What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

What is the cheapest airline that flies from Canada to Chicago?

WestJet, Porter Airlines, and United Airlines are the most popular carriers operating from Canada to Chicago

Which airlines fly to Chicago?

Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago from Canada according to our data. Air Canada is the first choice among our users, with 54% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which airline has the best punctuality record on Canada to Chicago flights?

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 7% of their flights experiencing any sort of delay.

How many flights depart from Canada to Chicago on average per week?

676 flights are operational weekly from Canada to Chicago as of January 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Toronto and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 1h 55m on average. Another popular route from Canada to Chicago is flying from Montreal to Chicago O'Hare Intl Airport, which will take roughly 2h 35m. Keep in mind that layovers or delays could extend your travel time.

How often are flights from Canada to Chicago delayed?

Historically, on average around 12% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 138 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

How many flights depart from Canada to Chicago on average per day?

The number of flights available between Canada and Chicago is 96 per day as of January 2026. The most frequent departure time is 6:00a.m., with 47% of daily flights leaving in the afternoon.

When did momondo last update prices for flights from Canada to Chicago?

Prices for flights from Canada to Chicago were last updated today.

How many operators does momondo search for flights from Canada to Chicago?

The number of operators available for flights from Canada to Chicago is 7 as of January 2026.

How old do you have to be to fly from Canada to Chicago?

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 Canada to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago 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.

C$ 136 Cheap Flights from Canada to Chicago in 2026

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Find the cheapest flights from Canada to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

12:00 p.m. - 4:40 p.m.

YYC

ORD

3h 40mdirect

5:30 p.m. - 8:25 p.m.

ORD

YYC

3h 55mdirect

C$ 247WestJet

lun., 27 abr. - vie., 1 may.

9:25 a.m. - 11:18 a.m.

YUL

ORD

2h 53mdirect

12:50 p.m. - 4:05 p.m.

ORD

YUL

2h 15mdirect

C$ 247Air Canada

jue., 26 mar. - lun., 30 mar.

6:30 a.m. - 9:40 a.m.

YUL

MDW

4h 10m

1 stop

10:25 a.m. - 5:15 p.m.

MDW

YUL

5h 50m

1 stop

C$ 248Porter Airlines

vie., 1 may. - lun., 4 may.

4:45 p.m. - 6:45 p.m.

YUL

ORD

3h 00mdirect

8:50 a.m. - 3:16 p.m.

ORD

YUL

5h 26m

1 stop

C$ 251United Airlines

jue., 19 feb. - sáb., 21 feb.

6:30 a.m. - 9:40 a.m.

YUL

MDW

4h 10m

1 stop

10:25 a.m. - 5:15 p.m.

MDW

YUL

5h 50m

1 stop

C$ 253Porter Airlines

jue., 4 jun. - dom., 7 jun.

7:00 a.m. - 8:00 a.m.

YYZ

ORD

2h 00mdirect

9:15 p.m. - 11:59 p.m.

ORD

YYZ

1h 44mdirect

C$ 257United Airlines

vie., 19 jun. - dom., 21 jun.

9:20 a.m. - 10:10 a.m.

YTZ

MDW

1h 50mdirect

11:05 a.m. - 1:47 p.m.

MDW

YTZ

1h 42mdirect

C$ 274Air Transat

jue., 19 feb. - lun., 23 feb.

7:30 a.m. - 1:57 p.m.

YUL

ORD

7h 27m

1 stop

6:40 a.m. - 3:22 p.m.

ORD

YUL

7h 42m

1 stop

C$ 284American Airlines

mié., 18 feb. - sáb., 21 feb.

9:15 a.m. - 10:05 a.m.

YTZ

MDW

1h 50mdirect

4:15 p.m. - 6:57 p.m.

MDW

YTZ

1h 42mdirect

C$ 284Air Transat

lun., 20 abr. - jue., 23 abr.

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

YYC

ORD

3h 40mdirect

5:00 a.m. - 11:44 a.m.

ORD

YYC

7h 44m

1 stop

C$ 316American Airlines

mar., 24 feb. - mar., 3 mar.

Air Canada flights from Canada to Chicago

Our best Air Canada deals on Canada to Chicago flight tickets

Air Canada

26 Mar

YUL9:25 a.m.Montreal Pierre Elliott Trudeau Intl

2h 53m

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

30 Mar

ORD12:50 p.m.Chicago O'Hare Intl

2h 15m

YUL4:05 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 247

Air Canada

19 Feb

YUL6:25 p.m.Montreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:10 p.m.Chicago O'Hare Intl

21 Feb

ORD7:15 a.m.Chicago O'Hare Intl

2h 05m

YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 250

Air Canada

11 Jun

YUL8:15 a.m.Montreal Pierre Elliott Trudeau Intl

2h 38m

ORD9:53 a.m.Chicago O'Hare Intl

14 Jun

ORD8:45 a.m.Chicago O'Hare Intl

2h 15m

YUL12:00 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 258

Lufthansa flights from Canada to Chicago

Our best Lufthansa deals on Canada to Chicago flight tickets

Lufthansa

19 Feb

YYZ8:45 a.m.Toronto Pearson Intl

2h 05m

ORD9:50 a.m.Chicago O'Hare Intl

23 Feb

ORD6:28 p.m.Chicago O'Hare Intl

1h 53m

YYZ9:21 p.m.Toronto Pearson Intl

C$ 261

Lufthansa

19 Feb

YYZ9:00 p.m.Toronto Pearson Intl

2h 04m

ORD10:04 p.m.Chicago O'Hare Intl

23 Feb

ORD9:15 p.m.Chicago O'Hare Intl

1h 44m

YYZ11:59 p.m.Toronto Pearson Intl

C$ 267

Lufthansa

19 Feb

YYZ8:45 a.m.Toronto Pearson Intl

2h 05m

ORD9:50 a.m.Chicago O'Hare Intl

23 Feb

ORD6:28 p.m.Chicago O'Hare Intl

1h 53m

YYZ9:21 p.m.Toronto Pearson Intl

C$ 289

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 27/4

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

vie. 1/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 247

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

jue. 26/3

9:25 a.m.-11:18 a.m.

