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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

What airlines fly to Chicago O'Hare Intl Airport?

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport according to our data. Air Canada is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

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

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

How often are flights from Toronto to Chicago delayed?

Historically, on average around 10% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 143 minutes.

What is the cheapest airline that flies from Toronto Pearson Intl to Chicago O'Hare Intl?

United Airlines is the most popular carrier operating from Toronto Pearson Intl to Chicago O'Hare Intl

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

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

How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

As of December 2025, there are 4 operators available to choose from for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The necessary travel and health documents for your Chicago O'Hare Intl 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.

$118 Cheap Flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in 2025/26

Q: How many flights depart from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport on average per week?

219 flights are operational weekly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport as of December 2025. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.

Q: How many flights depart from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport on average per day?

As of December 2025, there are 31 flights per day flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. The most common time of day flights depart is 6:00AM, with 45% of flights taking off at noon.

Q: What is the typical price of a round-trip flight between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport?

Prices are currently low for flights on this route. Typical prices usually range from $271 to $429. The lowest price recently found on this route was $180.

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Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:45 pm - 7:45 pm

YYZ

ORD

2h 00mnonstop

8:40 pm - 11:19 pm

ORD

YYZ

1h 39mnonstop

$180Air Canada

Sat, Jan 24 - Sun, Feb 1

5:30 pm - 6:50 pm

YYZ

ORD

2h 20mnonstop

7:10 am - 9:58 am

ORD

YYZ

1h 48mnonstop

$186United Airlines

Thu, Feb 5 - Sun, Feb 8

10:00 am - 2:55 pm

YYZ

ORD

5h 55m1 stop

8:00 am - 10:40 am

ORD

YYZ

1h 40mnonstop

$188Air Canada

Sat, Jan 24 - Sun, Feb 1

9:00 am - 2:55 pm

YYZ

ORD

6h 55m1 stop

8:00 am - 10:40 am

ORD

YYZ

1h 40mnonstop

$190Air Canada

Thu, Jan 29 - Thu, Feb 5

11:35 am - 12:30 pm

YYZ

ORD

1h 55mnonstop

10:10 am - 3:50 pm

ORD

YYZ

4h 40m1 stop

$191American Airlines

Thu, Feb 5 - Sun, Feb 8

2:00 pm - 8:10 pm

YYZ

ORD

7h 10m1 stop

2:00 pm - 4:39 pm

ORD

YYZ

1h 39mnonstop

$192Air Canada

Wed, Jan 28 - Wed, Feb 4

9:00 am - 2:55 pm

YYZ

ORD

6h 55m1 stop

8:00 am - 10:40 am

ORD

YYZ

1h 40mnonstop

$193Air Canada

Thu, Jan 29 - Thu, Feb 5

4:50 pm - 5:48 pm

YYZ

ORD

1h 58mnonstop

8:40 pm - 11:19 pm

ORD

YYZ

1h 39mnonstop

$194Air Canada

Fri, Jan 30 - Fri, Feb 6

11:38 am - 12:33 pm

YYZ

ORD

1h 55mnonstop

5:35 am - 11:52 am

ORD

YYZ

5h 17m1 stop

$195American Airlines

Thu, Feb 12 - Mon, Feb 16

4:50 pm - 5:48 pm

YYZ

ORD

1h 58mnonstop

8:00 am - 10:40 am

ORD

YYZ

1h 40mnonstop

$196Air Canada

Thu, Jan 29 - Thu, Feb 5

United Airlines flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Our best United Airlines deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets

United Airlines

Feb 5

YYZ5:30 pmToronto Pearson Intl

2h 20m

ORD6:50 pmChicago O'Hare Intl

Feb 8

ORD7:10 amChicago O'Hare Intl

1h 48m

YYZ9:58 amToronto Pearson Intl

$186

Find similar

United Airlines

Dec 31

YYZ9:00 pmToronto Pearson Intl

2h 05m

ORD10:05 pmChicago O'Hare Intl

Jan 31

ORD7:10 amChicago O'Hare Intl

1h 48m

YYZ9:58 amToronto Pearson Intl

$204

Find similar

United Airlines

Feb 24

YYZ3:30 pmToronto Pearson Intl

2h 09m

ORD4:39 pmChicago O'Hare Intl

Feb 27

ORD2:30 pmChicago O'Hare Intl

8h 16m

1 stop

YYZ11:46 pmToronto Pearson Intl

$209

Find similar

Delta flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Our best Delta deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets

Delta

Feb 5

YYZ6:00 amToronto Pearson Intl

4h 41m

1 stop

ORD9:41 amChicago O'Hare Intl

Feb 8

ORD1:58 pmChicago O'Hare Intl

4h 10m

1 stop

YYZ7:08 pmToronto Pearson Intl

$213

Find similar

Delta

Jan 29

YYZ6:00 amToronto Pearson Intl

8h 18m

1 stop

ORD1:18 pmChicago O'Hare Intl

Feb 5

ORD10:29 amChicago O'Hare Intl

5h 54m

1 stop

YYZ5:23 pmToronto Pearson Intl

$225

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 1/24

6:45 pm-7:45 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sun 2/1

8:40 pm-11:19 pm

Nonstop1h 39m

$180

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/5

5:30 pm-6:50 pm

Nonstop2h 20m

Chicago O'Hare Intl

Sun 2/8

7:10 am-9:58 am

Nonstop1h 48m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 1/24

10:00 am-2:55 pm

1 stop5h 55m

Chicago O'Hare Intl

Sun 2/1

8:00 am-10:40 am

Nonstop1h 40m

$188

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/29

9:00 am-2:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Thu 2/5

8:00 am-10:40 am

Nonstop1h 40m

$190

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/5

11:35 am-12:30 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 2/8

10:10 am-3:50 pm

1 stop4h 40m

$191

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/28

2:00 pm-8:10 pm

1 stop7h 10m

Chicago O'Hare Intl

Wed 2/4

2:00 pm-4:39 pm

Nonstop1h 39m

$192

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/29

9:00 am-2:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Thu 2/5

8:00 am-10:40 am

Nonstop1h 40m

$193

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 1/30

4:50 pm-5:48 pm

Nonstop1h 58m

Chicago O'Hare Intl

Fri 2/6

8:40 pm-11:19 pm

Nonstop1h 39m

$194

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/12

11:38 am-12:33 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 2/16

5:35 am-11:52 am

1 stop5h 17m

$195

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/29

4:50 pm-5:48 pm

Nonstop1h 58m

Chicago O'Hare Intl

Thu 2/5

8:00 am-10:40 am

Nonstop1h 40m

$196

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 Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

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 typical price of a round-trip flight between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto Pearson Intl Airport averaging around $253.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $458. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto Pearson Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $739.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $392 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $650. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Toronto Pearson Intl to Chicago O'Hare Intl flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $291 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport for as low as $195 on momondo.

What cabin class options are available on Toronto Pearson Intl to Chicago O'Hare Intl flights?

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

How have Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight prices changed over time?

As of December 2025, prices for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights are approximately 2% cheaper when compared to flights at the same time last year.

When to book flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

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

Estimated round-trip price

Cheap Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (YYZ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Best Price Found	$262
Fastest flight time	1h 55m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in the past 72 hours is $262. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $365.

The fastest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport takes 1h 55m

Direct flights go from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport every day.

Search flight deals

How far is Toronto Pearson Intl to Chicago O'Hare Intl by plane?
Chicago O'Hare Intl is 435.5 mi away from Toronto Pearson Intl. Flights usually cover this in 1h 55m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Prices for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport refresh daily.
How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
As of December 2025, there are 4 operators available to choose from for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl 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.
What is the most popular plane model from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport, the leading plane model is Embraer 195 E2, making up 11.58% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 11.57%, Embraer 175 (Enhanced Winglets) with 10.84%, and Boeing 737-800 with 9.33%.
What is the most popular airline from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is Air Canada (48% of total bookings). The next most popular airlines are United Airlines (30%), American Airlines (19%), and Porter Airlines (3%).

Best airlines flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $150	Free Cancellation	Rating 7.1 10,527 reviews	Search Air Canada flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 9,094 reviews	Search United Airlines flights
Porter Airlines	PriceFrom $180	Free Cancellation	Rating 8.0 399 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $195	Free Cancellation	Rating 7.2 11,048 reviews	Search American Airlines flights

Porter Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Across 16 Porter Airlines flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport this week, the average price was $423, with the best Porter Airlines deals starting from $180 round-trip. 399 users have rated Porter Airlines on momondo, with an average score of 8.0/10.
United Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
The best United Airlines deal for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $165, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $281 round-trip. United Airlines operates 52 flights out of Toronto Pearson Intl Airport into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 9,094 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

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

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

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

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

momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Toronto 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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Cheap flights from Toronto Pearson Intl Airport to Chicago from $118

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United Airlines flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Our best United Airlines deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets

Delta flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Our best Delta deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets

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Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

What is the typical price of a round-trip flight between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto Pearson Intl Airport averaging around $253.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest Toronto Pearson Intl to Chicago O'Hare Intl flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

What cabin class options are available on Toronto Pearson Intl to Chicago O'Hare Intl flights?

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

How have Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight prices changed over time?

As of December 2025, prices for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights are approximately 2% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Toronto Pearson Intl to Chicago O'Hare Intl?

United Airlines is the most popular carrier operating from Toronto Pearson Intl to Chicago O'Hare Intl

What airlines fly to Chicago O'Hare Intl Airport?

How often are flights from Toronto to Chicago delayed?

Historically, on average around 10% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 143 minutes.

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

Generally, flights departing at night tend to experience fewer delays. Flights 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 which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

How many flights depart from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport on average per day?

As of December 2025, there are 31 flights per day flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. The most common time of day flights depart is 6:00AM, with 45% of flights taking off at noon.

How many flights depart from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport on average per week?

219 flights are operational weekly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport as of December 2025. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.

When to book flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Cheap Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (YYZ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Best Price Found

Fastest flight time

Direct flights

How far is Toronto Pearson Intl to Chicago O'Hare Intl by plane?

When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

What is the most popular plane model from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

What is the most popular airline from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

Best airlines flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport with momondo

Porter Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

United Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago O'Hare Intl Airport 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 Chicago

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Popular flights according to clicks in the last 7 days on momondo