Midway

Sun 5/7

1:26 p.m.-11:15 p.m.

3 stops31h 49m

C$ 1,669

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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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 50m

Direct flights

None
The fastest flight from Saint John to Chicago takes 5h 50m
There are no direct flights from Saint John to Chicago. There are no popular flight routes from Saint John to Chicago.
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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 50m.

  • 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.

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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