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Cheap flights from Saint John to Chicago from C$ 402

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 28/9. 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
11:05 a.m. - 8:21 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
11h 16m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Island
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 906Air Canada
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
11:05 a.m. - 2:52 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 47m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 906Air Canada
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
11:05 a.m. - 2:52 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 47m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 907Air Canada
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
11:05 a.m. - 8:21 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
11h 16m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Island
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 907Air Canada
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
11:05 a.m. - 2:52 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 47m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 910Air Canada
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
11:05 a.m. - 8:21 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
11h 16m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Island
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 910Air Canada
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
11:05 a.m. - 2:52 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 47m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 911Air Canada
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
11:05 a.m. - 8:21 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
11h 16m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Island
Air Canada Logo
10:05 a.m. - 5:19 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Toronto Pearson Intl
C$ 911Air Canada
Sat, 5 Dec - Wed, 9 Dec
Multiple Airlines Logo
5:00 a.m. - 9:48 a.m.YSJ  Saint John-ORD Chicago O'Hare Intl
6h 48m1 stop Toronto Pearson Intl
Multiple Airlines Logo
8:45 a.m. - 3:59 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 14m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 914Multiple Airlines
Wed, 30 Sep - Wed, 7 Oct
Multiple Airlines Logo
10:45 a.m. - 9:40 a.m.YSJ  Saint John-MDW Chicago Midway
24h 55m1 stop Toronto Pearson Intl
Multiple Airlines Logo
3:20 p.m. - 10:00 a.m.MDW  Chicago Midway-YSJ Saint John
16h 40m1 stop Toronto Island
C$ 916Multiple Airlines
Fri, 28 Aug - Tue, 1 Sep

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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
5 Dec
YSJ11:05 a.m.Saint John
11h 16m
2 stops
ORD8:21 p.m.Chicago O'Hare Intl
9 Dec
ORD10:05 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ5:19 p.m.Saint John
C$ 906
Air Canada
5 Dec
YSJ11:05 a.m.Saint John
11h 16m
2 stops
ORD8:21 p.m.Chicago O'Hare Intl
9 Dec
ORD10:05 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ5:19 p.m.Saint John
C$ 907
Air Canada
5 Dec
YSJ11:05 a.m.Saint John
11h 16m
2 stops
ORD8:21 p.m.Chicago O'Hare Intl
9 Dec
ORD10:05 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ5:19 p.m.Saint John
C$ 910

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
30 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
7 Oct
ORD5:00 a.m.Chicago O'Hare Intl
8h 59m
2 stops
YSJ3:59 p.m.Saint John
C$ 1,010
United Airlines
16 Nov
YSJ11:05 a.m.Saint John
5h 47m
1 stop
ORD2:52 p.m.Chicago O'Hare Intl
20 Nov
ORD7:45 p.m.Chicago O'Hare Intl
19h 34m
2 stops
YSJ5:19 p.m.Saint John
C$ 1,015
United Airlines
30 Sep
YSJ4:40 p.m.Saint John
8h 41m
2 stops
ORD11:21 p.m.Chicago O'Hare Intl
7 Oct
ORD5:00 a.m.Chicago O'Hare Intl
8h 59m
2 stops
YSJ3:59 p.m.Saint John
C$ 1,017

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 August 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 Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-8:21 p.m.

2 stops11h 16m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 906
Quickest round-trip

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-2:52 p.m.

1 stop5h 47m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 906

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-2:52 p.m.

1 stop5h 47m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 907

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-8:21 p.m.

2 stops11h 16m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 907

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-2:52 p.m.

1 stop5h 47m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 910

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-8:21 p.m.

2 stops11h 16m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 910

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-2:52 p.m.

1 stop5h 47m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 911

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 5/12

11:05 a.m.-8:21 p.m.

2 stops11h 16m

Chicago O'Hare Intl

Wed 9/12

10:05 a.m.-5:19 p.m.

1 stop5h 14m

C$ 911

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Wed 30/9

5:00 a.m.-9:48 a.m.

1 stop6h 48m

Chicago O'Hare Intl

Wed 7/10

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

1 stop5h 14m

C$ 914

Saint JohnChicago

YSJ Saint John - MDW Chicago Midway

YSJMDW

Saint John

Fri 28/8

10:45 a.m.-9:40 a.m.

1 stop24h 55m

Chicago Midway

Tue 1/9

3:20 p.m.-10:00 a.m.

1 stop16h 40m

C$ 916

Flights are sorted by cheapest round-trip flights first.

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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 47m

Direct flights

None
The fastest flight from Saint John to Chicago takes 5h 47m
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 47m.

  • 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
Valparaiso
Portage

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