Find Cheap Flights from Toronto to Chicago O'Hare International (YTO - ORD)

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Good to Know

Low Season:
November
Best time to beat the crowds
2%
expected price decrease
High Season:
April
Most popular time to fly
11%
expected price increase
Average price:
C$ 446
(avg. price over the last 2 weeks)
Good Deal:
C$ 304
or less (round trip)

When to Book Flights from Toronto to Chicago O'Hare International

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$ 303 or less.
The cheapest flight from Toronto to Chicago O'Hare International was found, on average, 84 days before departure.
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be March, April and May. The cheapest month to fly is November.
Morning departure is around 21% 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 to Chicago O'Hare International Flights

How long does a flight from Toronto to Chicago O'Hare International take?
An average nonstop flight takes 1h 42m, covering a distance of 719 km.
How many flights are there between Toronto and Chicago O'Hare International?
There are 754 (nonstop) flights between Toronto and Chicago O'Hare International per week, averaging 109 per day.
Which airlines provide the cheapest flights from Toronto to Chicago O'Hare International?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines (C$ 241), Delta (C$ 263) and United (C$ 281).
Do I need a passport to fly between Toronto and Chicago O'Hare International?
Yes.
Which airlines fly most frequently between Toronto and Chicago O'Hare International?
Air Canada (24 times daily), United (22 times daily), Aer Lingus (11 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from Toronto to Chicago O'Hare International?
For Toronto to Chicago O'Hare International, Friday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago O'Hare International back to Toronto, the best deals are generally found on Thursday, with Tuesday being the most expensive.

Book cheap flights from Toronto to Chicago O'Hare International (round-trip)

Airports
Origin
Toronto
C$ 241
only
C$ 241
C$ 318
only
C$ 318
Destination
Chicago
C$ 241
only
C$ 241
Fri, 8 Dec
YYZ
ORD
1h 59m
Mon, 11 Dec
ORD
YYZ
1h 31m
C$ 241
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 1 Feb
YYZ
ORD
7h 31m
Mon, 5 Feb
ORD
YYZ
7h 16m
C$ 263
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13528 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
BNA
Excellent 10.0

Compared to previous flight - this was so much better with upgrade to first class and extra space.

DTW
EWR
Excellent 8.0

Boarding was quick. Staff and crew were friendly. Everything went well despite the 30 min delay we had on the runway. They gave us snacks and we ended up still arriving on time.

JFK
LAX
Excellent 9.3

Check in was easy through their app. Also very quick lines to drop off bags. Crew was very nice and respectful

Seat are a little bit too close together. But overall very comfortable

MOB
ATL
Good 6.0

Felt like I was sitting in my neighbors lap!

ATL
MCO
Excellent 10.0

Amazing experience thank you Delta

Fri, 9 Feb
YYZ
ORD
1h 59m
Sun, 11 Feb
ORD
YYZ
1h 35m
C$ 281
Trip: 3 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 59 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
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
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

Nothing

Everything

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 4.0

united over book. i got boarding pass but no seat number. United charge me $400. I want me money back.

Fri, 25 May
YYZ
ORD
1h 54m
Sun, 27 May
ORD
YYZ
1h 36m
C$ 287
Trip: 3 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
Okay 4.6

Friendly crew

Zero Entertainment. Flight delayed around 30 minutes, which gave me a heartburn as we had to catch the next flight. No priority plus lounge near this gate in Toronto

PWM
PHL
Okay 4.6

We arrived on time.

These planes feel like they are made of Legos. They are absurdly tiny and uncomfortable (and I am a small woman). Hot and stinky when boarding and no room for you or your carry on luggage. The days of glamorous air travel seem very far away.

YYZ
ORD
Good 7.6

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

LAX
MIA
Good 7.6

Movies, clean, efficient

Paying of my small Checked bag

BDL
CLT
Okay 4.0

No baggage controls from seat 18 to 28 no bags would fit. As we exited all the front rows we're waiting to get there bags stored in back of planes overhead bins. That's just not right, especially when they charge us extra to take a bag for overhead bins storage.

Sun, 7 Jan
YYZ
ORD
1h 47m
Wed, 10 Jan
ORD
YYZ
1h 31m
C$ 297
Trip: 4 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
Excellent 10.0

كل شي

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
Excellent 8.0

service on the plane was good and the crew was very nice to be patient while we boarded the plane with 3 little kids

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.

