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Cheap flights from Saint John to Chicago from $301

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 6/7. 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
0 bags

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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
4:30 pm - 8:05 pm
YSJ
-
ORD
5h 35m
1 stop
Air Canada Logo
8:45 am - 3:50 pm
ORD
-
YSJ
5h 05m
1 stop
$528Air Canada
Tue, Sep 1 - Mon, Sep 7
Air Canada Logo
4:30 pm - 8:08 pm
YSJ
-
ORD
5h 38m
1 stop
Air Canada Logo
8:45 am - 3:40 pm
ORD
-
YSJ
4h 55m
1 stop
$539Air Canada
Fri, May 22 - Thu, May 28
United Airlines Logo
4:30 pm - 7:44 am
YSJ
-
ORD
17h 14m
2 stops
United Airlines Logo
8:45 am - 3:50 pm
ORD
-
YSJ
5h 05m
1 stop
$591United Airlines
Tue, Sep 1 - Mon, Sep 7
United Airlines Logo
5:40 am - 9:00 am
YSJ
-
ORD
5h 20m
1 stop
United Airlines Logo
2:56 pm - 11:50 pm
ORD
-
YSJ
6h 54m
1 stop
$614United Airlines
Thu, Jun 25 - Thu, Jul 2
Air Canada Logo
5:00 am - 12:11 pm
YSJ
-
ORD
9h 11m
2 stops
Air Canada Logo
8:45 am - 3:40 pm
ORD
-
YSJ
4h 55m
1 stop
$628Air Canada
Fri, May 22 - Thu, May 28
United Airlines Logo
5:40 am - 9:45 am
YSJ
-
ORD
6h 05m
1 stop
United Airlines Logo
7:10 am - 11:50 pm
ORD
-
YSJ
14h 40m
2 stops
$642United Airlines
Thu, Jun 25 - Thu, Jul 2
United Airlines Logo
12:50 pm - 10:06 pm
YSJ
-
ORD
11h 16m
2 stops
United Airlines Logo
11:07 am - 11:50 pm
ORD
-
YSJ
10h 43m
2 stops
$758United Airlines
Thu, Jun 25 - Thu, Jul 2
United Airlines Logo
5:00 am - 2:30 pm
YSJ
-
ORD
11h 30m
2 stops
United Airlines Logo
7:00 am - 1:25 am
ORD
-
YSJ
16h 25m
2 stops
$855United Airlines
Tue, Sep 1 - Mon, Sep 7
Multiple Airlines Logo
11:30 am - 2:35 pm
YSJ
-
ORD
29h 05m
2 stops
Multiple Airlines Logo
5:30 pm - 11:15 pm
ORD
-
YSJ
27h 45m
3 stops
$946Multiple Airlines
Tue, Sep 1 - Mon, Sep 7
Multiple Airlines Logo
11:30 am - 9:35 pm
YSJ
-
ORD
12h 05m
3 stops
Multiple Airlines Logo
5:30 pm - 11:15 pm
ORD
-
YSJ
27h 45m
3 stops
$1,008Multiple Airlines
Tue, Sep 1 - Mon, Sep 7

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
Sep 1
YSJ4:30 pmSaint John
5h 35m
1 stop
ORD8:05 pmChicago O'Hare Intl
Sep 7
ORD8:45 amChicago O'Hare Intl
5h 05m
1 stop
YSJ3:50 pmSaint John
$528
Air Canada
May 22
YSJ4:30 pmSaint John
5h 38m
1 stop
ORD8:08 pmChicago O'Hare Intl
May 28
ORD8:45 amChicago O'Hare Intl
4h 55m
1 stop
YSJ3:40 pmSaint John
$539
Air Canada
May 22
YSJ5:00 amSaint John
9h 11m
2 stops
ORD12:11 pmChicago O'Hare Intl
May 28
ORD8:45 amChicago O'Hare Intl
4h 55m
1 stop
YSJ3:40 pmSaint John
$628

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
Sep 1
YSJ4:30 pmSaint John
17h 14m
2 stops
ORD7:44 amChicago O'Hare Intl
Sep 7
ORD8:45 amChicago O'Hare Intl
5h 05m
1 stop
YSJ3:50 pmSaint John
$591
United Airlines
Jun 25
YSJ5:40 amSaint John
5h 20m
1 stop
ORD9:00 amChicago O'Hare Intl
Jul 2
ORD2:56 pmChicago O'Hare Intl
6h 54m
1 stop
YSJ11:50 pmSaint John
$614
United Airlines
Jun 25
YSJ5:40 amSaint John
6h 05m
1 stop
ORD9:45 amChicago O'Hare Intl
Jul 2
ORD7:10 amChicago O'Hare Intl
14h 40m
2 stops
YSJ11:50 pmSaint John
$642

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 May 11, 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

Tue 9/1

4:30 pm-8:05 pm

1 stop5h 35m

Chicago O'Hare Intl

Mon 9/7

8:45 am-3:50 pm

1 stop5h 05m

$528
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 5/22

4:30 pm-8:08 pm

1 stop5h 38m

Chicago O'Hare Intl

Thu 5/28

8:45 am-3:40 pm

1 stop4h 55m

$539

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 9/1

4:30 pm-7:44 am

2 stops17h 14m

Chicago O'Hare Intl

Mon 9/7

8:45 am-3:50 pm

1 stop5h 05m

$591

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 6/25

5:40 am-9:00 am

1 stop5h 20m

Chicago O'Hare Intl

Thu 7/2

2:56 pm-11:50 pm

1 stop6h 54m

$614

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 5/22

5:00 am-12:11 pm

2 stops9h 11m

Chicago O'Hare Intl

Thu 5/28

8:45 am-3:40 pm

1 stop4h 55m

$628

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 6/25

5:40 am-9:45 am

1 stop6h 05m

Chicago O'Hare Intl

Thu 7/2

7:10 am-11:50 pm

2 stops14h 40m

$642

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Thu 6/25

12:50 pm-10:06 pm

2 stops11h 16m

Chicago O'Hare Intl

Thu 7/2

11:07 am-11:50 pm

2 stops10h 43m

$758

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 9/1

5:00 am-2:30 pm

2 stops11h 30m

Chicago O'Hare Intl

Mon 9/7

7:00 am-1:25 am

2 stops16h 25m

$855

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 9/1

11:30 am-2:35 pm

2 stops29h 05m

Chicago O'Hare Intl

Mon 9/7

5:30 pm-11:15 pm

3 stops27h 45m

$946

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Tue 9/1

11:30 am-9:35 pm

3 stops12h 05m

Chicago O'Hare Intl

Mon 9/7

5:30 pm-11:15 pm

3 stops27h 45m

$1,008

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 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?

United Airlines is the most popular carrier 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 20m

Direct flights

None
The fastest flight from Saint John to Chicago O'Hare Intl Airport takes 5h 20m
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 20m, 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
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Elgin
Tinley Park

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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