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

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

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 week?

656 flights are operational weekly from Canada to Chicago as of January 2026. The most popular departure day for this route is Thu, 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.

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.

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.

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.

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

The number of flights available between Canada and Chicago is 93 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 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.

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$ 141 Cheap Flights from Canada to Chicago in 2026

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

9:00 a.m. - 1:35 p.m.

YYC

ORD

3h 35mdirect

2:20 p.m. - 5:15 p.m.

ORD

YYC

3h 55mdirect

C$ 212WestJet

Fri, 27 Feb - Fri, 6 Mar

9:00 a.m. - 1:35 p.m.

YYC

ORD

3h 35mdirect

2:20 p.m. - 5:15 p.m.

ORD

YYC

3h 55mdirect

C$ 228WestJet

Fri, 6 Mar - Mon, 9 Mar

6:45 a.m. - 10:10 a.m.

YUL

MDW

4h 25m

1 stop

11:05 a.m. - 5:45 p.m.

MDW

YUL

5h 40m

1 stop

C$ 252Porter Airlines

Thu, 19 Feb - Thu, 26 Feb

6:00 a.m. - 8:05 a.m.

YUL

ORD

3h 05mdirect

7:10 a.m. - 1:28 p.m.

ORD

YUL

5h 18m

1 stop

C$ 253United Airlines

Wed, 11 Feb - Tue, 17 Feb

8:00 a.m. - 5:48 p.m.

YYC

ORD

8h 48m

1 stop

2:00 p.m. - 8:44 p.m.

ORD

YYC

7h 44m

1 stop

C$ 257Air Canada

Tue, 24 Feb - Sat, 28 Feb

6:45 a.m. - 10:10 a.m.

YUL

MDW

4h 25m

1 stop

11:05 a.m. - 6:45 p.m.

MDW

YUL

6h 40m

1 stop

C$ 259Porter Airlines

Thu, 19 Feb - Fri, 20 Feb

11:00 a.m. - 12:08 p.m.

YYZ

ORD

2h 08mdirect

6:28 p.m. - 9:21 p.m.

ORD

YYZ

1h 53mdirect

C$ 261United Airlines

Tue, 10 Feb - Tue, 17 Feb

3:45 p.m. - 5:44 p.m.

YUL

ORD

2h 59mdirect

6:48 p.m. - 3:22 p.m.

ORD

YUL

19h 34m

1 stop

C$ 261American Airlines

Thu, 12 Feb - Fri, 20 Feb

12:05 p.m. - 1:01 p.m.

YYZ

ORD

1h 56mdirect

2:00 p.m. - 4:39 p.m.

ORD

YYZ

1h 39mdirect

C$ 263Air Canada

Mon, 2 Mar - Tue, 24 Mar

1:10 p.m. - 2:10 p.m.

YYZ

ORD

2h 00mdirect

5:00 a.m. - 11:13 a.m.

