What airlines fly to Toronto?

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Toronto from Chicago according to our data. Air Canada is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Toronto. Keep in mind that there are 4 different airlines that fly to Toronto on a routine basis, so you have a few additional options to choose from.

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

The number of flights available between Chicago and Toronto is 47 per day as of August 2025. The most frequent departure time is 8:00PM, with 40% of daily flights leaving at noon.

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

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

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

331 flights are operational weekly from Chicago to Toronto as of August 2025. The most popular departure day for this route is Tue, with 20% of flights per week taking off on this day.

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

Prices for flights from Chicago to Toronto refresh daily.

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

There are 4 operators available for flights from Chicago to Toronto as of August 2025.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Toronto.

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

The travel and health documents required for your trip to Toronto 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 Toronto. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$55 Cheap Flights from Chicago to Toronto in 2025

Q: What is the typical price of a round-trip flight between Chicago and Toronto?

Prices are currently low for flights on this route. Typical prices usually range from $202 to $330. The lowest price recently found on this route was $167.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? 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 Chicago to Toronto

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

4:50 pm - 7:45 pmORD-YYZ

1h 55mnonstop

5:30 pm - 6:39 pmYYZ-ORD

2h 09mnonstop

$167United Airlines

Find Deal

Fri, Nov 7 - Mon, Nov 10

5:20 am - 2:59 pmORD-YYZ

8h 39m1 stop

6:29 pm - 7:29 pmYYZ-ORD

2h 00mnonstop

$173American Airlines

Find Deal

Sat, Oct 11 - Sat, Oct 11

2:39 pm - 11:46 pmORD-YYZ

8h 07m1 stop

5:30 pm - 6:39 pmYYZ-ORD

2h 09mnonstop

$177United Airlines

Find Deal

Fri, Nov 7 - Mon, Nov 10

10:00 am - 12:39 pmORD-YYZ

1h 39mnonstop

2:15 pm - 3:10 pmYYZ-ORD

1h 55mnonstop

$183Air Canada

Find Deal

Thu, Oct 30 - Sun, Nov 2

8:25 pm - 11:08 pmORD-YYZ

1h 43mnonstop

12:05 pm - 1:01 pmYYZ-ORD

1h 56mnonstop

$184Air Canada

Find Deal

Fri, Oct 3 - Mon, Nov 3

9:35 am - 12:17 pmMDW-YTZ

1h 42mnonstop

7:50 am - 8:39 amYTZ-MDW

1h 49mnonstop

$188Porter Airlines

Find Deal

Sat, Sep 6 - Sun, Sep 14

9:35 am - 12:17 pmMDW-YTZ

1h 42mnonstop

7:50 am - 8:39 amYTZ-MDW

1h 49mnonstop

$192Porter Airlines

Find Deal

Thu, Sep 4 - Sun, Sep 7

5:05 am - 2:05 pmORD-YYZ

8h 00m1 stop

6:30 am - 5:39 pmYYZ-ORD

12h 09m1 stop

$212

Find Deal

Tue, Sep 23 - Tue, Sep 30

5:05 am - 2:05 pmORD-YYZ

8h 00m1 stop

2:10 pm - 3:04 pmYYZ-ORD

1h 54mnonstop

$216

Find Deal

Thu, Sep 18 - Thu, Sep 25

9:39 am - 12:32 pmORD-YYZ

1h 53mnonstop

7:35 am - 10:39 pmYYZ-ORD

16h 04m1 stop

$229British Airways

Find Deal

Sat, Sep 6 - Sun, Sep 7

WestJet flights from Chicago to Toronto

Our best WestJet deals on Chicago to Toronto flight tickets

WestJet

Sep 3

ORD1:40 pmChicago O'Hare Intl

9h 51m

1 stop

YYZ12:31 amToronto Pearson Intl

Sep 11

YYZ8:00 amToronto Pearson Intl

9h 43m

1 stop

ORD4:43 pmChicago O'Hare Intl

$239

Find similar

WestJet

Oct 10

ORD5:30 pmChicago O'Hare Intl

30h 10m

1 stop

YHM12:40 amHamilton

Oct 13

YHM6:00 amHamilton

11h 43m

1 stop

ORD4:43 pmChicago O'Hare Intl

$243

Find similar

WestJet

Sep 26

ORD5:30 pmChicago O'Hare Intl

30h 10m

1 stop

YHM12:40 amHamilton

Sep 29

YHM6:00 amHamilton

11h 43m

1 stop

ORD4:43 pmChicago O'Hare Intl

$244

Find similar

Air Canada flights from Chicago to Toronto

Our best Air Canada deals on Chicago to Toronto flight tickets

Air Canada

Oct 30

ORD10:00 amChicago O'Hare Intl

1h 39m

YYZ12:39 pmToronto Pearson Intl

Nov 2

YYZ2:15 pmToronto Pearson Intl

1h 55m

ORD3:10 pmChicago O'Hare Intl

$183

Find similar

Air Canada

Oct 3

ORD8:25 pmChicago O'Hare Intl

1h 43m

YYZ11:08 pmToronto Pearson Intl

Nov 3

