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Cheap flights from St. John's to Chicago from C$ 693

This is the cheapest round-trip 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 1/6. 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
1 adult, Economy, 0 bags

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

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:35 a.m. - 10:18 a.m.
YYT
-
ORD
7h 13m
1 stop
United Airlines Logo
8:40 a.m. - 12:36 a.m.
ORD
-
YYT
13h 26m
2 stops
C$ 693United Airlines
Mon, 1 Jun - Fri, 5 Jun
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:55 a.m.
MDW
-
YYT
7h 05m
2 stops
C$ 695Porter Airlines
Wed, 29 Jul - Wed, 5 Aug
United Airlines Logo
2:00 p.m. - 11:30 p.m.
YYT
-
ORD
12h 00m
2 stops
United Airlines Logo
11:03 a.m. - 12:36 a.m.
ORD
-
YYT
11h 03m
2 stops
C$ 702United Airlines
Mon, 1 Jun - Fri, 5 Jun
Air Canada Logo
5:35 a.m. - 10:18 a.m.
YYT
-
ORD
7h 13m
1 stop
Air Canada Logo
2:00 p.m. - 12:36 a.m.
ORD
-
YYT
8h 06m
2 stops
C$ 724Air Canada
Mon, 1 Jun - Fri, 5 Jun
Air Canada Logo
2:00 p.m. - 8:16 p.m.
YYT
-
ORD
8h 46m
2 stops
Air Canada Logo
2:00 p.m. - 12:36 a.m.
ORD
-
YYT
8h 06m
2 stops
C$ 725Air Canada
Mon, 1 Jun - Fri, 5 Jun
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
10:25 a.m. - 12:56 a.m.
MDW
-
YYT
12h 01m
2 stops
C$ 725Porter Airlines
Tue, 26 May - Fri, 29 May
Air Canada Logo
5:35 a.m. - 10:18 a.m.
YYT
-
ORD
7h 13m
1 stop
Air Canada Logo
2:00 p.m. - 12:36 a.m.
ORD
-
YYT
8h 06m
2 stops
C$ 726Air Canada
Mon, 1 Jun - Fri, 5 Jun
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:56 a.m.
MDW
-
YYT
7h 06m
2 stops
C$ 726Porter Airlines
Tue, 26 May - Fri, 29 May
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.
YYT
-
MDW
11h 00m
2 stops
Porter Airlines Logo
3:20 p.m. - 12:56 a.m.
MDW
-
YYT
7h 06m
2 stops
C$ 728Porter Airlines
Tue, 26 May - Fri, 29 May
Multiple Airlines Logo
4:00 p.m. - 9:40 a.m.
YYT
-
MDW
20h 10m
3 stops
Multiple Airlines Logo
1:00 p.m. - 12:55 a.m.
MDW
-
YYT
9h 25m
3 stops
C$ 1,384Multiple Airlines
Wed, 29 Jul - Wed, 5 Aug

United Airlines flights from St. John's to Chicago

Our best United Airlines deals on St. John's to Chicago flight tickets
United Airlines
1 Jun
YYT5:35 a.m.St John's
7h 13m
1 stop
ORD10:18 a.m.Chicago O'Hare Intl
5 Jun
ORD8:40 a.m.Chicago O'Hare Intl
13h 26m
2 stops
YYT12:36 a.m.St John's
C$ 693
United Airlines
1 Jun
YYT2:00 p.m.St John's
12h 00m
2 stops
ORD11:30 p.m.Chicago O'Hare Intl
5 Jun
ORD11:03 a.m.Chicago O'Hare Intl
11h 03m
2 stops
YYT12:36 a.m.St John's
C$ 702
United Airlines
29 Jul
YYT5:35 a.m.St John's
7h 11m
1 stop
ORD10:16 a.m.Chicago O'Hare Intl
5 Aug
ORD6:30 a.m.Chicago O'Hare Intl
15h 45m
2 stops
YYT12:45 a.m.St John's
C$ 843

WestJet flights from St. John's to Chicago

Our best WestJet deals on St. John's to Chicago flight tickets
WestJet
28 Mar
YYT3:00 p.m.St John's
29h 30m
2 stops
ORD6:00 p.m.Chicago O'Hare Intl
31 Mar
ORD7:00 p.m.Chicago O'Hare Intl
49h 28m
2 stops
YYT10:58 p.m.St John's
C$ 1,378
WestJet
28 Mar
YYT3:00 p.m.St John's
24h 55m
2 stops
MDW1:25 p.m.Chicago Midway
31 Mar
MDW7:20 p.m.Chicago Midway
49h 08m
2 stops
YYT10:58 p.m.St John's
C$ 1,560

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 19 March 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 - ORD

YYTORD

St John's

Mon 1/6

5:35 a.m.-10:18 a.m.

1 stop7h 13m

Chicago O'Hare Intl

Fri 5/6

8:40 a.m.-12:36 a.m.

2 stops13h 26m

C$ 693

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 29/7

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

2 stops11h 00m

Chicago Midway

Wed 5/8

3:20 p.m.-12:55 a.m.

2 stops7h 05m

C$ 695

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 1/6

2:00 p.m.-11:30 p.m.

2 stops12h 00m

Chicago O'Hare Intl

Fri 5/6

11:03 a.m.-12:36 a.m.

2 stops11h 03m

C$ 702
Quickest round-trip

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 1/6

5:35 a.m.-10:18 a.m.

1 stop7h 13m

Chicago O'Hare Intl

Fri 5/6

2:00 p.m.-12:36 a.m.

2 stops8h 06m

C$ 724

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 1/6

2:00 p.m.-8:16 p.m.

2 stops8h 46m

Chicago O'Hare Intl

Fri 5/6

2:00 p.m.-12:36 a.m.

2 stops8h 06m

C$ 725

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

Fri 29/5

10:25 a.m.-12:56 a.m.

2 stops12h 01m

C$ 725

St. John'sChicago

YYT - ORD

YYTORD

St John's

Mon 1/6

5:35 a.m.-10:18 a.m.

1 stop7h 13m

Chicago O'Hare Intl

Fri 5/6

2:00 p.m.-12:36 a.m.

2 stops8h 06m

C$ 726

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

Fri 29/5

3:20 p.m.-12:56 a.m.

2 stops7h 06m

C$ 726

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

Fri 29/5

3:20 p.m.-12:56 a.m.

2 stops7h 06m

C$ 728

St. John'sChicago

YYT - MDW

YYTMDW

St John's

Wed 29/7

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

3 stops20h 10m

Chicago Midway

Wed 5/8

1:00 p.m.-12:55 a.m.

3 stops9h 25m

C$ 1,384

Flights are sorted by cheapest round-trip flights first.

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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?

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

7h 13m

Direct flights

None
The fastest flight from St. John's to Chicago takes 7h 13m
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

  • 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 7h 13m.

  • 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
Munster
Hammond

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.

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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