Fri, 8 Dec
YYZ
ORD
1h 59m
Sun, 10 Dec
ORD
YYZ
1h 31m
C$ 267
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Mon, 2 Apr
YYZ
ORD
1h 52m
Fri, 6 Apr
ORD
YYZ
1h 33m
C$ 283
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 22 Feb
YTZ
ORD
4h 35m
Sun, 25 Feb
ORD
YTZ
4h 40m
C$ 318
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19779 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
TPE
YVR
Good 6.0

Price.

smaller aircraft with very limited overhead bag storage. Constantly have to announce volunteers for bag check in. Happen both ways. Atl to Toronto and Toronto to Atl.

YVR
YYC
Excellent 10.0

Spacious aircraft, great flight attendants very clean bathrooms, lots of snacks and foods

FLL
YUL
Good 7.3

I had to change my return ticket early because of an emergency and Air Canada charged me $481.00 whenI only paid $371.00 fora round trip. How is that possible?

ORD
YYZ
Excellent 8.0

It was overall a good experience, cannot complain about the service as it was great.

The weather caused a bumpy return flight but that is not the airlines fault.

NRT
YVR
Good 7.6

Compared to the flight going the other way, this one was much more comfortable. I didn't have someone's seat back in my face the whole time, and was able to enjoy games on my own device. I like that both USB and normal power options were available, so I was able to play games and charge my phone so I could use it after landing. The food was passable as well, which was surprising.

It's unavoidable when flying between multi-lingual locations, but having movies and stuff pause three times for each announcement gets annoying. The rolls served with the meals were very dry. These are small nits, and the flight was generally enjoyable.

Wed, 21 Mar
YYZ
ORD
1h 42m
Sat, 24 Mar
ORD
YYZ
1h 31m
C$ 287
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 16 Mar
YTZ
ORD
5h 10m
Mon, 19 Mar
ORD
YTZ
5h 40m
C$ 319
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19779 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
PVG
YUL
Excellent 9.6

AC 018 takes the shortest route from Shanghai to Montreal. The check in and boarding were like a breeze. Cabin was clean, staff were amiable and hard working. The variety of drinks were plenty, the food matched the standard of cost efficiency flight ticket so how could you complain it? On board TV/Movie has new coming features such as HBO's Game of The Thorne, season 7. It was a comfortable and pleasant journey with the team of AC 018. Merci beaucoup!

ORD
YYZ
Excellent 8.0

It was overall a good experience, cannot complain about the service as it was great.

The weather caused a bumpy return flight but that is not the airlines fault.

LAX
YVR
Excellent 8.4

One of the crewmembers (regrettably, I did not catch his name) was incredibly kind when I moved seats to accommodate a couple that wanted to sit together. He really made this flight great.

Seats were comfortable but the row I moved to did not allow me to recline.

TPE
YVR
Good 6.0

Price.

smaller aircraft with very limited overhead bag storage. Constantly have to announce volunteers for bag check in. Happen both ways. Atl to Toronto and Toronto to Atl.

BWI
YYZ
Excellent 8.0

everything

no entertainment

Fri, 9 Mar
YYZ
ORD
1h 47m
Sun, 11 Mar
ORD
YYZ
1h 31m
C$ 324
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
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
Good 7.0

Had extra space because plane was not full

Flight was delayed. Changed gate three times

YYZ
ORD
Excellent 10.0

كل شي

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 4.3

We landed on time.

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

Thu, 30 Nov
YYZ
ORD
1h 55m
Sun, 3 Dec
ORD
YYZ
5h 05m
C$ 399
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
MBJ
PHL
Excellent 8.6

AA flight was relaxed and smooth, crew was respectful and warm can’t think

Can’t think of anything I didn’t like

MCI
DFW
Mediocre 2.0

I cancelled this flight months ago, yet it was still in your records

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!!!!!

PWM
PHL
Okay 4.6

We arrived on time.

These planes feel like they are made of Legos. They are absurdly tiny and uncomfortable (and I am a small woman). Hot and stinky when boarding and no room for you or your carry on luggage. The days of glamorous air travel seem very far away.

BDL
CLT
Okay 4.0

No baggage controls from seat 18 to 28 no bags would fit. As we exited all the front rows we're waiting to get there bags stored in back of planes overhead bins. That's just not right, especially when they charge us extra to take a bag for overhead bins storage.

Sun, 13 May
YYZ
ORD
1h 54m
Sat, 19 May
ORD
YYZ
1h 31m
C$ 313
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 2 Dec
YYZ
ORD
1h 59m
Mon, 25 Dec
ORD
YYZ
1h 31m
C$ 324
Trip: 24 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 2 Dec
YTZ
ORD
5h 20m
Mon, 4 Dec
ORD
YTZ
4h 40m
C$ 384
Trip: 3 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19779 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
FLL
YUL
Good 7.3

I had to change my return ticket early because of an emergency and Air Canada charged me $481.00 whenI only paid $371.00 fora round trip. How is that possible?