YYZ12:05 pmToronto Pearson Intl

1h 56m

ORD1:01 pmChicago O'Hare Intl

$184

Find similar

Air Canada

Oct 26

ORD3:55 pmChicago O'Hare Intl

1h 39m

YYZ6:34 pmToronto Pearson Intl

Oct 28

YYZ4:30 pmToronto Pearson Intl

1h 58m

ORD5:28 pmChicago O'Hare Intl

$198

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 11/7

4:50 pm-7:45 pm

Nonstop1h 55m

Toronto Pearson Intl

Mon 11/10

5:30 pm-6:39 pm

Nonstop2h 09m

$167

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 10/11

5:20 am-2:59 pm

1 stop8h 39m

Toronto Pearson Intl

Sat 10/11

6:29 pm-7:29 pm

Nonstop2h 00m

$173

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 11/7

2:39 pm-11:46 pm

1 stop8h 07m

Toronto Pearson Intl

Mon 11/10

5:30 pm-6:39 pm

Nonstop2h 09m

$177

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 10/30

10:00 am-12:39 pm

Nonstop1h 39m

Toronto Pearson Intl

Sun 11/2

2:15 pm-3:10 pm

Nonstop1h 55m

$183

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 10/3

8:25 pm-11:08 pm

Nonstop1h 43m

Toronto Pearson Intl

Mon 11/3

12:05 pm-1:01 pm

Nonstop1h 56m

$184

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 9/6

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/14

7:50 am-8:39 am

Nonstop1h 49m

$188

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/7

7:50 am-8:39 am

Nonstop1h 49m

$192

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 9/23

5:05 am-2:05 pm

1 stop8h 00m

Toronto Pearson Intl

Tue 9/30

6:30 am-5:39 pm

1 stop12h 09m

$212

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 9/18

5:05 am-2:05 pm

1 stop8h 00m

Toronto Pearson Intl

Thu 9/25

2:10 pm-3:04 pm

Nonstop1h 54m

$216

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 9/6

9:39 am-12:32 pm

Nonstop1h 53m

Toronto Pearson Intl

Sun 9/7

7:35 am-10:39 pm

1 stop16h 04m

$229

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 Chicago to Toronto

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

Other information

What is the typical price of a round-trip flight between Chicago and Toronto?

What is the cheapest month to fly to Toronto?

The month of June is, on average, the cheapest month to fly to Toronto from Chicago, with most prices found around $261. If you are unable to visit Toronto during the month of June, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $261.

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

On average, the least expensive day to fly to Toronto from Chicago is on a Friday. momondo users have found tickets for Friday departures for as low as $481. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Toronto is Sunday, with ticket prices averaging around $709.

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

In the morning is the cheapest time of day to fly from Chicago to Toronto when you can find flight prices for as low as $444. Flying to Toronto in the morning is an ideal time because this is during off-peak travel hours. Flights to Toronto are more costly in the afternoon, with an average ticket price of $715. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Toronto flight route?

Fly from Chicago Midway to Toronto Island for the best Chicago - Toronto flight prices

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

You are more likely to see cheaper flights to Toronto from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Toronto for around $312 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Toronto from Chicago for as low as $166 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Toronto 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 Chicago to Toronto flights?

No. A direct flight is the cheapest option for a flight between Chicago to Toronto.

How have Chicago to Toronto flight prices changed over time?

As of August 2025, prices for Chicago to Toronto flights are approximately 41% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Toronto

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Toronto according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Toronto (CHI to YTO) flight deals and tips

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

Best Price Found	$55
Fastest flight time	1h 39m
Direct flights	Every day
Airports in Toronto	2 airports

The best one-way flight to Toronto from Chicago in the past 72 hours is $55. The best round-trip flight deal from Chicago to Toronto found on momondo in the last 72 hours is $167.

