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Cheap flights from Saint John to Chicago from $312

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 8/9. 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
4:40 pm - 8:12 pm
YSJ
-
ORD
5h 32m
1 stop
Air Canada Logo
8:45 am - 3:59 pm
ORD
-
YSJ
5h 14m
1 stop
$538Air Canada
Mon, Oct 19 - Wed, Oct 21
Air Canada Logo
11:05 am - 8:21 pm
YSJ
-
ORD
11h 16m
2 stops
Air Canada Logo
4:30 pm - 11:24 pm
ORD
-
YSJ
4h 54m
1 stop
$541Air Canada
Mon, Dec 7 - Wed, Dec 9
Air Canada Logo
11:05 am - 8:21 pm
YSJ
-
ORD
11h 16m
2 stops
Air Canada Logo
4:30 pm - 11:24 pm
ORD
-
YSJ
4h 54m
1 stop
$542Air Canada
Mon, Dec 7 - Wed, Dec 9
Air Canada Logo
11:05 am - 8:21 pm
YSJ
-
ORD
11h 16m
2 stops
Air Canada Logo
4:30 pm - 11:24 pm
ORD
-
YSJ
4h 54m
1 stop
$543Air Canada
Mon, Dec 7 - Wed, Dec 9
United Airlines Logo
4:40 pm - 8:12 pm
YSJ
-
ORD
5h 32m
1 stop
United Airlines Logo
5:00 am - 3:59 pm
ORD
-
YSJ
8h 59m
2 stops
$597United Airlines
Mon, Oct 19 - Wed, Oct 21
Air Canada Logo
11:05 am - 8:21 pm
YSJ
-
ORD
11h 16m
2 stops
Air Canada Logo
11:45 am - 11:24 pm
ORD
-
YSJ
9h 39m
2 stops
$600Air Canada
Mon, Dec 7 - Wed, Dec 9
Air Canada Logo
11:05 am - 8:21 pm
YSJ
-
ORD
11h 16m
2 stops
Air Canada Logo
2:00 pm - 11:24 pm
ORD
-
YSJ
7h 24m
2 stops
$601Air Canada
Mon, Dec 7 - Wed, Dec 9
Air Canada Logo
4:40 pm - 8:05 pm
YSJ
-
ORD
5h 25m
1 stop
Air Canada Logo
8:40 am - 4:00 pm
ORD
-
YSJ
5h 20m
1 stop
$602Air Canada
Fri, Aug 7 - Fri, Aug 14
United Airlines Logo
4:40 pm - 11:21 pm
YSJ
-
ORD
8h 41m
2 stops
United Airlines Logo
6:00 am - 3:59 pm
ORD
-
YSJ
7h 59m
2 stops
$603United Airlines
Mon, Oct 19 - Wed, Oct 21
Air Canada Logo
11:05 am - 8:21 pm
YSJ
-
ORD
11h 16m
2 stops
Air Canada Logo
4:30 pm - 11:24 pm
ORD
-
YSJ
4h 54m
1 stop
$614Air Canada
Mon, Dec 7 - Wed, Dec 9

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United Airlines flights from Saint John to Chicago O'Hare Intl Airport

Our best United Airlines deals on Saint John to Chicago O'Hare Intl Airport flight tickets
United Airlines
Oct 19
YSJ4:40 pmSaint John
5h 32m
1 stop
ORD8:12 pmChicago O'Hare Intl
Oct 21
ORD5:00 amChicago O'Hare Intl
8h 59m
2 stops
YSJ3:59 pmSaint John
$597
United Airlines
Oct 19
YSJ4:40 pmSaint John
8h 41m
2 stops
ORD11:21 pmChicago O'Hare Intl
Oct 21
ORD6:00 amChicago O'Hare Intl
7h 59m
2 stops
YSJ3:59 pmSaint John
$603
United Airlines
Aug 7
YSJ4:40 pmSaint John
5h 25m
1 stop
ORD8:05 pmChicago O'Hare Intl
Aug 14
ORD11:15 amChicago O'Hare Intl
11h 40m
2 stops
YSJ12:55 amSaint John
$666

