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Cheap flights from Chicago to St. John's from C$ 203

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to St. John's departing on 18/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to St. John's (CHI-YYT)

Cheap round-trip flights

WestJet Logo
1:40 p.m. - 6:20 a.m.ORD-YYT
14h 10m2 stops
WestJet Logo
7:10 a.m. - 4:43 p.m.YYT-ORD
12h 03m1 stop
C$ 427WestJet
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Logo
6:00 a.m. - 2:30 p.m.ORD-YYT
30h 00m1 stop
Logo
5:40 p.m. - 11:44 p.m.YYT-ORD
32h 34m2 stops
C$ 517
Find Deal
Sun, 19 Oct - Sun, 26 Oct
WestJet Logo
5:30 p.m. - 10:56 p.m.ORD-YYT
26h 56m2 stops
WestJet Logo
7:10 a.m. - 1:35 p.m.YYT-ORD
32h 55m1 stop
C$ 522WestJet
Find Deal
Sat, 18 Oct - Sat, 25 Oct
WestJet Logo
5:30 p.m. - 6:20 a.m.ORD-YYT
34h 20m1 stop
WestJet Logo
7:10 a.m. - 1:35 p.m.YYT-ORD
32h 55m1 stop
C$ 532WestJet
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
Porter Airlines Logo
6:00 a.m. - 3:20 p.m.YYT-MDW
11h 50m2 stops
C$ 566Porter Airlines
Find Deal
Sun, 19 Oct - Sun, 26 Oct
Porter Airlines Logo
9:35 a.m. - 12:38 a.m.MDW-YYT
12h 33m2 stops
Porter Airlines Logo
7:00 a.m. - 4:24 p.m.YYT-MDW
11h 54m3 stops
C$ 580Porter Airlines
Find Deal
Wed, 15 Oct - Wed, 22 Oct
Air Canada Logo
3:50 p.m. - 1:16 a.m.ORD-YYT
6h 56m1 stop
Air Canada Logo
5:00 a.m. - 9:09 a.m.YYT-ORD
6h 39m1 stop
C$ 685Air Canada
Find Deal
Tue, 7 Oct - Thu, 9 Oct
Air Canada Logo
2:00 p.m. - 1:16 a.m.ORD-YYT
8h 46m1 stop
Air Canada Logo
8:45 a.m. - 1:14 p.m.YYT-ORD
6h 59m1 stop
C$ 698Air Canada
Find Deal
Mon, 29 Sep - Sun, 5 Oct
United Airlines Logo
3:35 p.m. - 12:39 a.m.ORD-YYT
6h 34m1 stop
United Airlines Logo
5:50 a.m. - 11:23 a.m.YYT-ORD
8h 03m1 stop
C$ 823United Airlines
Find Deal
Sat, 18 Oct - Sat, 25 Oct
United Airlines Logo
8:00 a.m. - 12:39 a.m.ORD-YYT
14h 09m2 stops
United Airlines Logo
2:00 p.m. - 8:22 p.m.YYT-ORD
8h 52m1 stop
C$ 829United Airlines
Find Deal
Wed, 15 Oct - Wed, 22 Oct

WestJet flights from Chicago to St. John's

Our best WestJet deals on Chicago to St. John's flight tickets
WestJet
18 Oct
ORD1:40 p.m.Chicago O'Hare Intl
14h 10m
2 stops
YYT6:20 a.m.St John's
25 Oct
YYT7:10 a.m.St John's
12h 03m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
C$ 427
Find similar
WestJet
18 Oct
ORD5:30 p.m.Chicago O'Hare Intl
26h 56m
2 stops
YYT10:56 p.m.St John's
25 Oct
YYT7:10 a.m.St John's
32h 55m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
C$ 522
Find similar
WestJet
18 Oct
ORD5:30 p.m.Chicago O'Hare Intl
34h 20m
1 stop
YYT6:20 a.m.St John's
25 Oct
YYT7:10 a.m.St John's
32h 55m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
C$ 532
Find similar

