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

Air Canada is the most popular carrier 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 July 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$ 302 Cheap Flights from St. John's to Chicago in 2025

1 adult

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

Round-trip

One-way

Cheap round-trip flights

5:10 a.m. - 11:18 a.m.YYT-ORD

8h 38m1 stop

2:00 p.m. - 11:13 p.m.ORD-YYT

6h 43m1 stop

C$ 595Air Canada

Find Deal

Wed, 10 Dec - Mon, 15 Dec

6:00 a.m. - 3:20 p.m.YYT-MDW

11h 50m3 stops

11:00 a.m. - 11:05 p.m.MDW-YYT

9h 35m3 stops

C$ 599Porter Airlines

Find Deal

Wed, 10 Dec - Mon, 15 Dec

6:50 a.m. - 1:01 p.m.YYT-ORD

8h 41m1 stop

3:55 p.m. - 1:33 a.m.ORD-YYT

7h 08m1 stop

C$ 603Air Canada

Find Deal

Thu, 11 Dec - Mon, 15 Dec

5:50 a.m. - 9:51 a.m.YYT-ORD

6h 31m1 stop

8:40 a.m. - 5:09 p.m.ORD-YYT

5h 59m1 stop

C$ 642Air Canada

Find Deal

Tue, 9 Sep - Fri, 12 Sep

5:50 a.m. - 9:51 a.m.YYT-ORD

6h 31m1 stop

8:40 a.m. - 5:09 p.m.ORD-YYT

5h 59m1 stop

C$ 645Air Canada

Find Deal

Sun, 14 Sep - Sun, 21 Sep

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

11h 30m2 stops

11:00 a.m. - 11:05 p.m.MDW-YYT

9h 35m2 stops

C$ 659Porter Airlines

Find Deal

Thu, 11 Dec - Mon, 15 Dec

3:00 p.m. - 6:46 p.m.YYT-ORD

30h 16m2 stops

6:20 p.m. - 10:56 p.m.ORD-YYT

26h 06m2 stops

C$ 703WestJet

Find Deal

Wed, 17 Sep - Sat, 20 Sep

3:00 p.m. - 9:40 a.m.YYT-MDW

45h 10m2 stops

11:00 a.m. - 10:56 p.m.MDW-YYT

9h 26m2 stops

C$ 732WestJet

Find Deal

Wed, 17 Sep - Sat, 20 Sep

5:50 a.m. - 9:51 a.m.YYT-ORD

6h 31m1 stop

9:00 a.m. - 12:39 a.m.ORD-YYT

13h 09m2 stops

C$ 736United Airlines

Find Deal

Tue, 9 Sep - Fri, 12 Sep

5:50 a.m. - 1:08 p.m.YYT-ORD

9h 48m2 stops

6:00 a.m. - 12:39 a.m.ORD-YYT

16h 09m2 stops

C$ 745United Airlines

Find Deal

Tue, 9 Sep - Fri, 12 Sep

Air Canada flights from St. John's to Chicago

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

Air Canada

10 Dec

YYT5:10 a.m.St John's

8h 38m

1 stop

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

15 Dec

ORD2:00 p.m.Chicago O'Hare Intl

6h 43m

1 stop

YYT11:13 p.m.St John's

C$ 595

Find similar

Air Canada

11 Dec

YYT6:50 a.m.St John's

8h 41m

1 stop

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

15 Dec

ORD3:55 p.m.Chicago O'Hare Intl

7h 08m

1 stop

YYT1:33 a.m.St John's

C$ 603

Find similar

Air Canada

9 Sep

YYT5:50 a.m.St John's

6h 31m

1 stop

ORD9:51 a.m.Chicago O'Hare Intl

12 Sep

ORD8:40 a.m.Chicago O'Hare Intl

5h 59m

1 stop

YYT5:09 p.m.St John's

C$ 642

Find similar

United Airlines flights from St. John's to Chicago

Our best United Airlines deals on St. John's to Chicago flight tickets

United Airlines

9 Sep

YYT5:50 a.m.St John's

6h 31m

1 stop

ORD9:51 a.m.Chicago O'Hare Intl

12 Sep

ORD9:00 a.m.Chicago O'Hare Intl

13h 09m

2 stops

YYT12:39 a.m.St John's

C$ 736

Find similar

United Airlines

9 Sep

YYT5:50 a.m.St John's

9h 48m

2 stops

ORD1:08 p.m.Chicago O'Hare Intl

12 Sep

ORD6:00 a.m.Chicago O'Hare Intl

16h 09m

2 stops

YYT12:39 a.m.St John's

C$ 745

Find similar

United Airlines

10 Dec

YYT5:10 a.m.St John's

8h 38m

1 stop

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

15 Dec

ORD11:00 a.m.Chicago O'Hare Intl

12h 03m

2 stops

YYT1:33 a.m.St John's

C$ 750

