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

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Mon 20/11
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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$ 434
(avg. price over the last 2 weeks)
Good Deal:
C$ 304
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

When looking for a cheap flight, consider that 25% of our users selected a flight on this route for C$ 304 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 14% 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 42m, covering a distance of 684 km.
How many flights are there between Toronto Pearson Intl and Chicago?
There are 758 (nonstop) flights between Toronto Pearson Intl and Chicago per week, averaging 111 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$ 263), American Airlines (C$ 264) and Multiple Airlines (C$ 267).
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?
Air Canada (24 times daily), United (22 times daily), Aer Lingus (10 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, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Toronto Pearson Intl, the best deals are generally found on Saturday, with Friday being the most expensive.

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

Airports
Origin
Toronto
C$ 263
only
C$ 263
Destination
Chicago
C$ 263
only
C$ 263
Sat, 9 Dec
YYZ
ORD
6h 33m
Wed, 13 Dec
ORD
YYZ
5h 02m
C$ 263
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13550 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAN
LAX
Good 7.0

No entertainment

ATL
HOU
Excellent 10.0

same

MSP
BWI
Excellent 10.0

I am 6’3” and have difficulty with leg room on planes. Staff help me out by moving my son and I to Comfort seating row.

LGA
ATL
Excellent 9.0

No meal service in first class.

JFK
ATL
Mediocre 2.0

We landed

No drinks served , could not leave our seats , 2 hr flight turned into 3 hrs

Sat, 9 Dec
YYZ
ORD
2h 03m
Sun, 10 Dec
ORD
YYZ
5h 05m
C$ 264
Trip: 2 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
BHM
ORD
Excellent 10.0

The flight was a quick 39 minutes from Chicago, the staff was friendly. Good flight.

It's snowing!

YYZ
ORD
Mediocre 3.6

You provided a room

It seems you could have given me some extra miles or a free flight for all rhe hassles ov missing flights both going to Toronto and the return trip as well as missing my luggage for two days on the return!!!!!

TPA
DFW
Excellent 8.0

Quiet clean bathroom good layover time

YYZ
ORD
Good 7.6

Staff seemed tired with some minor conflicts between them at Toronto gate

BDA
JFK
Excellent 10.0

Flight attendants were attentive and pleasant

No IFE, bug not a big deal I had my own.

Wed, 13 Dec
YYZ
ORD
1h 59m
Thu, 14 Dec
ORD
YYZ
1h 31m
C$ 267
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 25 May
YYZ
ORD
1h 42m
Mon, 28 May
ORD
YYZ
1h 43m
C$ 291
Trip: 4 days
6.0GoodShow reviews
Overall 6.0 Good
Based on 60 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
YYZ
ORD
Good 6.0

The service staff was very friendly when they told me they were out of every food item I wanted.

Lack of variety in snacks, foods and purchases on the plane.

YYZ
ORD
Okay 4.6

Ok

Cannot gauge if carry-on would fit into overhead No entertainment

YYZ
ORD
Okay 5.3

Flight was on time and short in duration

Seats rows were narrow with just enough leg room. Very confining and uncomfortable. Our row did not recline as we were in front of the exit row. Luckily, the person in front of me did not recline their seat back.

YYZ
ORD
Excellent 10.0

comfortable and on time

YYZ
ORD
Okay 4.0

I didn't like nothing

United needs to training your employees

Thu, 21 Dec
YYZ
ORD
1h 47m
Thu, 28 Dec
ORD
YYZ
1h 31m
C$ 324
Trip: 8 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 190 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYZ
ORD
Mediocre 2.0

At the gate, we were told our plane would leave soon. An hour later, they announced the flight was cancelled and we were briskly escorted out of the terminal, told to go through customs and pick up our luggage, which had never even made it on to the plane. They were not re-booking flights at the airport, and the phone lines went to a voice mail message telling us to call back in a few days. I was stranded in Toronto with no phone and no where to stay. It's a week later and I still have not heard anything from from, even though I've called and emailed and sent snail mail.

YYZ
ORD
Okay 4.0

55 minutes before flight, after getting boarding pass they refused to accept baggage. Had to overnight at my expense.

Entertainment system didn't work, but only at my seat, after rebooting from electrical problem.

YYZ
ORD
Okay 4.3

We landed on time.

Flight attendant asked if I needed headphones and I said yes,her reply : I need a credit card

YYZ
ORD
Good 6.3

I enjoyed the crew, the food and the entertainment. The crew did give us peanuts for our extra 5 hours on the plane.