Nonstop2h 53m

Chicago O'Hare Intl

lun. 30/3

12:50 p.m.-4:05 p.m.

Nonstop2h 15m

C$ 247

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 1/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

lun. 4/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 248

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

jue. 19/2

4:45 p.m.-6:45 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

sáb. 21/2

8:50 a.m.-3:16 p.m.

1 stop5h 26m

C$ 251

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 4/6

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

dom. 7/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 253

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 19/6

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

dom. 21/6

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 19/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

lun. 23/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 274

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

mié. 18/2

7:30 a.m.-1:57 p.m.

1 stop7h 27m

Chicago O'Hare Intl

sáb. 21/2

6:40 a.m.-3:22 p.m.

1 stop7h 42m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 20/4

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

jue. 23/4

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 284

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mar. 24/2

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

Nonstop3h 40m

Chicago O'Hare Intl

mar. 3/3

5:00 a.m.-11:44 a.m.

1 stop7h 44m

C$ 316

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Canada 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

Delays

Other information

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 305.

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$ 573. 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$ 988. 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 evening is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 634. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,089 per ticket.

What is the cheapest Canada to Chicago flight route?

Fly from Calgary to Chicago O'Hare Intl for the best Canada - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 389 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as C$ 265 on momondo.

What cabin class options are available on Canada to Chicago flights?

There are 4 cabin classes available to choose from on Canada to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Canada to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a Canada to Chicago flight.

Cheap Canada to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago

Best price found	C$ 186
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Canada in the past 72 hours is C$ 186. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 261.

The fastest flight from Canada to Chicago takes 1h 50m

Direct flights go from Canada to Chicago every day.

There are 3 airports in Chicago. From Canada there are direct flights to Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Canada to Chicago?
Prices for flights from Canada to Chicago were last updated today.
How many operators does momondo search for flights from Canada to Chicago?
The number of operators available for flights from Canada to Chicago is 7 as of January 2026.
How old do you have to be to fly from Canada to Chicago?
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 Canada to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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.
What is the most popular plane model from Canada to Chicago?
Based on momondo bookings for flights between Canada and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 15.00% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 11.36%, Embraer 170 with 10.15%, and Embraer 175 with 8.00%.

Best airlines flying from Canada to Chicago

Compare and see reviews for airlines that fly from Canada to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 111	Free Cancellation	Rating 7.9 412 reviews	Search Porter Airlines flights
Delta	PriceFrom C$ 144	Free Cancellation	Rating 7.9 8,127 reviews	Search Delta flights
Air Canada	PriceFrom C$ 146	Free Cancellation	Rating 7.1 10,667 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 168	Free Cancellation	Rating 7.2 11,206 reviews	Search American Airlines flights
WestJet	PriceFrom C$ 172	Free Cancellation	Rating 7.2 3,253 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 175	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom C$ 380	Free Cancellation	Rating 8.0 11,808 reviews	Search Alaska Airlines flights

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Canada to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Canada to Chicago . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Canada to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.

How can momondo help me find flights from Canada to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Canada to Chicago.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Canada and alert you when they change.

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.

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sáb. 28/2

sáb. 7/3

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Popular Cities in the United States

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Cheap flights from Canada to Chicago from C$ 134

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Canada to Chicago departing on 26/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

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Price Alerts

Price Alerts

Find the cheapest flights from Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

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Air Canada flights from Canada to Chicago

Our best Air Canada deals on Canada to Chicago flight tickets

Lufthansa flights from Canada to Chicago

Our best Lufthansa deals on Canada to Chicago flight tickets

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Use the filters below to find and compare flights from Canada to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Canada to Chicago

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 305.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Canada to Chicago flight route?

Fly from Calgary to Chicago O'Hare Intl for the best Canada - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Canada to Chicago flights?

There are 4 cabin classes available to choose from on Canada to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Canada to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a Canada to Chicago flight.

What is the cheapest airline that flies from Canada to Chicago?

WestJet, Porter Airlines, and United Airlines are the most popular carriers operating from Canada to Chicago

Which airlines fly to Chicago?

How often are flights from Canada to Chicago delayed?

Historically, on average around 12% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 138 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 7% of their flights experiencing any sort of delay.

How many flights depart from Canada to Chicago on average per day?

The number of flights available between Canada and Chicago is 96 per day as of January 2026. The most frequent departure time is 6:00a.m., with 47% of daily flights leaving in the afternoon.

How many flights depart from Canada to Chicago on average per week?

676 flights are operational weekly from Canada to Chicago as of January 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Canada to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago

Best price found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Canada to Chicago?

How many operators does momondo search for flights from Canada to Chicago?

How old do you have to be to fly from Canada to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Canada to Chicago?

Best airlines flying from Canada to Chicago

Compare and see reviews for airlines that fly from Canada to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Canada to Chicago?

Can I find flights from Canada to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Canada to Chicago?

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

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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