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Cheap flights from Chicago to St. John's from C$ 625

This is the cheapest round-trip 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 11/9. 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

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

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 00m2 stops Ottawa Toronto Island
C$ 625Porter Airlines
Fri, 11 Sep - Fri, 18 Sep
Multiple Airlines Logo
11:45 a.m. - 12:35 p.m.MDW  Chicago Midway-YYT St John's
22h 20m1 stop Toronto Island
Multiple Airlines Logo
8:45 a.m. - 11:00 a.m.YYT  St John's-MDW Chicago Midway
28h 45m2 stops Halifax Intl Toronto Pearson Intl
C$ 644Multiple Airlines
Tue, 8 Sep - Tue, 15 Sep
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
Porter Airlines Logo
6:05 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 00m2 stops Ottawa Toronto Island
C$ 693Porter Airlines
Thu, 3 Sep - Sun, 6 Sep
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
C$ 719Porter Airlines
Mon, 21 Sep - Fri, 25 Sep
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
C$ 719Porter Airlines
Fri, 11 Sep - Tue, 15 Sep
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
C$ 737Porter Airlines
Tue, 1 Sep - Sat, 5 Sep
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
C$ 743Porter Airlines
Tue, 8 Sep - Tue, 15 Sep
Air Canada Logo
3:45 p.m. - 1:46 a.m.ORD  Chicago O'Hare Intl-YYT St John's
7h 31m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 9:53 a.m.YYT  St John's-ORD Chicago O'Hare Intl
7h 23m1 stop Toronto Pearson Intl
C$ 778Air Canada
Tue, 1 Sep - Sat, 5 Sep
Air Canada Logo
3:45 p.m. - 1:46 a.m.ORD  Chicago O'Hare Intl-YYT St John's
7h 31m1 stop Toronto Pearson Intl
Air Canada Logo
5:00 a.m. - 9:53 a.m.YYT  St John's-ORD Chicago O'Hare Intl
7h 23m1 stop Toronto Pearson Intl
C$ 799Air Canada
Thu, 3 Sep - Sun, 6 Sep
Porter Airlines Logo
11:45 a.m. - 12:55 a.m.MDW  Chicago Midway-YYT St John's
10h 40m2 stops Toronto Island Ottawa
Porter Airlines Logo
6:00 a.m. - 2:35 p.m.YYT  St John's-MDW Chicago Midway
11h 05m2 stops Montreal St Hubert Toronto Island
C$ 799Porter Airlines
Thu, 24 Sep - Thu, 1 Oct

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Air Canada flights from Chicago to St. John's

Our best Air Canada deals on Chicago to St. John's flight tickets
Air Canada
1 Sep
ORD3:45 p.m.Chicago O'Hare Intl
7h 31m
1 stop
YYT1:46 a.m.St John's
5 Sep
YYT5:00 a.m.St John's
7h 23m
1 stop
ORD9:53 a.m.Chicago O'Hare Intl
C$ 778
Air Canada
3 Sep
ORD3:45 p.m.Chicago O'Hare Intl
7h 31m
1 stop
YYT1:46 a.m.St John's
6 Sep
YYT5:00 a.m.St John's
7h 23m
1 stop
ORD9:53 a.m.Chicago O'Hare Intl
C$ 799
Air Canada
8 Sep
ORD3:45 p.m.Chicago O'Hare Intl
7h 31m
1 stop
YYT1:46 a.m.St John's
15 Sep
YYT5:00 a.m.St John's
9h 30m
1 stop
ORD12:00 p.m.Chicago O'Hare Intl
C$ 814

Porter Airlines flights from Chicago to St. John's

Our best Porter Airlines deals on Chicago to St. John's flight tickets
Porter Airlines
11 Sep
MDW11:45 a.m.Chicago Midway
10h 40m
2 stops
YYT12:55 a.m.St John's
18 Sep
YYT6:05 a.m.St John's
11h 00m
2 stops
MDW2:35 p.m.Chicago Midway
C$ 625
Porter Airlines
3 Sep
MDW11:45 a.m.Chicago Midway
10h 40m
2 stops
YYT12:55 a.m.St John's
6 Sep
YYT6:05 a.m.St John's
11h 00m
2 stops
MDW2:35 p.m.Chicago Midway
C$ 693
Porter Airlines
11 Sep
MDW11:45 a.m.Chicago Midway
10h 40m
2 stops
YYT12:55 a.m.St John's
15 Sep
YYT6:00 a.m.St John's
11h 05m
2 stops
MDW2:35 p.m.Chicago Midway
C$ 719

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 14 August 2026.
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

Cheapest round-trip

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Fri 11/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

St John's

Fri 18/9

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

2 stops11h 00m

C$ 625

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Tue 8/9

11:45 a.m.-12:35 p.m.

1 stop22h 20m

St John's

Tue 15/9

8:45 a.m.-11:00 a.m.

2 stops28h 45m

C$ 644

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Thu 3/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

St John's

Sun 6/9

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

2 stops11h 00m

C$ 693

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Mon 21/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

St John's

Fri 25/9

6:00 a.m.-2:35 p.m.

2 stops11h 05m

C$ 719

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Fri 11/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

St John's

Tue 15/9

6:00 a.m.-2:35 p.m.

2 stops11h 05m

C$ 719

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Tue 1/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

St John's

Sat 5/9

6:00 a.m.-2:35 p.m.

2 stops11h 05m

C$ 737

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Tue 8/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

St John's

Tue 15/9

6:00 a.m.-2:35 p.m.

2 stops11h 05m

C$ 743
Quickest round-trip

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Tue 1/9

3:45 p.m.-1:46 a.m.

1 stop7h 31m

St John's

Sat 5/9

5:00 a.m.-9:53 a.m.

1 stop7h 23m

C$ 778

ChicagoSt. John's

ORD Chicago O'Hare Intl - YYT St John's

ORDYYT

Chicago O'Hare Intl

Thu 3/9

3:45 p.m.-1:46 a.m.

1 stop7h 31m

St John's

Sun 6/9

5:00 a.m.-9:53 a.m.

1 stop7h 23m

C$ 799

ChicagoSt. John's

MDW Chicago Midway - YYT St John's

MDWYYT

Chicago Midway

Thu 24/9

11:45 a.m.-12:55 a.m.

2 stops10h 40m

St John's

Thu 1/10

6:00 a.m.-2:35 p.m.

2 stops11h 05m

C$ 799

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

Fastest flight time

6h 00m

Direct flights

None
The fastest flight from Chicago to St. John's takes 6h 00m
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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Frequently asked questions about flying from Chicago to St. John's

  • 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 6h 00m 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.

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

  • How do I get Price Alerts for flights from Chicago to St. John's?

    Price Alerts will notify you by email when the price for flights to St. John's from Chicago decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

  • How can I save money on flights from Chicago to St. John's with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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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