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Cheap flights from Saint John to Chicago from C$ 435

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 5/8. 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
1 adult, Economy, 0 bags

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
4:40 p.m. - 8:12 p.m.
YSJ
-
ORD
5h 32m
1 stop
Air Canada Logo
8:45 a.m. - 3:59 p.m.
ORD
-
YSJ
5h 14m
1 stop
C$ 751Air Canada
Tue, 15 Sep - Sat, 19 Sep
Air Canada Logo
4:40 p.m. - 8:12 p.m.
YSJ
-
ORD
5h 32m
1 stop
Air Canada Logo
8:45 a.m. - 3:59 p.m.
ORD
-
YSJ
5h 14m
1 stop
C$ 752Air Canada
Tue, 15 Sep - Sat, 19 Sep
Air Canada Logo
11:05 a.m. - 2:55 p.m.
YSJ
-
ORD
5h 50m
1 stop
Air Canada Logo
4:00 p.m. - 11:54 p.m.
ORD
-
YSJ
5h 54m
1 stop
C$ 759Air Canada
Wed, 2 Dec - Fri, 4 Dec
Air Canada Logo
4:40 p.m. - 8:05 p.m.
YSJ
-
ORD
5h 25m
1 stop
Air Canada Logo
8:45 a.m. - 4:00 p.m.
ORD
-
YSJ
5h 15m
1 stop
C$ 792Air Canada
Fri, 31 Jul - Fri, 7 Aug
United Airlines Logo
4:40 p.m. - 8:12 p.m.
YSJ
-
ORD
5h 32m
1 stop
United Airlines Logo
5:00 a.m. - 3:59 p.m.
ORD
-
YSJ
8h 59m
2 stops
C$ 834United Airlines
Tue, 15 Sep - Sat, 19 Sep
United Airlines Logo
4:40 p.m. - 8:12 p.m.
YSJ
-
ORD
5h 32m
1 stop
United Airlines Logo
5:00 a.m. - 3:59 p.m.
ORD
-
YSJ
8h 59m
2 stops
C$ 836United Airlines
Tue, 15 Sep - Sat, 19 Sep
Air Canada Logo
4:40 p.m. - 12:28 a.m.
YSJ
-
ORD
9h 48m
2 stops
Air Canada Logo
5:00 a.m. - 3:59 p.m.
ORD
-
YSJ
8h 59m
2 stops
C$ 843Air Canada
Tue, 15 Sep - Sat, 19 Sep
United Airlines Logo
4:40 p.m. - 12:28 a.m.
YSJ
-
ORD
9h 48m
2 stops
United Airlines Logo
12:16 p.m. - 11:51 p.m.
ORD
-
YSJ
9h 35m
2 stops
C$ 850United Airlines
Tue, 15 Sep - Sat, 19 Sep
United Airlines Logo
4:40 p.m. - 8:05 p.m.
YSJ
-
ORD
5h 25m
1 stop
United Airlines Logo
8:07 p.m. - 4:00 p.m.
ORD
-
YSJ
17h 53m
2 stops
C$ 936United Airlines
Fri, 31 Jul - Fri, 7 Aug
Multiple Airlines Logo
10:45 a.m. - 5:52 p.m.
YSJ
-
MDW
33h 07m
3 stops
Multiple Airlines Logo
9:59 a.m. - 11:15 p.m.
MDW
-
YSJ
35h 16m
3 stops
C$ 1,416Multiple Airlines
Fri, 31 Jul - Fri, 7 Aug

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Air Canada flights from Saint John to Chicago

Our best Air Canada deals on Saint John to Chicago flight tickets
Air Canada
15 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
19 Sep
ORD8:45 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ3:59 p.m.Saint John
C$ 751
Air Canada
15 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
19 Sep
ORD8:45 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ3:59 p.m.Saint John
C$ 752
Air Canada
2 Dec
YSJ11:05 a.m.Saint John
5h 50m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
4 Dec
ORD4:00 p.m.Chicago O'Hare Intl
5h 54m
1 stop
YSJ11:54 p.m.Saint John
C$ 759

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
15 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
19 Sep
ORD5:00 a.m.Chicago O'Hare Intl
8h 59m
2 stops
YSJ3:59 p.m.Saint John
C$ 834
United Airlines
15 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
19 Sep
ORD5:00 a.m.Chicago O'Hare Intl
8h 59m
2 stops
YSJ3:59 p.m.Saint John
C$ 836
United Airlines
15 Sep
YSJ4:40 p.m.Saint John
9h 48m
2 stops
ORD12:28 a.m.Chicago O'Hare Intl
19 Sep
ORD12:16 p.m.Chicago O'Hare Intl
9h 35m
2 stops
YSJ11:51 p.m.Saint John
C$ 850

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 16 June 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

Tue 15/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Sat 19/9

8:45 a.m.-3:59 p.m.

1 stop5h 14m

C$ 751

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 15/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Sat 19/9

8:45 a.m.-3:59 p.m.

1 stop5h 14m

C$ 752

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 2/12

11:05 a.m.-2:55 p.m.

1 stop5h 50m

Chicago O'Hare Intl

Fri 4/12

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

1 stop5h 54m

C$ 759
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 31/7

4:40 p.m.-8:05 p.m.

1 stop5h 25m

Chicago O'Hare Intl

Fri 7/8

8:45 a.m.-4:00 p.m.

1 stop5h 15m

C$ 792

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 15/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Sat 19/9

5:00 a.m.-3:59 p.m.

2 stops8h 59m

C$ 834

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 15/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Sat 19/9

5:00 a.m.-3:59 p.m.

2 stops8h 59m

C$ 836

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 15/9

4:40 p.m.-12:28 a.m.

2 stops9h 48m

Chicago O'Hare Intl

Sat 19/9

5:00 a.m.-3:59 p.m.

2 stops8h 59m

C$ 843

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 15/9

4:40 p.m.-12:28 a.m.

2 stops9h 48m

Chicago O'Hare Intl

Sat 19/9

12:16 p.m.-11:51 p.m.

2 stops9h 35m

C$ 850

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 31/7

4:40 p.m.-8:05 p.m.

1 stop5h 25m

Chicago O'Hare Intl

Fri 7/8

8:07 p.m.-4:00 p.m.

2 stops17h 53m

C$ 936

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Fri 31/7

10:45 a.m.-5:52 p.m.

3 stops33h 07m

Chicago Midway

Fri 7/8

9:59 a.m.-11:15 p.m.

3 stops35h 16m

C$ 1,416

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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?

United Airlines and Air Canada 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 32m

Direct flights

None
The fastest flight from Saint John to Chicago takes 5h 32m
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 32m.

  • 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