We were 3 hours late for departure and took 2 extra hours in the air because of re-routing. The seats were abnormally stiff and went back so little that it was extremely hard to fall asleep during the 18 hours we were on board. The crew was unwillng to let us bring our instruments on board and thus, they cracked from the air pressure during the flight.

YYZ
ORD
Okay 5.2

I arrived at the gate and looked at my ticket to see "GTE" where the seat number usually is. I was informed upon arriving at the desk at the gate that that meant Air Canada has also decided to participate in the ridiculous practice of overbooking their flights and that even though I purchased my ticket roughly 8 weeks prior, there was a chance I might miss my flight to my friend's WEDDING. The lady who was working the desk was as unhelpful and dismissive as you could possibly imagine, refusing to look at me and giving me attitude for merely waiting in the area to see if anyone had missed the flight so I could get on. It was surreal; the only way I could describe her incomprehensible behavior would be to say it was as if her boss were right in front of her and she was trying her damnedest to get fired. It was one of those situations where you could tell this miserable, miserable person was enjoying the power trip she was on and doing everything in her power to make me feel helpless and angry. I made my flight, miraculously, but it was the worst customer service experience I have ever had in my life, airport or not.

Sun, 10 Dec
YYZ
ORD
6h 25m
Wed, 13 Dec
ORD
YYZ
4h 00m
C$ 263
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13550 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HOU
Excellent 10.0

same

MSP
BWI
Excellent 10.0

I am 6’3” and have difficulty with leg room on planes. Staff help me out by moving my son and I to Comfort seating row.

LAX
SLC
Mediocre 2.0

Coffee is terrible! Get some medium roast for coffee aficionados. Not everyone has the American taste in coffee for a dark roast.

JFK
ATL
Mediocre 2.0

We landed

No drinks served , could not leave our seats , 2 hr flight turned into 3 hrs

JFK
LHR
Excellent 8.0

I booked via Kayak using Virgin Atlantic shared out to Delta. Check was confusing as both airlines used different flight numbers. When I went to check in with Virgin Atlantic they told me to go to Delta. When I went to Delta they told me to go back to Virgin Atlantic. I wound up checking in with Virgin Atlantic. Everyone was very polite but check in was confusing. Everything else was wonderful. Cutomer service was great from beginning to end.

Check in.

Thu, 14 Dec
YYZ
ORD
2h 00m
Sun, 17 Dec
ORD
YYZ
1h 31m
C$ 282
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 9 Feb
YYZ
ORD
1h 57m
Sun, 18 Feb
ORD
YYZ
1h 40m
C$ 287
Trip: 10 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
HND
Good 6.3

served snacks without drinks or at least water

TPA
DFW
Excellent 8.0

Quiet clean bathroom good layover time

YYZ
ORD
Good 7.6

Staff seemed tired with some minor conflicts between them at Toronto gate

BDA
JFK
Excellent 10.0

Flight attendants were attentive and pleasant

No IFE, bug not a big deal I had my own.

JFK
GRU
Good 6.0

It got me there safely without delays.

Food isn't good. the connections can be offered in a much better and time efficient way but they were not. I had to change airports in NYC with a 7-hr layover while they could've flown me to JFK (there was available flights). Same thing with coming back, a long layover in Texas.

Mon, 11 Dec
YYZ
ORD
7h 40m
Wed, 20 Dec
ORD
YYZ
5h 02m
C$ 263
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13550 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
SLC
Mediocre 2.0

Coffee is terrible! Get some medium roast for coffee aficionados. Not everyone has the American taste in coffee for a dark roast.

ATL
PDX
Excellent 8.6

Great entertainment, comfortable seats.

Middle seat with zero chance to switch.

ATL
HOU
Excellent 10.0

same

LGA
ATL
Excellent 9.0

No meal service in first class.

HND
LAX
Mediocre 2.0

Nothing

I did not board this flight as the previous one from Tokyo was late by an hour. Delta did not do ANYTHING to help us pass immigration and customs the fastest possible way. They sent us with the luggage to another terminal and had no signs or attendants to tell us where we recheck the bags. In the end we were late for the flight but Delta did not care!!! They tried putting me on a flight to SLC with a connection! Overall, I am VERY unhappy with them! Zero stars is what they deserve.

Wed, 14 Mar
YYZ
ORD
1h 54m
Sun, 18 Mar
ORD
YYZ
1h 43m
C$ 298
Trip: 5 days
6.0GoodShow reviews
Overall 6.0 Good
Based on 60 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
YYZ
ORD
Mediocre 3.6

I like that we landed.

This box seems too small to fit it all in. It's United - underwhelmed as usual.

YYZ
ORD
Mediocre 2.0

They delayed my flight, so now I get back home really late. Thanks, United.

