Find Cheap Flights from Toronto to Chicago (YTO - CHI)

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Thu 1/18
Thu 1/25
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Good to Know

Low Season:
February
Best time to beat the crowds
2%
expected price decrease
High Season:
March
Most popular time to fly
4%
expected price increase
Average Price:
$634
(avg. price over the last 2 weeks)
Good Deal:
$634
or less (round trip)

When to Book Flights from Toronto to Chicago

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

Top tips for Finding a Cheap Flight

The cheapest flight from Toronto to Chicago was found 79 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be February, March and April. The cheapest month to fly is February.
Morning departure is around 6% 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 Flights

How long does a flight from Toronto to Chicago take?
An average nonstop flight takes 1h 42m, covering a distance of 436 miles.
How many flights are there between Toronto and Chicago?
There are 548 (nonstop) flights between Toronto and Chicago per week, averaging 80 per day.
Which airlines provide the cheapest flights from Toronto to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($211), Porter Airlines ($218) and Multiple Airlines ($219).
Do I need a passport to fly between Toronto and Chicago?
Yes.
Which airlines fly most frequently between Toronto and Chicago?
United (12 times daily), Air Canada (11 times daily), Porter Airlines (8 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Toronto to Chicago?
For Toronto to Chicago, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Toronto, the best deals are generally found on Friday, with Tuesday being the most expensive.

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

Airports
Origin
Toronto
$211
only
$211
$218
only
$218
Destination
Chicago
$211
only
$211
$218
only
$218
Mon, Feb 5
YYZ
ORD
5h 02m
Wed, Feb 7
ORD
YYZ
6h 46m
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
SYR
JFK
Good 7.0

Nothing Special

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

SAN
LAX
Excellent 10.0

on time

Sat, Feb 10
YTZ
MDW
1h 50m
Wed, Feb 21
MDW
YTZ
1h 37m
Trip: 12 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

Thu, Mar 1
YYZ
ORD
1h 57m
Tue, Mar 20
ORD
YYZ
1h 31m
Trip: 19 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 6
YYZ
ORD
1h 47m
Thu, Mar 15
ORD
YYZ
1h 31m
Trip: 9 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 199 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYZ
ORD
Mediocre 2.0

Seats for connecting flight were given away before connecting flight boarded and rescheduled flights didn’t provide purchased level of service

YYZ
ORD
Excellent 8.0

The flight was on time and there was adequate foot room

No free snacks- biscuits or pretzels?

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
Good 7.0

The movies on board

The fact the plane was late

YYZ
ORD
Good 7.0

Had extra space because plane was not full

Flight was delayed. Changed gate three times

Wed, Mar 28
YYZ
ORD
2h 02m
Thu, Mar 29
ORD
YYZ
1h 42m
Trip: 2 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 7 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

TPA
PHX
Excellent 9.3

We had a newer plane. I LOVED that the seatbelts had a little more room, and also that each seat had it down screen. I really enjoyed the new pre-flight video; it was entertaining and I appreciated that it allowed the crew to get ready, rather than demonstrate a seatbelt for us.

I am not sure how boarding groups work, but I will never understand why we don't board from the back of the plane to the front. People waiting and trying to load luggage or climb over others makes the pre-flight more stressful than it needs to be. (This is obviously not specific to you airline.)

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

DFW
SFO
Good 6.0

The seats actually had individual screens, which was a very nice surprise. There’s a decent movie collection. alao the flight attendants were very nice and friendly.

The tv show selection is quite poor. Also, like the previous flight, my husband and I weren’t seated together (not even in the same row) and when I tried to change it online, the entire flight showed as booked. However once on board there were clearly a number of empty seats.

DFW
MSY
Excellent 10.0

Travel time

No snacks on flight. The charging stations come in between legs space and very uncomfortable they got to be re adjusted. Make sure these are taken care in upcoming flights.

Thu, May 24
YYZ
ORD
1h 42m
Tue, May 29
ORD
YYZ
1h 32m
Trip: 6 days
6.0GoodShow reviews
Overall 6.0 Good
Based on 61 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
YYZ
ORD
Mediocre 2.0

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

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 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

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.

Tue, Feb 6
YYZ
ORD
5h 55m
Wed, Feb 14
ORD
YYZ
5h 10m
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
YUL
DTW
Mediocre 2.0

Not applied

Not applied

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

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

Thu, Feb 22
YTZ
MDW
1h 50m
Sun, Feb 25
MDW
YTZ
1h 37m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

Delay

YTZ
MDW
Good 6.6

Onboard crew was very nice

Crew didn't answer any of my questions, were snappy, and rude.

