Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from St. John's to Chicago from C$ 361

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from St. John's to Chicago departing on 14/6. 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

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

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

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:30 a.m. - 12:55 a.m.
MDW
-
YYT
11h 55m
2 stops
C$ 681Porter Airlines
Tue, 12 May - Tue, 19 May
Air Canada Logo
5:35 a.m. - 1:10 p.m.
YYT
-
ORD
10h 05m
2 stops
Air Canada Logo
8:45 a.m. - 11:28 p.m.
ORD
-
YYT
12h 13m
2 stops
C$ 715Air Canada
Mon, 31 Aug - Thu, 3 Sep
Air Canada Logo
5:35 a.m. - 1:10 p.m.
YYT
-
ORD
10h 05m
2 stops
Air Canada Logo
8:45 a.m. - 11:28 p.m.
ORD
-
YYT
12h 13m
2 stops
C$ 716Air Canada
Mon, 31 Aug - Thu, 3 Sep
Air Canada Logo
5:35 a.m. - 1:10 p.m.
YYT
-
ORD
10h 05m
2 stops
Air Canada Logo
8:45 a.m. - 11:28 p.m.
ORD
-
YYT
12h 13m
2 stops
C$ 718Air Canada
Mon, 31 Aug - Thu, 3 Sep
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:15 a.m. - 12:56 a.m.
MDW
-
YYT
12h 11m
2 stops
C$ 769Porter Airlines
Tue, 26 May - Tue, 2 Jun
Air Canada Logo
5:35 a.m. - 1:25 p.m.
YYT
-
ORD
10h 20m
2 stops
Air Canada Logo
8:20 p.m. - 1:18 p.m.
ORD
-
YYT
14h 28m
2 stops
C$ 769Air Canada
Tue, 26 May - Tue, 2 Jun
Air Canada Logo
5:35 a.m. - 1:10 p.m.
YYT
-
ORD
10h 05m
2 stops
Air Canada Logo
9:50 a.m. - 1:46 a.m.
ORD
-
YYT
13h 26m
1 stop
C$ 772Air Canada
Mon, 31 Aug - Thu, 3 Sep
Air Canada Logo
5:35 a.m. - 1:10 p.m.
YYT
-
ORD
10h 05m
2 stops
Air Canada Logo
9:50 a.m. - 1:46 a.m.
ORD
-
YYT
13h 26m
1 stop
C$ 773Air Canada
Mon, 31 Aug - Thu, 3 Sep
Air Canada Logo
5:35 a.m. - 1:10 p.m.
YYT
-
ORD
10h 05m
2 stops
Air Canada Logo
9:50 a.m. - 1:46 a.m.
ORD
-
YYT
13h 26m
1 stop
C$ 775Air Canada
Mon, 31 Aug - Thu, 3 Sep
Delta Logo
3:00 p.m. - 1:11 p.m.
YYT
-
MDW
24h 41m
2 stops
Delta Logo
5:59 p.m. - 10:55 p.m.
MDW
-
YYT
26h 26m
2 stops
C$ 1,146Delta
Tue, 15 Sep - Sat, 19 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
31 Aug
YYT5:35 a.m.St John's
10h 05m
2 stops
ORD1:10 p.m.Chicago O'Hare Intl
3 Sep
ORD8:45 a.m.Chicago O'Hare Intl
12h 13m
2 stops
YYT11:28 p.m.St John's
C$ 715
Air Canada
31 Aug
YYT5:35 a.m.St John's
10h 05m
2 stops
ORD1:10 p.m.Chicago O'Hare Intl
3 Sep
ORD8:45 a.m.Chicago O'Hare Intl
12h 13m
2 stops
YYT11:28 p.m.St John's
C$ 716
Air Canada
31 Aug
YYT5:35 a.m.St John's
10h 05m
2 stops
ORD1:10 p.m.Chicago O'Hare Intl
3 Sep
ORD8:45 a.m.Chicago O'Hare Intl
12h 13m
2 stops
YYT11:28 p.m.St John's
C$ 718

United Airlines flights from St. John's to Chicago

Our best United Airlines deals on St. John's to Chicago flight tickets
United Airlines
13 Jun
YYT5:35 a.m.St John's
7h 13m
1 stop
ORD10:18 a.m.Chicago O'Hare Intl
20 Jun
ORD11:03 a.m.Chicago O'Hare Intl
11h 12m
2 stops
YYT12:45 a.m.St John's
C$ 847
United Airlines
26 May
YYT5:40 p.m.St John's
6h 55m
1 stop
ORD10:05 p.m.Chicago O'Hare Intl
2 Jun
ORD7:40 p.m.Chicago O'Hare Intl
14h 51m
2 stops
YYT1:01 p.m.St John's
C$ 874
United Airlines
26 May
YYT2:05 p.m.St John's
8h 33m
1 stop
ORD8:08 p.m.Chicago O'Hare Intl
2 Jun
ORD7:40 p.m.Chicago O'Hare Intl
14h 51m
2 stops
YYT1:01 p.m.St John's
C$ 939

momondo Fare Finder

 
Customize your flight search to find flights from St. John's 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 1 May 2026.
Use the filters below to find and compare flights from St. John's to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 12/5

6:05 a.m.-2:35 p.m.

2 stops11h 00m

Chicago Midway

Tue 19/5

10:30 a.m.-12:55 a.m.

2 stops11h 55m

C$ 681
Quickest round-trip

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

8:45 a.m.-11:28 p.m.

2 stops12h 13m

C$ 715

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

8:45 a.m.-11:28 p.m.

2 stops12h 13m

C$ 716

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

8:45 a.m.-11:28 p.m.

2 stops12h 13m

C$ 718

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 26/5

6:05 a.m.-2:35 p.m.

2 stops11h 00m

Chicago Midway

Tue 2/6

10:15 a.m.-12:56 a.m.

2 stops12h 11m

C$ 769

St. John'sChicago

YYT - ORD

YYTORD

St John's

Tue 26/5

5:35 a.m.-1:25 p.m.

2 stops10h 20m

Chicago O'Hare Intl

Tue 2/6

8:20 p.m.-1:18 p.m.

2 stops14h 28m

C$ 769

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

9:50 a.m.-1:46 a.m.

1 stop13h 26m

C$ 772

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

9:50 a.m.-1:46 a.m.

1 stop13h 26m

C$ 773

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 31/8

5:35 a.m.-1:10 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Thu 3/9

9:50 a.m.-1:46 a.m.

1 stop13h 26m

C$ 775

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Tue 15/9

3:00 p.m.-1:11 p.m.

2 stops24h 41m

Chicago Midway

Sat 19/9

5:59 p.m.-10:55 p.m.

2 stops26h 26m

C$ 1,146

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

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

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

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

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

Fastest flight time

10h 45m

Direct flights

None
The fastest flight from St. John's to Chicago takes 10h 45m
There are no direct flights from St. John's to Chicago. There are no popular flight routes from St. John's to Chicago.
Search flight deals

Frequently asked questions about flying from St. John's to Chicago

  • 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 10h 45m.

  • 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 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.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

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.

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
Sun 31/5
Sun 7/6
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