YYZ
YVR
Good 6.3

Food not included with insane flight costs

YUL
LGA
Excellent 10.0

Where do i start? It’s a short flight to be sure but air canada planes never feel like many Other airlines’ mini planes or puddle jumpers. they seem new, spacious, seat back Entertainemnt, just great. Also, there is no scrimping on Service. How many Delta or united or American flights have i taken on this route only to be told “coffee or water” and sometimes no coffee “the flight is too short”. Nonsense! Granted I was in business, but I had a full hot breakfast served and a full array of beverages offered. It AC can do it, everyone can. The flight attendant was lovely.

The flight was too short :)

YVR
YUL
Okay 5.6

I love the variety of entertainment, it never fails.

I didnt like how snacks werent included for my 6 hour flght. Also the amount of waste made with all those plastic cups is astonishingly ridiculous. Switch to a more green solution!!!

LAX
YVR
Excellent 8.4

One of the crewmembers (regrettably, I did not catch his name) was incredibly kind when I moved seats to accommodate a couple that wanted to sit together. He really made this flight great.

Seats were comfortable but the row I moved to did not allow me to recline.

Tue, 28 Nov
YYZ
ORD
5h 40m
Fri, 1 Dec
ORD
YYZ
5h 45m
C$ 390
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 23 Nov
YTZ
ORD
6h 10m
Sun, 26 Nov
ORD
YTZ
6h 35m
C$ 515
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19779 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYZ
YVR
Good 6.3

Food not included with insane flight costs

NRT
YVR
Good 7.6

Compared to the flight going the other way, this one was much more comfortable. I didn't have someone's seat back in my face the whole time, and was able to enjoy games on my own device. I like that both USB and normal power options were available, so I was able to play games and charge my phone so I could use it after landing. The food was passable as well, which was surprising.

It's unavoidable when flying between multi-lingual locations, but having movies and stuff pause three times for each announcement gets annoying. The rolls served with the meals were very dry. These are small nits, and the flight was generally enjoyable.

PVG
YUL
Excellent 9.6

AC 018 takes the shortest route from Shanghai to Montreal. The check in and boarding were like a breeze. Cabin was clean, staff were amiable and hard working. The variety of drinks were plenty, the food matched the standard of cost efficiency flight ticket so how could you complain it? On board TV/Movie has new coming features such as HBO's Game of The Thorne, season 7. It was a comfortable and pleasant journey with the team of AC 018. Merci beaucoup!

ORD
YYZ
Excellent 8.0

It was overall a good experience, cannot complain about the service as it was great.

The weather caused a bumpy return flight but that is not the airlines fault.

YUL
LGA
Excellent 10.0

Where do i start? It’s a short flight to be sure but air canada planes never feel like many Other airlines’ mini planes or puddle jumpers. they seem new, spacious, seat back Entertainemnt, just great. Also, there is no scrimping on Service. How many Delta or united or American flights have i taken on this route only to be told “coffee or water” and sometimes no coffee “the flight is too short”. Nonsense! Granted I was in business, but I had a full hot breakfast served and a full array of beverages offered. It AC can do it, everyone can. The flight attendant was lovely.

The flight was too short :)

Mon, 4 Dec
YTZ
ORD
8h 23m
Thu, 7 Dec
ORD
YTZ
5h 40m
C$ 434
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 18 Nov
YTZ
ORD
4h 45m
Tue, 21 Nov
ORD
YTZ
4h 35m
C$ 532
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19779 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
BWI
YYZ
Excellent 8.0

everything

no entertainment

YVR
YUL
Okay 5.6

I love the variety of entertainment, it never fails.

I didnt like how snacks werent included for my 6 hour flght. Also the amount of waste made with all those plastic cups is astonishingly ridiculous. Switch to a more green solution!!!

ORD
YYZ
Excellent 8.0

It was overall a good experience, cannot complain about the service as it was great.

The weather caused a bumpy return flight but that is not the airlines fault.

YUL
LGA
Excellent 10.0

Where do i start? It’s a short flight to be sure but air canada planes never feel like many Other airlines’ mini planes or puddle jumpers. they seem new, spacious, seat back Entertainemnt, just great. Also, there is no scrimping on Service. How many Delta or united or American flights have i taken on this route only to be told “coffee or water” and sometimes no coffee “the flight is too short”. Nonsense! Granted I was in business, but I had a full hot breakfast served and a full array of beverages offered. It AC can do it, everyone can. The flight attendant was lovely.

The flight was too short :)

YYZ
YVR
Good 6.3

Food not included with insane flight costs

Tue, 5 Dec
YTZ
ORD
8h 23m
Fri, 8 Dec
ORD
YTZ
6h 17m
C$ 440
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
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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.