Thu, Apr 12
YYZ
ORD
1h 51m
Sun, Apr 15
ORD
YYZ
1h 33m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 7
YYZ
ORD
1h 47m
Thu, Mar 15
ORD
YYZ
1h 31m
Trip: 8 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 199 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYZ
ORD
Mediocre 2.0

Seats for connecting flight were given away before connecting flight boarded and rescheduled flights didn’t provide purchased level of service

YYZ
ORD
Good 7.0

Had extra space because plane was not full

Flight was delayed. Changed gate three times

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 10.0

كل شي

YYZ
ORD
Excellent 8.0

The flight was on time and there was adequate foot room

No free snacks- biscuits or pretzels?

Fri, Mar 30
YYZ
ORD
2h 02m
Wed, Apr 4
ORD
YYZ
10h 43m
Trip: 6 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 7 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CDG
DFW
Good 6.3

The snacks and meals were decent, as far as plane food goes (although the “vegetables” with the chicken were pretty awful). Also the entertainment selection had a wide assortment of movies, but disappointing tv show selection.

The boarding process was a mess. Just a huddle of people, with no clear direction and no one enforcing lines or boarding groups. Also my husband and I weren’t seated together and when I tried to change it online, the entire flight showed as booked. However once on board there were clearly a number of empty seats.

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

DFW
SFO
Good 6.0

The seats actually had individual screens, which was a very nice surprise. There’s a decent movie collection. alao the flight attendants were very nice and friendly.

The tv show selection is quite poor. Also, like the previous flight, my husband and I weren’t seated together (not even in the same row) and when I tried to change it online, the entire flight showed as booked. However once on board there were clearly a number of empty seats.

LAX
AKL
Excellent 8.3

New plane, great crew on board.

seats were hard especially for a 13 1/2 hour flight.

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!!!!!

Wed, Feb 7
YYZ
ORD
5h 55m
Wed, Feb 14
ORD
YYZ
5h 10m
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
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.

SAN
LAX
Excellent 10.0

on time

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

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.

Thu, Mar 1
YTZ
MDW
1h 50m
Tue, Mar 20
MDW
YTZ
1h 37m
Trip: 19 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 6.6

Onboard crew was very nice

Crew didn't answer any of my questions, were snappy, and rude.

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Mon, Feb 12
YYZ
ORD
1h 57m
Fri, Feb 16
ORD
YYZ
1h 31m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 16
YYZ
ORD
1h 47m
Sun, Mar 25
ORD
YYZ
1h 33m
Trip: 10 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 199 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
Excellent 10.0

كل شي

YYZ
ORD
Excellent 8.0

The flight was on time and there was adequate foot room

No free snacks- biscuits or pretzels?

YYZ
ORD
Excellent 10.0

Everything was great

YYZ
ORD
Mediocre 2.0

Seats for connecting flight were given away before connecting flight boarded and rescheduled flights didn’t provide purchased level of service

Thu, Feb 8
YYZ
ORD
5h 55m
Wed, Feb 14
ORD
YYZ
6h 56m
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
AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

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.

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.

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, Mar 8
YTZ
MDW
1h 50m
Tue, Mar 13
MDW
YTZ
1h 37m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Good 7.3

Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight.

Louder than a usual commercial flight, probably due to being a turboprop aircraft.

Fri, Feb 23
YYZ
ORD
1h 59m
Mon, Feb 26
ORD
YYZ
1h 31m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 26
YYZ
ORD
1h 57m
Sun, Apr 1
ORD
YYZ
1h 40m
Trip: 7 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 199 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYZ
ORD
Good 7.0

Had extra space because plane was not full

Flight was delayed. Changed gate three times

YYZ
ORD
Mediocre 2.0

Seats for connecting flight were given away before connecting flight boarded and rescheduled flights didn’t provide purchased level of service

YYZ
ORD
Excellent 10.0

Everything was great

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

Meh

Meh

Fri, Feb 9
YYZ
ORD
6h 27m
Wed, Feb 14
ORD
YYZ
5h 10m
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
AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

DEN
SLC
Excellent 10.0

Delta is great

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

SYR
JFK
Good 7.0

Nothing Special

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

Show more results

Toronto to Chicago Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Chicago
Flights Depart from Toronto
Flight Price $211
Distance 436 miles
Airlines Delta, Porter Airlines, Air Canada, American Airlines, United
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

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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.

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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.