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Cheap flights from Saint John to Chicago from C$ 790

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 26/9. 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 p.m. - 8:12 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 32m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada 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$ 790Air Canada
Sat, 26 Sep - Tue, 29 Sep
Air Canada Logo
4:40 p.m. - 8:12 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 32m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada 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$ 791Air Canada
Sat, 26 Sep - Tue, 29 Sep
Air Canada Logo
4:40 p.m. - 8:12 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 32m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada 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$ 793Air Canada
Sat, 26 Sep - Tue, 29 Sep
Air Canada Logo
12:50 p.m. - 4:58 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
Air Canada 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$ 798Air Canada
Thu, 10 Sep - Mon, 14 Sep
Air Canada Logo
4:40 p.m. - 8:12 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 32m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada 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$ 800Air Canada
Thu, 17 Sep - Thu, 24 Sep
Air Canada Logo
4:40 p.m. - 8:05 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
5h 25m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:40 a.m. - 4:00 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 20m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 819Air Canada
Fri, 28 Aug - Mon, 31 Aug
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
11:45 a.m. - 10:00 a.m.MDW  Chicago Midway-YSJ Saint John
20h 15m1 stop Toronto Island
C$ 822Multiple Airlines
Fri, 28 Aug - Tue, 1 Sep
Air Canada Logo
12:50 p.m. - 4:58 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
Air Canada Logo
9:00 a.m. - 11:51 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
12h 51m2 stops Newark Toronto Pearson Intl
C$ 852Air Canada
Sat, 26 Sep - Tue, 29 Sep
Air Canada Logo
5:00 a.m. - 9:00 a.m.YSJ  Saint John-ORD Chicago O'Hare Intl
6h 00m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 a.m. - 4:00 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
5h 20m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 853Air Canada
Sun, 23 Aug - Sun, 30 Aug
Air Canada Logo
12:50 p.m. - 4:58 p.m.YSJ  Saint John-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
Air Canada Logo
9:00 a.m. - 11:51 p.m.ORD  Chicago O'Hare Intl-YSJ Saint John
12h 51m2 stops Newark Toronto Pearson Intl
C$ 855Air Canada
Sat, 26 Sep - Tue, 29 Sep

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United Airlines flights from Saint John to Chicago

Our best United Airlines deals on Saint John to Chicago flight tickets
United Airlines
17 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
24 Sep
ORD5:00 a.m.Chicago O'Hare Intl
8h 59m
2 stops
YSJ3:59 p.m.Saint John
C$ 876
United Airlines
28 Aug
YSJ5:00 a.m.Saint John
10h 13m
2 stops
ORD1:13 p.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$ 918
United Airlines
23 Aug
YSJ5:00 a.m.Saint John
11h 21m
2 stops
ORD2:21 p.m.Chicago O'Hare Intl
30 Aug
ORD6:00 a.m.Chicago O'Hare Intl
8h 00m
2 stops
YSJ4:00 p.m.Saint John
C$ 946

Air Canada flights from Saint John to Chicago

Our best Air Canada deals on Saint John to Chicago flight tickets
Air Canada
26 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
29 Sep
ORD8:45 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ3:59 p.m.Saint John
C$ 790
Air Canada
26 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
29 Sep
ORD8:45 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ3:59 p.m.Saint John
C$ 791
Air Canada
26 Sep
YSJ4:40 p.m.Saint John
5h 32m
1 stop
ORD8:12 p.m.Chicago O'Hare Intl
29 Sep
ORD8:45 a.m.Chicago O'Hare Intl
5h 14m
1 stop
YSJ3:59 p.m.Saint John
C$ 793

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 5 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 26/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Tue 29/9

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

1 stop5h 14m

C$ 790

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 26/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Tue 29/9

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

1 stop5h 14m

C$ 791

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 26/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Tue 29/9

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

1 stop5h 14m

C$ 793

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Thu 10/9

12:50 p.m.-4:58 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Mon 14/9

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

1 stop5h 14m

C$ 798

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Thu 17/9

4:40 p.m.-8:12 p.m.

1 stop5h 32m

Chicago O'Hare Intl

Thu 24/9

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

1 stop5h 14m

C$ 800
Quickest round-trip

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

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$ 819

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

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

1 stop20h 15m

C$ 822

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 26/9

12:50 p.m.-4:58 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Tue 29/9

9:00 a.m.-11:51 p.m.

2 stops12h 51m

C$ 852

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

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$ 853

Saint JohnChicago

YSJ Saint John - ORD Chicago O'Hare Intl

YSJORD

Saint John

Sat 26/9

12:50 p.m.-4:58 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Tue 29/9

9:00 a.m.-11:51 p.m.

2 stops12h 51m

C$ 855

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 32m

Direct flights

None
The fastest flight from Saint John to Chicago takes 5h 32m
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 32m.

  • 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.

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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