Latest deals
When to book
FAQs
Price Alerts

Cheap flights from Saint John to Chicago from C$ 598

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Saint John to Chicago departing on 14/9. 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.
Multiple Airlines Logo
10:45 a.m. - 11:00 a.m.
YSJ
-
MDW
26h 15m
1 stop
Multiple Airlines Logo
11:45 a.m. - 10:00 a.m.
MDW
-
YSJ
20h 15m
1 stop
C$ 598Multiple Airlines
Mon, 14 Sep - Sun, 20 Sep
Multiple Airlines Logo
10:45 a.m. - 8:41 p.m.
YSJ
-
ORD
11h 56m
1 stop
Multiple Airlines Logo
3:40 p.m. - 10:00 a.m.
ORD
-
YSJ
16h 20m
2 stops
C$ 608Multiple Airlines
Mon, 14 Sep - Sun, 20 Sep
Multiple Airlines Logo
10:45 a.m. - 8:41 p.m.
YSJ
-
ORD
11h 56m
1 stop
Multiple Airlines Logo
5:35 p.m. - 10:00 a.m.
ORD
-
YSJ
14h 25m
1 stop
C$ 659Multiple Airlines
Mon, 14 Sep - Sun, 20 Sep
Multiple Airlines Logo
10:45 a.m. - 4:58 p.m.
YSJ
-
ORD
8h 13m
1 stop
Multiple Airlines Logo
5:35 p.m. - 3:59 p.m.
ORD
-
YSJ
20h 24m
3 stops
C$ 663Multiple Airlines
Mon, 14 Sep - Sun, 20 Sep
Air Canada Logo
4:40 p.m. - 8:05 p.m.
YSJ
-
ORD
5h 25m
1 stop
Air Canada Logo
8:40 a.m. - 4:00 p.m.
ORD
-
YSJ
5h 20m
1 stop
C$ 779Air Canada
Wed, 26 Aug - Sat, 29 Aug
Air Canada Logo
4:40 p.m. - 8:05 p.m.
YSJ
-
ORD
5h 25m
1 stop
Air Canada Logo
8:40 a.m. - 4:00 p.m.
ORD
-
YSJ
5h 20m
1 stop
C$ 789Air Canada
Fri, 28 Aug - Mon, 31 Aug
Air Canada Logo
4:40 p.m. - 9:00 a.m.
YSJ
-
ORD
18h 20m
2 stops
Air Canada Logo
5:35 p.m. - 3:59 p.m.
ORD
-
YSJ
20h 24m
3 stops
C$ 796Air Canada
Mon, 14 Sep - Sun, 20 Sep
Air Canada Logo
5:00 a.m. - 9:00 a.m.
YSJ
-
ORD
6h 00m
1 stop
Air Canada Logo
8:40 a.m. - 4:00 p.m.
ORD
-
YSJ
5h 20m
1 stop
C$ 811Air Canada
Sun, 23 Aug - Sun, 30 Aug
Air Canada Logo
5:00 a.m. - 9:00 a.m.
YSJ
-
ORD
6h 00m
1 stop
Air Canada Logo
8:40 a.m. - 4:00 p.m.
ORD
-
YSJ
5h 20m
1 stop
C$ 813Air Canada
Sun, 23 Aug - Sun, 30 Aug
Multiple Airlines Logo
6:55 a.m. - 2:35 p.m.
YSJ
-
MDW
9h 40m
2 stops
Multiple Airlines Logo
11:45 a.m. - 10:00 a.m.
MDW
-
YSJ
20h 15m
1 stop
C$ 848Multiple Airlines
Mon, 14 Sep - Sun, 20 Sep

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Air Canada flights from Saint John to Chicago