The fastest flight from Chicago to Toronto takes 1h 39m

Direct flights go from Chicago to Toronto every day.

There are 2 airports near Toronto: Toronto Pearson Intl (YYZ), Toronto Island (YTZ)

Search flight deals

How far is Chicago to Toronto by plane?
A flight from Chicago to Toronto will travel around 435.3 mi. Typically, this will take 1h 39m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Toronto?
Prices for flights from Chicago to Toronto refresh daily.
How many operators does momondo search for flights from Chicago to Toronto?
There are 4 operators available for flights from Chicago to Toronto as of August 2025.
How old do you have to be to fly from Chicago to Toronto?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Toronto.
What documentation or ID do you need to fly to Toronto?
The travel and health documents required for your trip to Toronto 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 Toronto. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Toronto?
Based on momondo bookings for flights between Chicago and Toronto, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 20.82% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 18.83%, Embraer 175 with 12.70%, and Boeing 737-800 with 7.86%.
What is the most popular airline from Chicago to Toronto?
Based on momondo bookings for flights between Chicago and Toronto, the leading airline is Porter Airlines, making up 54% of the total bookings. Other popular airlines include United Airlines with 17%, Air Canada with 17%, and American Airlines with 10%.

Best airlines flying from Chicago to Toronto

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

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $120	Free Cancellation	Rating 7.1 9,883 reviews	Search Air Canada flights
United Airlines	PriceFrom $145	Free Cancellation	Rating 7.4 8,915 reviews	Search United Airlines flights
Porter Airlines	PriceFrom $187	Free Cancellation	Rating 8.0 321 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $201	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Porter Airlines Flights From Chicago to Toronto
Across 13 Porter Airlines flights from Chicago to Toronto this week, the average price was $273, with the best Porter Airlines deals starting from $187 round-trip. 321 users have rated Porter Airlines on momondo, with an average score of 8.0/10.
United Airlines Flights From Chicago to Toronto
$145 is the best United Airlines flight deal from Chicago to Toronto found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $314, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,915 user reviews) flies into Toronto from Chicago 77 times in an average week so prices can vary.

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Toronto from Chicago.

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

Yes. momondo allows you to filter the results for Chicago to Toronto flights to just show those with flexible booking policies.

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

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 Toronto from Chicago.

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

If you are not ready to book a flight from Chicago to Toronto now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Toronto and let you know when they change.

An easier way to manage your Toronto 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

Sun 8/10

Sun 8/17

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada

Cheap flights from Chicago to Toronto from $55

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 Toronto departing on 11/19. 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 and deals

Big names and 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 Chicago to Toronto

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

WestJet flights from Chicago to Toronto

Our best WestJet deals on Chicago to Toronto flight tickets

Air Canada flights from Chicago to Toronto

Our best Air Canada deals on Chicago to Toronto flight tickets

momondo Fare Finder

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

See travel insights to Toronto from

How to get the cheapest flight ticket from Chicago to Toronto

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 typical price of a round-trip flight between Chicago and Toronto?

What is the cheapest month to fly to Toronto?

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

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

What is the cheapest Chicago to Toronto flight route?

Fly from Chicago Midway to Toronto Island for the best Chicago - Toronto flight prices

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

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

There are 4 cabin classes available to choose from on Chicago to Toronto 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 Chicago to Toronto flights?

No. A direct flight is the cheapest option for a flight between Chicago to Toronto.

How have Chicago to Toronto flight prices changed over time?

As of August 2025, prices for Chicago to Toronto flights are approximately 41% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Toronto?

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

The number of flights available between Chicago and Toronto is 47 per day as of August 2025. The most frequent departure time is 8:00PM, with 40% of daily flights leaving at noon.

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

331 flights are operational weekly from Chicago to Toronto as of August 2025. The most popular departure day for this route is Tue, with 20% of flights per week taking off on this day.

When to book flights from Chicago to Toronto

Cheap Chicago to Toronto (CHI to YTO) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Toronto

How far is Chicago to Toronto by plane?

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

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

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

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

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

What is the most popular airline from Chicago to Toronto?

Best airlines flying from Chicago to Toronto

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

Porter Airlines Flights From Chicago to Toronto

United Airlines Flights From Chicago to Toronto

Why use momondo?

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

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

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

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

An easier way to manage your Toronto 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 Canada

Fly into one of these airports located in Toronto

Airports listed have a maximum distance of 52.0 mi from Toronto