Air Canada flights from Saint John to Chicago O'Hare Intl Airport

Our best Air Canada deals on Saint John to Chicago O'Hare Intl Airport flight tickets
Air Canada
Oct 19
YSJ4:40 pmSaint John
5h 32m
1 stop
ORD8:12 pmChicago O'Hare Intl
Oct 21
ORD8:45 amChicago O'Hare Intl
5h 14m
1 stop
YSJ3:59 pmSaint John
$538
Air Canada
Dec 7
YSJ11:05 amSaint John
11h 16m
2 stops
ORD8:21 pmChicago O'Hare Intl
Dec 9
ORD4:30 pmChicago O'Hare Intl
4h 54m
1 stop
YSJ11:24 pmSaint John
$541
Air Canada
Dec 7
YSJ11:05 amSaint John
5h 47m
1 stop
ORD2:52 pmChicago O'Hare Intl
Dec 9
ORD4:30 pmChicago O'Hare Intl
4h 54m
1 stop
YSJ11:24 pmSaint John
$542

momondo Fare Finder

 
Customize your flight search to find flights from Saint John to Chicago O'Hare Intl Airport 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 832,500 searches. Data last updated June 28, 2026.
Use the filters below to find and compare flights from Saint John to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 10/19

4:40 pm-8:12 pm

1 stop5h 32m

Chicago O'Hare Intl

Wed 10/21

8:45 am-3:59 pm

1 stop5h 14m

$538

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 12/7

11:05 am-8:21 pm

2 stops11h 16m

Chicago O'Hare Intl

Wed 12/9

4:30 pm-11:24 pm

1 stop4h 54m

$541

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 12/7

11:05 am-8:21 pm

2 stops11h 16m

Chicago O'Hare Intl

Wed 12/9

4:30 pm-11:24 pm

1 stop4h 54m

$542

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 12/7

11:05 am-8:21 pm

2 stops11h 16m

Chicago O'Hare Intl

Wed 12/9

4:30 pm-11:24 pm

1 stop4h 54m

$543

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 10/19

4:40 pm-8:12 pm

1 stop5h 32m

Chicago O'Hare Intl

Wed 10/21

5:00 am-3:59 pm

2 stops8h 59m

$597

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 12/7

11:05 am-8:21 pm

2 stops11h 16m

Chicago O'Hare Intl

Wed 12/9

11:45 am-11:24 pm

2 stops9h 39m

$600

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 12/7

11:05 am-8:21 pm

2 stops11h 16m

Chicago O'Hare Intl

Wed 12/9

2:00 pm-11:24 pm

2 stops7h 24m

$601
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 8/7

4:40 pm-8:05 pm

1 stop5h 25m

Chicago O'Hare Intl

Fri 8/14

8:40 am-4:00 pm

1 stop5h 20m

$602

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 10/19

4:40 pm-11:21 pm

2 stops8h 41m

Chicago O'Hare Intl

Wed 10/21

6:00 am-3:59 pm

2 stops7h 59m

$603

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 12/7

11:05 am-8:21 pm

2 stops11h 16m

Chicago O'Hare Intl

Wed 12/9

4:30 pm-11:24 pm

1 stop4h 54m

$614

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 O'Hare Intl Airport

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 O'Hare Intl?

Air Canada and United Airlines are the most popular carriers operating from Saint John to Chicago O'Hare Intl

When to book flights from Saint John to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Saint John to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Saint John to Chicago O'Hare Intl Airport (YSJ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Saint John to Chicago O'Hare Intl Airport

Fastest flight time

5h 25m

Direct flights

None
The fastest flight from Saint John to Chicago O'Hare Intl Airport takes 5h 25m
There are no direct flights from Saint John to Chicago O'Hare Intl Airport. There are no popular flight routes from Saint John to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Saint John to Chicago O'Hare Intl Airport

  • How far is Saint John to Chicago O'Hare Intl by plane?

    There are 1111.2 mi between Saint John and Chicago O'Hare Intl. Flights usually cover this in 5h 25m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Saint John Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Saint John Airport to Chicago O'Hare Intl Airport were last updated today.

  • How old do you have to be to fly from Saint John Airport to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Saint John to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Saint John to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Saint John to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Saint John with this policy.

How can momondo help me find flights from Saint John to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Saint John.

I’m not ready to book a flight from Saint John to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Saint John and alert you when they change.

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