ORD

YYZ

5h 13m

1 stop

C$ 275American Airlines

Wed, 25 Feb - Fri, 27 Feb

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

United Airlines

11 Feb

YUL6:00 a.m.Montreal Pierre Elliott Trudeau Intl

3h 05m

ORD8:05 a.m.Chicago O'Hare Intl

17 Feb

ORD7:10 a.m.Chicago O'Hare Intl

5h 18m

1 stop

YUL1:28 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 253

United Airlines

10 Feb

YYZ11:00 a.m.Toronto Pearson Intl

2h 08m

ORD12:08 p.m.Chicago O'Hare Intl

17 Feb

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

1h 53m

YYZ9:21 p.m.Toronto Pearson Intl

C$ 261

United Airlines

11 Feb

YUL2:13 p.m.Montreal Pierre Elliott Trudeau Intl

5h 24m

1 stop

ORD6:37 p.m.Chicago O'Hare Intl

23 Feb

ORD8:50 a.m.Chicago O'Hare Intl

5h 26m

1 stop

YUL3:16 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 275

Delta flights from Canada to Chicago

Our best Delta deals on Canada to Chicago flight tickets

Delta

12 Feb

YYZ6:00 a.m.Toronto Pearson Intl

8h 29m

1 stop

ORD1:29 p.m.Chicago O'Hare Intl

14 Feb

ORD6:30 a.m.Chicago O'Hare Intl

8h 40m

1 stop

YYZ4:10 p.m.Toronto Pearson Intl

C$ 296

Delta

2 Mar

YYZ7:45 a.m.Toronto Pearson Intl

6h 35m

1 stop

ORD1:20 p.m.Chicago O'Hare Intl

6 Mar

ORD5:37 p.m.Chicago O'Hare Intl

4h 03m

1 stop

YYZ10:40 p.m.Toronto Pearson Intl

C$ 297

Delta

17 Feb

YUL6:00 p.m.Montreal Pierre Elliott Trudeau Intl

6h 56m

1 stop

ORD11:56 p.m.Chicago O'Hare Intl

22 Feb

ORD6:15 a.m.Chicago O'Hare Intl

6h 25m

1 stop

YUL1:40 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 299

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 27/2

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 212

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 6/3

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 228

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/2

6:45 a.m.-10:10 a.m.

1 stop4h 25m

Chicago Midway

Thu 26/2

11:05 a.m.-5:45 p.m.

1 stop5h 40m

C$ 252

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 11/2

6:00 a.m.-8:05 a.m.

Nonstop3h 05m

Chicago O'Hare Intl

Tue 17/2

7:10 a.m.-1:28 p.m.

1 stop5h 18m

C$ 253

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 24/2

8:00 a.m.-5:48 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Sat 28/2

2:00 p.m.-8:44 p.m.

1 stop7h 44m

C$ 257

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/2

6:45 a.m.-10:10 a.m.

1 stop4h 25m

Chicago Midway

Fri 20/2

11:05 a.m.-6:45 p.m.

1 stop6h 40m

C$ 259

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/2

11:00 a.m.-12:08 p.m.

Nonstop2h 08m

Chicago O'Hare Intl

Tue 17/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 261

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 12/2

3:45 p.m.-5:44 p.m.

Nonstop2h 59m

Chicago O'Hare Intl

Fri 20/2

6:48 p.m.-3:22 p.m.

1 stop19h 34m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 2/3

12:05 p.m.-1:01 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Tue 24/3

2:00 p.m.-4:39 p.m.

Nonstop1h 39m

C$ 263

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 25/2

1:10 p.m.-2:10 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Fri 27/2

5:00 a.m.-11:13 a.m.

1 stop5h 13m

C$ 275

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$ 311.

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$ 582. 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$ 1,016. 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$ 646. 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$ 396 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$ 270 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$ 196
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$ 196. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 283.

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 14.13% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 10.31%, Embraer 170 with 9.38%, and Airbus A220-300 with 8.43%.

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
Delta	PriceFrom C$ 146	Free Cancellation	Rating 7.9 8,087 reviews	Search Delta flights
Air Canada	PriceFrom C$ 149	Free Cancellation	Rating 7.1 10,646 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 171	Free Cancellation	Rating 7.2 11,173 reviews	Search American Airlines flights
WestJet	PriceFrom C$ 175	Free Cancellation	Rating 7.2 3,246 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 179	Free Cancellation	Rating 7.4 9,190 reviews	Search United Airlines flights
Porter Airlines	PriceFrom C$ 189	Free Cancellation	Rating 7.9 412 reviews	Search Porter Airlines flights
Alaska Airlines	PriceFrom C$ 387	Free Cancellation	Rating 8.0 11,775 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Sat 21/2

Sat 28/2

Email me momondo's favourite deals

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

Chicago Midway Airport

Chicago O'Hare Intl Airport

Popular Cities in the United States

Flights to Fort Lauderdalefrom C$ 156

Flights to Orlandofrom C$ 122

Flights to New Yorkfrom C$ 252

Flights to Las Vegasfrom C$ 133

Flights to Los Angelesfrom C$ 147

Flights to Miamifrom C$ 328

Flights to San Franciscofrom C$ 163

Flights to Honolulufrom C$ 372

Flights to Phoenixfrom C$ 188

Flights to Tampafrom C$ 223

Flights to Houstonfrom C$ 253

Flights to Seattlefrom C$ 218

Cheap flights from Canada to Chicago from C$ 141

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 9/3. 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

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Recent one-way flight deals from Canada to Chicago

Recent last minute flight deals from Canada to Chicago

Recent direct flight deals from Canada to Chicago

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

Delta flights from Canada to Chicago

Our best Delta deals on Canada to Chicago flight tickets

momondo Fare Finder

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$ 311.

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?

Porter Airlines, Air Canada, 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 93 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?

656 flights are operational weekly from Canada to Chicago as of January 2026. The most popular departure day for this route is Thu, 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