Find similar

Fly from

Fly to

Route

Depart

Return

Price

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 10/12

5:10 a.m.-11:18 a.m.

1 stop8h 38m

Chicago O'Hare Intl

Mon 15/12

2:00 p.m.-11:13 p.m.

1 stop6h 43m

C$ 595

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 10/12

6:00 a.m.-3:20 p.m.

3 stops11h 50m

Chicago Midway

Mon 15/12

11:00 a.m.-11:05 p.m.

3 stops9h 35m

C$ 599

St. John'sChicago

YYT - ORD

YYTORD

St John's

Thu 11/12

6:50 a.m.-1:01 p.m.

1 stop8h 41m

Chicago O'Hare Intl

Mon 15/12

3:55 p.m.-1:33 a.m.

1 stop7h 08m

C$ 603

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 9/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

Chicago O'Hare Intl

Fri 12/9

8:40 a.m.-5:09 p.m.

1 stop5h 59m

C$ 642

St. John'sChicago

YYT - ORD

YYTORD

St John's

Sun 14/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

Chicago O'Hare Intl

Sun 21/9

8:40 a.m.-5:09 p.m.

1 stop5h 59m

C$ 645

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Thu 11/12

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

2 stops11h 30m

Chicago Midway

Mon 15/12

11:00 a.m.-11:05 p.m.

2 stops9h 35m

C$ 659

St. John'sChicago

YYT - ORD

YYTORD

St John's

Wed 17/9

3:00 p.m.-6:46 p.m.

2 stops30h 16m

Chicago O'Hare Intl

Sat 20/9

6:20 p.m.-10:56 p.m.

2 stops26h 06m

C$ 703

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 17/9

3:00 p.m.-9:40 a.m.

2 stops45h 10m

Chicago Midway

Sat 20/9

11:00 a.m.-10:56 p.m.

2 stops9h 26m

C$ 732

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 9/9

5:50 a.m.-9:51 a.m.

1 stop6h 31m

Chicago O'Hare Intl

Fri 12/9

9:00 a.m.-12:39 a.m.

2 stops13h 09m

C$ 736

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 9/9

5:50 a.m.-1:08 p.m.

2 stops9h 48m

Chicago O'Hare Intl

Fri 12/9

6:00 a.m.-12:39 a.m.

2 stops16h 09m

C$ 745

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted 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$ 704. 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$ 874. 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$ 704. 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$ 828 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

Best price found	C$ 302
Fastest flight time	6h 31m
Direct flights	None
Airports in Chicago	2 airports

The best one-way flight to Chicago from St. John's in the past 72 hours is C$ 302. The best round-trip flight deal from St. John's to Chicago found on momondo in the last 72 hours is C$ 595.

The fastest flight from St. John's to Chicago takes 6h 31m

There are no direct flights from St. John's to Chicago. Popular non-direct routes for this connection are St John's Airport - Chicago Midway Airport and St John's Airport - Chicago O'Hare Intl Airport.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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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 6h 31m.
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 July 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$ 636	Free Cancellation	Rating 7.1 9,851 reviews		Search Air Canada flights

Hammond

Munster

Benton Harbor

Merrillville

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from St. John's to Chicago. momondo saves you time and could save you money on your trip.

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.