YYZ
ORD
Excellent 10.0

Fantastic service. Much obliged for everything

YYZ
ORD
Mediocre 2.0

My complaint with United is twofold: extremely poor customer service and airport experience. First, the plane was delayed Then cancelled took customer service 50 minuets to rebooked on a new flight to sfo instead Sjc which is far away from my house & I paid for CAB!!

YYZ
ORD
Okay 4.0

I didn't like nothing

United needs to training your employees

Fri, 15 Dec
YYZ
ORD
2h 00m
Fri, 29 Dec
ORD
YYZ
1h 31m
C$ 282
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 14 Feb
YYZ
ORD
1h 57m
Sun, 18 Feb
ORD
YYZ
1h 40m
C$ 287
Trip: 5 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
YYZ
ORD
Good 7.6

Staff seemed tired with some minor conflicts between them at Toronto gate

LAX
HND
Good 6.3

served snacks without drinks or at least water

BDA
JFK
Excellent 10.0

Flight attendants were attentive and pleasant

No IFE, bug not a big deal I had my own.

LAX
HKG
Okay 4.0

Nothing

It wasn't Cathy Pacific operation.

ORD
MLI
Good 7.3

All great

Food and entertainment not applicable

Thu, 11 Jan
YYZ
ORD
6h 03m
Tue, 16 Jan
ORD
YYZ
5h 18m
C$ 263
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13550 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
LHR
Excellent 8.0

I booked via Kayak using Virgin Atlantic shared out to Delta. Check was confusing as both airlines used different flight numbers. When I went to check in with Virgin Atlantic they told me to go to Delta. When I went to Delta they told me to go back to Virgin Atlantic. I wound up checking in with Virgin Atlantic. Everyone was very polite but check in was confusing. Everything else was wonderful. Cutomer service was great from beginning to end.

Check in.

JFK
ATL
Mediocre 2.0

We landed

No drinks served , could not leave our seats , 2 hr flight turned into 3 hrs

RSW
ATL
Excellent 10.0

cleanliness; attendants were very helpful

ATL
PDX
Excellent 8.6

Great entertainment, comfortable seats.

Middle seat with zero chance to switch.

DTW
MCO
Good 7.3

I paid for an upgraded seat and it was still very cramped

Wed, 14 Feb
YYZ
ORD
1h 47m
Mon, 19 Feb
ORD
YYZ
1h 39m
C$ 305
Trip: 6 days
6.0GoodShow reviews
Overall 6.0 Good
Based on 60 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
YYZ
ORD
Good 6.3

Crew was curteous and capable

The screens on the back of seats that used to play movies now play advertisements and ask you to pay for in-flight entertainment. The off button did not turn the screen off, resulting in a constant eyesore for the entire trip

YYZ
ORD
Excellent 8.5

I don't fully understand why, but I was unable to get my boarding pass for my flight to Chicago from Toronto until I arrived in the Toronto airport. Toronto airport sequesters off international arrivals, so in an ideal world, I would have been able to go through security directly to into the U.S. terminal, bypassing Canada customs. However, the United desk that I needed to get my boarding pass from located just before security was unmanned. The very kind Air Canada attendant called for a representative multiple times, but after 45 minutes of waiting no one ever arrived to print my boarding pass for me. The Air Canada employee then gave up on any United staff showing up and suggested I try going through Canadian customs and checking in at the same departure desk travelers first entering the airport would go through and make sure to let them know how long I was waiting. The United employee I spoke with told me that I was impatient and should have continued waiting because now she didn't know what would happen with my checked bag and that I may well need to wait 2 hours more for that to get sorted out. I was rather surprised by her overly negative response and apparent threat. If I was irate or yelling that might have been warranted, but frankly, I was so tired from the international travel I didn't have the energy to fight with her. Regardless, I wish I had been more impatient, it was far easier to go through customs twice than I expected. I would have preferred to spend more time in the lounge inside the terminal than to stand by the United desk waiting for someone to arrive to print my boarding pass. At any rate, Canadian+US customs have it together; when I went through U.S. customs to get into the terminal they had the photo of my checked bag right there.

YYZ
ORD
Okay 4.6

Ok

Cannot gauge if carry-on would fit into overhead No entertainment

YYZ
ORD
Okay 5.3

Flight was on time and short in duration

Seats rows were narrow with just enough leg room. Very confining and uncomfortable. Our row did not recline as we were in front of the exit row. Luckily, the person in front of me did not recline their seat back.

