Cheap flights from Saint John to Chicago from C$ 337

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 23/10. 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 (YSJ-CHI)

Cheap round-trip flights

Air Canada Logo
11:35 a.m. - 2:48 p.m.YSJ-ORD
5h 13m1 stop
Air Canada Logo
10:00 a.m. - 5:14 p.m.ORD-YSJ
5h 14m1 stop
C$ 583Air Canada
Find Deal
Wed, 22 Oct - Wed, 29 Oct
United Airlines Logo
11:35 a.m. - 2:48 p.m.YSJ-ORD
5h 13m1 stop
United Airlines Logo
9:05 p.m. - 11:15 a.m.ORD-YSJ
12h 10m2 stops
C$ 673United Airlines
Find Deal
Wed, 22 Oct - Wed, 29 Oct
United Airlines Logo
11:35 a.m. - 9:16 p.m.YSJ-ORD
11h 41m2 stops
United Airlines Logo
9:05 p.m. - 11:15 a.m.ORD-YSJ
12h 10m2 stops
C$ 681United Airlines
Find Deal
Wed, 22 Oct - Wed, 29 Oct
 Logo
12:00 p.m. - 8:39 a.m.YSJ-MDW
22h 39m3 stops
 Logo
9:20 a.m. - 3:45 p.m.MDW-YSJ
28h 25m3 stops
C$ 880
Find Deal
Wed, 22 Oct - Wed, 29 Oct
 Logo
4:15 p.m. - 4:24 p.m.YSJ-MDW
26h 09m2 stops
 Logo
9:20 a.m. - 3:45 p.m.MDW-YSJ
28h 25m3 stops
C$ 1,093
Find Deal
Wed, 22 Oct - Wed, 29 Oct

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
22 Oct
YSJ11:35 a.m.Saint John
5h 13m
1 stop
ORD2:48 p.m.Chicago O'Hare Intl
29 Oct
ORD9:05 p.m.Chicago O'Hare Intl
12h 10m
2 stops
YSJ11:15 a.m.Saint John
United Airlines
22 Oct
YSJ11:35 a.m.Saint John
11h 41m
2 stops
ORD9:16 p.m.Chicago O'Hare Intl
29 Oct
ORD9:05 p.m.Chicago O'Hare Intl
12h 10m
2 stops
YSJ11:15 a.m.Saint John

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 9 September 2025.
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

Wed 22/10

11:35 a.m.-2:48 p.m.

1 stop5h 13m

Chicago O'Hare Intl

Wed 29/10

10:00 a.m.-5:14 p.m.

1 stop5h 14m

C$ 583

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 22/10

11:35 a.m.-2:48 p.m.

1 stop5h 13m

Chicago O'Hare Intl

Wed 29/10

9:05 p.m.-11:15 a.m.

2 stops12h 10m

C$ 673

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 22/10

11:35 a.m.-9:16 p.m.

2 stops11h 41m

Chicago O'Hare Intl

Wed 29/10

9:05 p.m.-11:15 a.m.

2 stops12h 10m

C$ 681

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Wed 22/10

12:00 p.m.-8:39 a.m.

3 stops22h 39m

Chicago Midway

Wed 29/10

9:20 a.m.-3:45 p.m.

3 stops28h 25m

C$ 880

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Wed 22/10

4:15 p.m.-4:24 p.m.

2 stops26h 09m

Chicago Midway

Wed 29/10

9:20 a.m.-3:45 p.m.

3 stops28h 25m

C$ 1,093

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 23/10

5:55 a.m.-9:09 a.m.

1 stop5h 14m

C$ 337

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 23/10

5:55 a.m.-7:58 p.m.

2 stops16h 03m

C$ 392

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Thu 23/10

12:00 p.m.-4:24 p.m.

3 stops30h 24m

C$ 403

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Thu 23/10

12:00 p.m.-4:24 p.m.

2 stops30h 24m

C$ 409

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 23/10

12:00 p.m.-11:44 p.m.

3 stops37h 44m

C$ 452

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

Direct flights

None
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 13m.

  • 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.

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1 adult
Thu 9/10
Thu 16/10

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