What is the cheapest airline that flies from St John's to Chicago?

Air Canada and United Airlines are the most popular carriers operating from St John's to Chicago

When did momondo last update prices for flights from St John's Airport to Chicago?

Prices for flights from St John's Airport to Chicago were last updated today.

How many operators does momondo search for flights from St John's Airport to Chicago?

As of November 2025, there is 1 operator available to choose from for flights from St John's Airport to Chicago.

How old do you have to be to fly from St John's Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from St John's Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago 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. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 317 Cheap Flights from St. John's to Chicago in 2025/26

1 adult

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Find the cheapest flights from St. John's to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:05 a.m. - 11:18 a.m.YYT-ORD

8h 43m1 stop

7:05 a.m. - 5:21 p.m.ORD-YYT

7h 46m1 stop

C$ 640Air Canada

Find Deal

Thu, 4 Dec - Thu, 11 Dec

5:05 a.m. - 11:18 a.m.YYT-ORD

8h 43m1 stop

10:00 a.m. - 11:30 p.m.ORD-YYT

11h 00m2 stops

C$ 644Air Canada

Find Deal

Thu, 4 Dec - Thu, 11 Dec

5:05 a.m. - 1:01 p.m.YYT-ORD

10h 26m2 stops

8:00 a.m. - 8:15 p.m.ORD-YYT

9h 45m2 stops

C$ 651Air Canada

Find Deal

Thu, 4 Dec - Thu, 11 Dec

6:20 a.m. - 3:20 p.m.YYT-MDW

11h 30m2 stops

4:15 p.m. - 4:45 p.m.MDW-YYT

22h 00m1 stop

C$ 679Porter Airlines

Find Deal

Thu, 4 Dec - Thu, 11 Dec

5:05 a.m. - 1:01 p.m.YYT-ORD

10h 26m2 stops

7:15 a.m. - 8:15 p.m.ORD-YYT

10h 30m2 stops

C$ 685Air Canada

Find Deal

Wed, 31 Dec - Tue, 6 Jan

5:00 a.m. - 3:20 p.m.YYT-MDW

12h 50m1 stop

11:00 a.m. - 11:33 p.m.MDW-YYT

10h 03m1 stop

C$ 1,023Multiple Airlines

Find Deal

Thu, 4 Dec - Thu, 11 Dec

Air Canada flights from St. John's to Chicago

Our best Air Canada deals on St. John's to Chicago flight tickets

Air Canada

4 Dec

YYT5:05 a.m.St John's

8h 43m

1 stop

ORD11:18 a.m.Chicago O'Hare Intl

11 Dec

ORD7:05 a.m.Chicago O'Hare Intl

7h 46m

1 stop

YYT5:21 p.m.St John's

C$ 640

Find similar

Air Canada

4 Dec

YYT5:05 a.m.St John's

8h 43m

1 stop

ORD11:18 a.m.Chicago O'Hare Intl

11 Dec

ORD10:00 a.m.Chicago O'Hare Intl

11h 00m

2 stops

YYT11:30 p.m.St John's

C$ 644

Find similar

Air Canada

4 Dec

YYT5:05 a.m.St John's

10h 26m

2 stops

ORD1:01 p.m.Chicago O'Hare Intl

11 Dec

ORD8:00 a.m.Chicago O'Hare Intl

9h 45m

2 stops

YYT8:15 p.m.St John's

C$ 651

Find similar

Fly from

Fly to

Route

Depart

Return

Price

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 4/12

5:05 a.m.-11:18 a.m.

1 stop8h 43m

Chicago O'Hare Intl

Thu 11/12

7:05 a.m.-5:21 p.m.

1 stop7h 46m

C$ 640

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 4/12

5:05 a.m.-11:18 a.m.

1 stop8h 43m

Chicago O'Hare Intl

Thu 11/12

10:00 a.m.-11:30 p.m.

2 stops11h 00m

C$ 644

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 4/12

5:05 a.m.-1:01 p.m.

2 stops10h 26m

Chicago O'Hare Intl

Thu 11/12

8:00 a.m.-8:15 p.m.

2 stops9h 45m

C$ 651

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/12

6:20 a.m.-3:20 p.m.

2 stops11h 30m

Chicago Midway

Thu 11/12

4:15 p.m.-4:45 p.m.

1 stop22h 00m

C$ 679

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 31/12

5:05 a.m.-1:01 p.m.

2 stops10h 26m

Chicago O'Hare Intl

Tue 6/1

7:15 a.m.-8:15 p.m.

2 stops10h 30m

C$ 685

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 4/12

5:00 a.m.-3:20 p.m.

1 stop12h 50m

Chicago Midway

Thu 11/12

11:00 a.m.-11:33 p.m.

1 stop10h 03m

C$ 1,023

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 11/4

5:25 a.m.-10:08 a.m.

1 stop7h 13m

C$ 377

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 11/4

5:25 a.m.-11:12 p.m.

2 stops20h 17m

C$ 420

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sat 11/4

6:00 a.m.-1:45 p.m.

3 stops34h 15m

C$ 545

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

How to get the cheapest flight ticket from St. John's 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

Prices

Airlines

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 713. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 885. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the morning is the cheapest time of day to fly from St. John's to Chicago when you can find flight prices for as low as C$ 713. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 838 per ticket.

When to book flights from St. John's to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from St. John's to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap St. John's to Chicago (YYT to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from St. John's to Chicago

Direct flights	None

There are no direct flights from St. John's to Chicago. There are no popular flight routes from St. John's to Chicago.

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How far is St John's to Chicago by plane?
The straight-line distance from St John's to Chicago is 2803.2 km. A reasonable flight in good conditions will take 8h 43m.
When did momondo last update prices for flights from St John's Airport to Chicago?
Prices for flights from St John's Airport to Chicago were last updated today.
How many operators does momondo search for flights from St John's Airport to Chicago?
As of November 2025, there is 1 operator available to choose from for flights from St John's Airport to Chicago.
How old do you have to be to fly from St John's Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from St John's Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from St. John's to Chicago

Compare and see reviews for airlines that fly from St. John's to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 692	Free Cancellation	Rating 7.1 10,398 reviews		Search Air Canada flights

Munster

Hammond

Merrillville

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Why should I use momondo to find a flight deal from St. John's to Chicago?

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Can I find flights from St. John's to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for St. John's to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from St. John's 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 St. John's.

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

Of course. momondo tracks the price of St. John's to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.