Find Cheap Flights from Toronto Pearson Intl to Chicago (YYZ - CHI)

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Good to Know

Low Season:
May
Best time to beat the crowds
3%
expected price decrease
High Season:
November
Most popular time to fly
7%
expected price increase
Average price:
C$ 410
(avg. price over the last 2 weeks)
Good Deal:
C$ 287
or less (round trip)

When to Book Flights from Toronto Pearson Intl to Chicago

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for C$ 286 or less.
The cheapest flight from Toronto Pearson Intl to Chicago was found, on average, 81 days before departure.
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be October, November and December. The cheapest month to fly is May.
Morning departure is around 38% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Toronto Pearson Intl to Chicago Flights

How long does a flight from Toronto Pearson Intl to Chicago take?
An average nonstop flight takes 1h 47m, covering a distance of 684 km.
How many flights are there between Toronto Pearson Intl and Chicago?
There are 489 (nonstop) flights between Toronto Pearson Intl and Chicago per week, averaging 71 per day.
Which airlines provide the cheapest flights from Toronto Pearson Intl to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Delta (C$ 262) and Multiple Airlines (C$ 272)
Do I need a passport to fly between Toronto Pearson Intl and Chicago?
Yes.
Which airlines fly most frequently between Toronto Pearson Intl and Chicago?
United (12 times daily), Air Canada (11 times daily), American Airlines (7 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from Toronto Pearson Intl to Chicago?
For Toronto Pearson Intl to Chicago, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago back to Toronto Pearson Intl, the best deals are generally found on Thursday, with Tuesday being the most expensive.

Book cheap flights from Toronto Pearson Intl to Chicago (round-trip)

Airports
Origin
Toronto
C$ 262
only
C$ 262
Destination
Chicago
C$ 262
only
C$ 262
C$ 262
only
C$ 262
Mon, 5 Feb
YYZ
ORD
5h 02m
Wed, 7 Feb
ORD
YYZ
6h 46m
C$ 262
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

Thu, 1 Mar
YYZ
ORD
1h 57m
Tue, 20 Mar
ORD
YYZ
1h 31m
C$ 272
Trip: 19 days
Overall 0.0 Poor
Based on 0 reviews
Tue, 6 Feb
YYZ
ORD
5h 55m
Wed, 14 Feb
ORD
YYZ
5h 10m
C$ 262
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

DEN
SLC
Excellent 10.0

Delta is great

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

Thu, 12 Apr
YYZ
ORD
1h 51m
Sun, 15 Apr
ORD
YYZ
1h 33m
C$ 272
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 7 Feb
YYZ
ORD
5h 55m
Wed, 14 Feb
ORD
YYZ
5h 10m
C$ 262
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Excellent 10.0

Delta is great

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

JFK
SJU
Excellent 10.0

Giid free sandwixh. Very good entertainment system. Good seats.

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

Mon, 12 Feb
YYZ
ORD
1h 57m
Fri, 16 Feb
ORD
YYZ
1h 31m
C$ 273
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 8 Feb
YYZ
ORD
5h 55m
Wed, 14 Feb
ORD
YYZ
6h 56m
C$ 262
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
SJC
Excellent 10.0

It’s was the best flight in my life

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

Fri, 23 Feb
YYZ
ORD
1h 59m
Mon, 26 Feb
ORD
YYZ
1h 31m
C$ 273
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 9 Feb
YYZ
ORD
6h 27m
Wed, 14 Feb
ORD
YYZ
5h 10m
C$ 262
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

DEN
SLC
Excellent 10.0

Delta is great

JFK
SJU
Excellent 10.0

Giid free sandwixh. Very good entertainment system. Good seats.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

Sat, 24 Feb
YYZ
ORD
1h 57m
Mon, 26 Feb
ORD
YYZ
1h 31m
C$ 273
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Mon, 12 Feb
YYZ
ORD
5h 36m
Wed, 21 Feb
ORD
YYZ
6h 50m
C$ 262
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

Mon, 5 Mar
YYZ
ORD
1h 57m
Wed, 21 Mar
ORD
YYZ
1h 31m
C$ 273
Trip: 16 days
Overall 0.0 Poor
Based on 0 reviews
Tue, 13 Feb
YYZ
ORD
6h 27m
Tue, 27 Feb
ORD
YYZ
6h 54m
C$ 262
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
SJC
Excellent 10.0

It’s was the best flight in my life

JFK
SJU
Excellent 10.0

Giid free sandwixh. Very good entertainment system. Good seats.

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

Fri, 16 Mar
YYZ
ORD
1h 57m
Sun, 25 Mar
ORD
YYZ
1h 31m
C$ 273
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 14 Feb
YYZ
MDW
4h 56m
Wed, 21 Feb
MDW
YYZ
4h 50m
C$ 262
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

JFK
SJU
Excellent 10.0

Giid free sandwixh. Very good entertainment system. Good seats.

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

Thu, 29 Mar
YYZ
ORD
1h 57m
Sun, 1 Apr
ORD
YYZ
1h 33m
C$ 273
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 21 Feb
YYZ
ORD
7h 01m
Tue, 27 Feb
ORD
YYZ
6h 54m
C$ 262
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
HKG
SEA
Good 6.0

The flight was on time and the arrival was early

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

Thu, 24 May
YYZ
ORD
1h 47m
Tue, 29 May
ORD
YYZ
1h 31m
C$ 280
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, 6 Mar
YYZ
ORD
6h 50m
Mon, 12 Mar
ORD
YYZ
5h 20m
C$ 262
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
SJU
Excellent 10.0

Giid free sandwixh. Very good entertainment system. Good seats.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

Thu, 21 Jun
YYZ
ORD
1h 47m
Sat, 23 Jun
ORD
YYZ
1h 31m
C$ 280
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Show more results

Toronto Pearson Intl to Chicago Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Chicago
Flights Depart from Toronto Pearson Intl
Flight Price C$ 262
Distance 684 km
Airlines Delta
*
Prices are per person, are for e–tickets and include all taxes & fees in CAD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

^
The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.