Porter Airlines flights from Chicago to St. John's

Our best Porter Airlines deals on Chicago to St. John's flight tickets
Porter Airlines
19 Oct
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
26 Oct
YYT6:00 a.m.St John's
11h 50m
2 stops
MDW3:20 p.m.Chicago Midway
C$ 566
Find similar
Porter Airlines
15 Oct
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
22 Oct
YYT7:00 a.m.St John's
11h 54m
3 stops
MDW4:24 p.m.Chicago Midway
C$ 580
Find similar
Porter Airlines
17 Oct
MDW9:35 a.m.Chicago Midway
12h 33m
2 stops
YYT12:38 a.m.St John's
24 Oct
YYT2:55 p.m.St John's
20h 14m
3 stops
MDW8:39 a.m.Chicago Midway
C$ 598
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to St. John's 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 4 September 2025.
Use the filters below to find and compare flights from Chicago to St. John's that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 18/10

1:40 p.m.-6:20 a.m.

2 stops14h 10m

St John's

Sat 25/10

7:10 a.m.-4:43 p.m.

1 stop12h 03m

C$ 427

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sun 19/10

6:00 a.m.-2:30 p.m.

1 stop30h 00m

St John's

Sun 26/10

5:40 p.m.-11:44 p.m.

2 stops32h 34m

C$ 517

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 18/10

5:30 p.m.-10:56 p.m.

2 stops26h 56m

St John's

Sat 25/10

7:10 a.m.-1:35 p.m.

1 stop32h 55m

C$ 522

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 18/10

5:30 p.m.-6:20 a.m.

1 stop34h 20m

St John's

Sat 25/10

7:10 a.m.-1:35 p.m.

1 stop32h 55m

C$ 532

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Sun 19/10

9:35 a.m.-12:38 a.m.

2 stops12h 33m

St John's

Sun 26/10

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

2 stops11h 50m

C$ 566

ChicagoSt. John's

MDW - YYT

MDWYYT

Chicago Midway

Wed 15/10

9:35 a.m.-12:38 a.m.

2 stops12h 33m

St John's

Wed 22/10

7:00 a.m.-4:24 p.m.

3 stops11h 54m

C$ 580

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Tue 7/10

3:50 p.m.-1:16 a.m.

1 stop6h 56m

St John's

Thu 9/10

5:00 a.m.-9:09 a.m.

1 stop6h 39m

C$ 685

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Mon 29/9

2:00 p.m.-1:16 a.m.

1 stop8h 46m

St John's

Sun 5/10

8:45 a.m.-1:14 p.m.

1 stop6h 59m

C$ 698

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Sat 18/10

3:35 p.m.-12:39 a.m.

1 stop6h 34m

St John's

Sat 25/10

5:50 a.m.-11:23 a.m.

1 stop8h 03m

C$ 823

ChicagoSt. John's

ORD - YYT

ORDYYT

Chicago O'Hare Intl

Wed 15/10

8:00 a.m.-12:39 a.m.

2 stops14h 09m

St John's

Wed 22/10

2:00 p.m.-8:22 p.m.

1 stop8h 52m

C$ 829

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to St. John's from

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

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 Chicago to St John's?

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

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

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

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

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

Direct flights

None
There are no direct flights from Chicago to St. John's. There are no popular flight routes from Chicago to St. John's.
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  • How far is Chicago to St John's by plane?

    The distance between Chicago and St John's is about 2803.2 km. Typically, this will take 5h 59m by plane in normal conditions.

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

    Prices for flights from Chicago to St John's Airport are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to St John's Airport.

  • What documentation or ID do you need to fly to St John's Airport?

    The necessary travel and health documents for your St John's Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

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

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

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

momondo does allow users to show only those flights to St. John's from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

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 St. John's from Chicago.

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

Price alerts on flights to St. John's from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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