Our best Air Canada deals on Saint John to Chicago flight tickets
Air Canada
26 Aug
YSJ4:40 p.m.Saint John
5h 25m
1 stop
ORD8:05 p.m.Chicago O'Hare Intl
29 Aug
ORD8:40 a.m.Chicago O'Hare Intl
5h 20m
1 stop
YSJ4:00 p.m.Saint John
C$ 779
Air Canada
28 Aug
YSJ4:40 p.m.Saint John
5h 25m
1 stop
ORD8:05 p.m.Chicago O'Hare Intl
31 Aug
ORD8:40 a.m.Chicago O'Hare Intl
5h 20m
1 stop
YSJ4:00 p.m.Saint John
C$ 789
Air Canada
14 Sep
YSJ4:40 p.m.Saint John
18h 20m
2 stops
ORD9:00 a.m.Chicago O'Hare Intl
20 Sep
ORD5:35 p.m.Chicago O'Hare Intl
20h 24m
3 stops
YSJ3:59 p.m.Saint John
C$ 796

United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
26 Aug
YSJ12:50 p.m.Saint John
9h 40m
2 stops
ORD8:30 p.m.Chicago O'Hare Intl
29 Aug
ORD5:00 a.m.Chicago O'Hare Intl
9h 00m
2 stops
YSJ4:00 p.m.Saint John
C$ 1,014
United Airlines
28 Aug
YSJ5:00 a.m.Saint John
7h 47m
2 stops
ORD10:47 a.m.Chicago O'Hare Intl
31 Aug
ORD6:00 a.m.Chicago O'Hare Intl
8h 00m
2 stops
YSJ4:00 p.m.Saint John
C$ 1,024
United Airlines
13 Sep
YSJ5:00 a.m.Saint John
6h 53m
1 stop
ORD9:53 a.m.Chicago O'Hare Intl
20 Sep
ORD6:00 a.m.Chicago O'Hare Intl
7h 59m
2 stops
YSJ3:59 p.m.Saint John
C$ 1,028

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 30 July 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 - MDW

YSJMDW

Saint John

Mon 14/9

10:45 a.m.-11:00 a.m.

1 stop26h 15m

Chicago Midway

Sun 20/9

11:45 a.m.-10:00 a.m.

1 stop20h 15m

C$ 598

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 14/9

10:45 a.m.-8:41 p.m.

1 stop11h 56m

Chicago O'Hare Intl

Sun 20/9

3:40 p.m.-10:00 a.m.

2 stops16h 20m

C$ 608

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 14/9

10:45 a.m.-8:41 p.m.

1 stop11h 56m

Chicago O'Hare Intl

Sun 20/9

5:35 p.m.-10:00 a.m.

1 stop14h 25m

C$ 659

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 14/9

10:45 a.m.-4:58 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Sun 20/9

5:35 p.m.-3:59 p.m.

3 stops20h 24m

C$ 663
Quickest round-trip

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Wed 26/8

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

1 stop5h 25m

Chicago O'Hare Intl

Sat 29/8

8:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 779

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Fri 28/8

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

1 stop5h 25m

Chicago O'Hare Intl

Mon 31/8

8:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 789

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Mon 14/9

4:40 p.m.-9:00 a.m.

2 stops18h 20m

Chicago O'Hare Intl

Sun 20/9

5:35 p.m.-3:59 p.m.

3 stops20h 24m

C$ 796

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 23/8

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

1 stop6h 00m

Chicago O'Hare Intl

Sun 30/8

8:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 811

Saint JohnChicago

YSJ - ORD

YSJORD

Saint John

Sun 23/8

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

1 stop6h 00m

Chicago O'Hare Intl

Sun 30/8

8:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 813

Saint JohnChicago

YSJ - MDW

YSJMDW

Saint John

Mon 14/9

6:55 a.m.-2:35 p.m.

2 stops9h 40m

Chicago Midway

Sun 20/9

11:45 a.m.-10:00 a.m.

1 stop20h 15m

C$ 848

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 25m

Direct flights

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

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 25m.

  • 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.

Frequently asked questions about flying from Saint John to Chicago

  • How do I get Price Alerts for flights from Saint John to Chicago?

    Confirm your travel details to search for the latest offers for flights from Saint John to Chicago. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

  • How can I save money on flights from Saint John to Chicago with momondo?

    Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 29/8
Sat 5/9
By creating a price alert you accept our terms of use and privacy policy.

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