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

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FAQs for Booking Toronto to Chicago Flights

How long does a flight from Toronto to Chicago take?
An average nonstop flight takes 1h 50m, covering a distance of 702 km.
How many flights are there between Toronto and Chicago?
There are 822 (nonstop) flights between Toronto and Chicago per week, averaging 119 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 Porter Airlines (C$ 240), Multiple Airlines (C$ 241) and Delta (C$ 263).
Do I need a passport to fly between Toronto and Chicago?
Yes.
Which airlines fly most frequently between Toronto and Chicago?
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?
For Toronto to Chicago, Friday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago back to Toronto, the best deals are generally found on Thursday, with Tuesday being the most expensive.

Good to Know

Low Season:
February
Best time to beat the crowds
3%
expected price decrease
High Season:
March
Most popular time to fly
4%
expected price increase
Average price:
C$ 420
(avg. price over the last 2 weeks)
Good Deal:
C$ 298
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

When looking for a cheap flight, consider that 25% of our users selected a flight on this route for C$ 298 or less.
The cheapest flight from Toronto to Chicago was found, on average, 79 days before departure.
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 29% 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

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

Airports
Origin
Toronto
C$ 241
only
C$ 241
C$ 240
only
C$ 240
Destination
Chicago
C$ 241
only
C$ 241
C$ 240
only
C$ 240
Fri, 8 Dec
YTZ
MDW
1h 50m
Sun, 10 Dec
MDW
YTZ
1h 37m
C$ 240
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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 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.

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 10.0

Good

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
Fri, 8 Dec
YYZ
ORD
6h 25m
Wed, 31 Jan
ORD
YYZ
6h 03m
C$ 263
Trip: 55 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
LGA
CVG
Excellent 8.3

Plane was far too tight. Very uncomfortable for taller individuals.

YUL
ATL
Good 6.0

Fligth were on time

My flight from Montreal to Atlanta was 2:30 min Left at 6:10 arrive at 8:30 roughly Tried twice to get to my connection earlier and get 9:30 instead of 12:09 fligth to Daytona Delta was not flexible to allow me to book saying i did not have 55 min in between fligth which i had than lear n it will cost $75.00 to change the fligth - What? Very disappointed of Delta - lost 3 hrs at the airport today

ATL
SNA
Excellent 8.0

4 hour flight. Non-eventful except slight turbulence. Good to be home! Thank you!

NA

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

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.

Sat, 9 Dec
YTZ
MDW
1h 50m
Tue, 12 Dec
MDW
YTZ
1h 35m
C$ 240
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

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 8.3

fast

no TSA precheck

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.

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

Thu, 7 Dec
YYZ
ORD
1h 59m
Wed, 13 Dec
ORD
YYZ
1h 31m
C$ 258
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 9 Dec
YYZ
ORD
8h 00m
Tue, 12 Dec
ORD
YYZ
5h 02m
C$ 263
Trip: 4 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
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

JFK
JAX
Good 7.6

Delta never used to be my first choice in airlines, but of my recent experience with them has been excellent. The people from the counter to the plane have been professional and courteous. This is why I will fly with them more frequently.

LGA
CVG
Excellent 8.3

Plane was far too tight. Very uncomfortable for taller individuals.

BUF
ATL
Excellent 10.0

I asked for a change of seat at the gate and was given it. It really made a difference to be at the window.

YUL
ATL
Good 6.0

Fligth were on time

My flight from Montreal to Atlanta was 2:30 min Left at 6:10 arrive at 8:30 roughly Tried twice to get to my connection earlier and get 9:30 instead of 12:09 fligth to Daytona Delta was not flexible to allow me to book saying i did not have 55 min in between fligth which i had than lear n it will cost $75.00 to change the fligth - What? Very disappointed of Delta - lost 3 hrs at the airport today

Thu, 14 Dec
YTZ
MDW
1h 50m
Sun, 31 Dec
MDW
YTZ
1h 37m
C$ 240
Trip: 18 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

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.

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 6.0

Efficient

Late flight

Fri, 8 Dec
YYZ
ORD
1h 59m
Wed, 13 Dec
ORD
YYZ
1h 31m
C$ 258
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sun, 10 Dec
YYZ
ORD
6h 25m
Thu, 14 Dec
ORD
YYZ
5h 02m
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
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

ATL
MCO
Excellent 10.0

Amazing experience thank you Delta

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.