YYZ
ORD
Okay 4.0

I didn't like nothing

United needs to training your employees

Mon, 21 May
YYZ
ORD
1h 42m
Wed, 23 May
ORD
YYZ
1h 31m
C$ 340
Trip: 3 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 190 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYZ
ORD
Excellent 10.0

Everything was great

YYZ
ORD
Okay 5.2

I arrived at the gate and looked at my ticket to see "GTE" where the seat number usually is. I was informed upon arriving at the desk at the gate that that meant Air Canada has also decided to participate in the ridiculous practice of overbooking their flights and that even though I purchased my ticket roughly 8 weeks prior, there was a chance I might miss my flight to my friend's WEDDING. The lady who was working the desk was as unhelpful and dismissive as you could possibly imagine, refusing to look at me and giving me attitude for merely waiting in the area to see if anyone had missed the flight so I could get on. It was surreal; the only way I could describe her incomprehensible behavior would be to say it was as if her boss were right in front of her and she was trying her damnedest to get fired. It was one of those situations where you could tell this miserable, miserable person was enjoying the power trip she was on and doing everything in her power to make me feel helpless and angry. I made my flight, miraculously, but it was the worst customer service experience I have ever had in my life, airport or not.

YYZ
ORD
Excellent 10.0

كل شي

YYZ
ORD
Mediocre 3.0

Low fare

Flight delayed initially due to weather. When weather cleared flight delayed half hour because they could not find the pilot.

YYZ
ORD
Mediocre 2.0

At the gate, we were told our plane would leave soon. An hour later, they announced the flight was cancelled and we were briskly escorted out of the terminal, told to go through customs and pick up our luggage, which had never even made it on to the plane. They were not re-booking flights at the airport, and the phone lines went to a voice mail message telling us to call back in a few days. I was stranded in Toronto with no phone and no where to stay. It's a week later and I still have not heard anything from from, even though I've called and emailed and sent snail mail.

Sat, 2 Dec
YYZ
ORD
4h 03m
Sun, 10 Dec
ORD
YYZ
1h 31m
C$ 285
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 19 Jan
YYZ
ORD
4h 58m
Wed, 24 Jan
ORD
YYZ
3h 22m
C$ 263
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13550 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ATL
Excellent 9.0

No meal service in first class.

RSW
ATL
Excellent 10.0

cleanliness; attendants were very helpful

DTW
MCO
Good 7.3

I paid for an upgraded seat and it was still very cramped

MSP
BWI
Excellent 10.0

I am 6’3” and have difficulty with leg room on planes. Staff help me out by moving my son and I to Comfort seating row.

TLV
JFK
Excellent 8.0

Landing was frightening.

Mon, 29 Jan
YYZ
ORD
1h 57m
Mon, 5 Feb
ORD
YYZ
7h 16m
C$ 286
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 6 Jan
YYZ
ORD
1h 56m
Tue, 9 Jan
ORD
YYZ
1h 40m
C$ 318
Trip: 4 days
5.3OkayShow reviews
Overall 5.3 Okay
Based on 5 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
JFK
GRU
Good 6.0

It got me there safely without delays.

Food isn't good. the connections can be offered in a much better and time efficient way but they were not. I had to change airports in NYC with a 7-hr layover while they could've flown me to JFK (there was available flights). Same thing with coming back, a long layover in Texas.

LAX
HND
Good 6.3

served snacks without drinks or at least water

BHM
ORD
Excellent 10.0

The flight was a quick 39 minutes from Chicago, the staff was friendly. Good flight.

It's snowing!

ORD
MLI
Good 7.3

All great

Food and entertainment not applicable

YYZ
ORD
Good 7.6

Staff seemed tired with some minor conflicts between them at Toronto gate

Thu, 25 Jan
YYZ
ORD
7h 31m
Sun, 28 Jan
ORD
YYZ
7h 10m
C$ 263
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13550 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
RSW
ATL
Excellent 10.0

cleanliness; attendants were very helpful

JFK
ATL
Mediocre 2.0

We landed

No drinks served , could not leave our seats , 2 hr flight turned into 3 hrs

ATL
HOU
Excellent 10.0

same

SAN
LAX
Good 7.0

No entertainment

JFK
LHR
Excellent 8.0

I booked via Kayak using Virgin Atlantic shared out to Delta. Check was confusing as both airlines used different flight numbers. When I went to check in with Virgin Atlantic they told me to go to Delta. When I went to Delta they told me to go back to Virgin Atlantic. I wound up checking in with Virgin Atlantic. Everyone was very polite but check in was confusing. Everything else was wonderful. Cutomer service was great from beginning to end.

Check in.

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Prices are per person, are for e–tickets and include all taxes & fees in CAD.

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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.