LGA
CVG
Excellent 8.3

Plane was far too tight. Very uncomfortable for taller individuals.

YUL
ATL
Good 6.0

Fligth were on time

My flight from Montreal to Atlanta was 2:30 min Left at 6:10 arrive at 8:30 roughly Tried twice to get to my connection earlier and get 9:30 instead of 12:09 fligth to Daytona Delta was not flexible to allow me to book saying i did not have 55 min in between fligth which i had than lear n it will cost $75.00 to change the fligth - What? Very disappointed of Delta - lost 3 hrs at the airport today

Fri, 15 Dec
YTZ
MDW
1h 50m
Sun, 31 Dec
MDW
YTZ
1h 37m
C$ 240
Trip: 17 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

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 8.3

fast

no TSA precheck

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

Thu, 14 Dec
YYZ
ORD
2h 00m
Tue, 19 Dec
ORD
YYZ
1h 31m
C$ 258
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 11 Jan
YYZ
ORD
6h 03m
Mon, 15 Jan
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
CHA
ATL
Excellent 10.0

On time departure and arrival. The Airbus plane has enough legroom for tall persons.

ATL
MCO
Excellent 10.0

Amazing experience thank you Delta

LGA
CVG
Excellent 8.3

Plane was far too tight. Very uncomfortable for taller individuals.

LAX
GUA
Mediocre 2.0

Nothing worst flight I've ever had.

Everything Delta was so poor quality!!! The flight attendants were not helpful.

ATL
SNA
Excellent 8.0

4 hour flight. Non-eventful except slight turbulence. Good to be home! Thank you!

NA

Thu, 21 Dec
YTZ
MDW
1h 50m
Sun, 24 Dec
MDW
YTZ
1h 37m
C$ 240
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Excellent 10.0

Good

Tue, 12 Dec
YYZ
ORD
1h 58m
Mon, 18 Dec
ORD
YYZ
5h 24m
C$ 263
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, 16 Jan
YYZ
ORD
7h 31m
Sun, 28 Jan
ORD
YYZ
7h 10m
C$ 263
Trip: 13 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
YUL
ATL
Good 6.0

Fligth were on time

My flight from Montreal to Atlanta was 2:30 min Left at 6:10 arrive at 8:30 roughly Tried twice to get to my connection earlier and get 9:30 instead of 12:09 fligth to Daytona Delta was not flexible to allow me to book saying i did not have 55 min in between fligth which i had than lear n it will cost $75.00 to change the fligth - What? Very disappointed of Delta - lost 3 hrs at the airport today

MOB
ATL
Good 6.0

Felt like I was sitting in my neighbors lap!

LAX
GUA
Mediocre 2.0

Nothing worst flight I've ever had.

Everything Delta was so poor quality!!! The flight attendants were not helpful.

ATL
MCO
Excellent 10.0

Amazing experience thank you Delta

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

Sun, 7 Jan
YTZ
MDW
1h 50m
Wed, 10 Jan
MDW
YTZ
1h 37m
C$ 251
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Mediocre 2.0

Nothing

Everything

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.

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

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.

Wed, 13 Dec
YYZ
ORD
1h 58m
Mon, 18 Dec
ORD
YYZ
5h 24m
C$ 263
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 20 Jan
YYZ
ORD
7h 50m
Mon, 22 Jan
ORD
YYZ
7h 16m
C$ 263
Trip: 3 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
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.

ATL
SNA
Excellent 8.0

4 hour flight. Non-eventful except slight turbulence. Good to be home! Thank you!

NA

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

BUF
ATL
Excellent 10.0

I asked for a change of seat at the gate and was given it. It really made a difference to be at the window.

LAX
GUA
Mediocre 2.0

Nothing worst flight I've ever had.

Everything Delta was so poor quality!!! The flight attendants were not helpful.

Wed, 13 Dec
YTZ
MDW
1h 50m
Wed, 20 Dec
MDW
YTZ
1h 37m
C$ 256
Trip: 8 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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 6.6

Onboard crew was very nice

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

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 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.

Thu, 14 Dec
YYZ
ORD
1h 58m
Mon, 18 Dec
ORD
YYZ
4h 00m
C$ 263
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Show more results
*
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.