Find Cheap Flights from Canada to Chicago

Search hundreds of travel sites at once for deals on flights to Chicago

Wed 2/21
Wed 2/28
Any month
Compare vs. KAYAK |

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

Airports
Origin
Hamilton
$261
only
$261
Montreal
$246
only
$246
Toronto
$219
only
$219
$216
only
$216
Destination
Chicago
$219
only
$219
$216
only
$216
Thu, Apr 5
YTZ
MDW
1h 50m
Thu, Apr 12
MDW
YTZ
1h 40m
Trip: 8 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
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

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Good 6.0

Efficient

Late flight

Thu, Mar 22
YYZ
ORD
1h 59m
Mon, Mar 26
ORD
YYZ
1h 31m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jun 9
YYZ
ORD
1h 54m
Sat, Jun 16
ORD
YYZ
1h 58m
Trip: 8 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 8 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
SAT
DFW
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Nothing to complain about. I was satisfied with this flight.

DTW
MIA
Excellent 8.0

Easy check in.

Service staff was friendly enough; maybe I’m used to southwest. As someone who is anxious to fly smiling faces are always appreciate.

PHL
SFO
Good 7.6

Tight connection! The airlines need to Realize that a 2 hour layover is NOT enough when you have to go through immigration, customs, and security before making your next flight!

ORD
CLE
Excellent 10.0

It was a very good fight

I didn't like the fact that the gate kept on changed 3-4 times and that it was delayed for an hour

YYZ
ORD
Good 7.6

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

Tue, Mar 27
YYZ
MDW
4h 53m
Wed, Apr 4
MDW
YYZ
4h 55m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

LAX
JFK
Excellent 10.0

I was able to pass the time with ease. A+++ in flight experiences. Great airline staff and awesome food.

No complaints whatsoever.

JFK
LAX
Excellent 10.0

The in flight entertainment was superb.

I have no complaints.

ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

ATL
CUN
Good 6.3

The crew was outstanding, polite, and professional.

Seats were comfortable, but much too crowded. The seating would have been very good for children but for adults it was much too crowded. My knees were up against the seat in front and my back is sore from having to spend most of the trip twisted to try to fit into the small space. Also, my seat was is row 16 and was called a “premium” seat and I was charged an extra $24 for it. I did not find it any different than all the seats around me. What was the extra charge for?

Mon, Mar 26
YTZ
ORD
5h 15m
Sat, Mar 31
ORD
YTZ
4h 40m
Trip: 6 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 21506 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYJ
YYZ
Okay 4.0

The flight wasn’t full, so I sat in my own row,?which offered spare leg room (I’m 6’2”). Time to fix the leg room issue on Rouge flights — it’s 2018.

Crew seemed uninterested in general. On phones in back while people struggling to find luggage space. Coffee cups and plastic utensils, etc, stored in overhead bins so people at the back had to search for carry-on space elsewhere, again, without assistance from on board crew. Offered service only once and many were sleeping so didn’t get anything. The overall check-in process could be easier, as the app doesn’t always work as it should.

YYZ
FLL
Excellent 9.3

The crew at the airport and on the plane were excellent. We were on a family holiday with young ones and the crew really took care of our needs. They were extremely courteous and attentive.

The inflight entertainment options could be more current. We found the options limited... it was a good thing that the flight was short.

YYZ
BOS
Okay 4.0

That we eventually got a flight home.

Being stuck in Boston and Ottawa for 2 extra days and adding around $1200 on to our trip in hotels alone (I was travelling with 4 kids on a school trip and my wife). Additionally, we didn’t find out the flights were cancelled until we arrived at the airport. Apparently, they had been cancelled 2 hours before but there was no notification. Air Canada offered no help whatsoever and the guy at the “service” desk in Boston literally said there was nothing he could do to help. Not even find a new flight. Spent 90 minutes on the phone trying to re-book, plus re-booking hotel along the way.

YVR
TPE
Okay 5.6

Entertainment

Steward. & meals

YYC
YYZ
Good 7.0

Able to Get later flight since original flight cancelled.

flight delayed 2 hrs because of weather. Staff did not want to reschedule my next connector, just the Toronto flight

Tue, Apr 3
YUL
ORD
2h 50m
Sun, Apr 8
ORD
YUL
2h 09m
Trip: 6 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 25 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
YUL
ORD
Okay 4.6

I still got to Grand Rapids on time but connecting flight forced me to run through ohare

Plan small. Late departing from montreal

SFO
PHL
Mediocre 2.3

Crew was nice

I hated my seat. Last row. Seat didn’t recline. Right next to the bathroom. That should not even be a row for passengers!

YUL
ORD
Excellent 10.0

Boarding was quick, staff was friendly and helpful.

No in flight entertainment...

YUL
ORD
Mediocre 2.0

I was put on an Air Canada flight and sat on the tarmac for almost THREE hours in MTL. Finally took off and am stuck in Toronto overnight. Air Canada was very unhelpful. I have to sleep in the airport. No food vouchers. Sucks.

YUL
ORD
Good 6.3

The seats in this small plane were comfortable with decent spacing, decent legroom.

One flight attendant, too much work for one.. $8 dollars to use tv, $6 for wifi.

Sat, Apr 28
YTZ
MDW
1h 45m
Fri, May 4
MDW
YTZ
1h 40m
Trip: 7 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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 10.0

Good

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

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 8.0

Delay

Thu, Apr 5
YYZ
ORD
1h 57m
Thu, Apr 12
ORD
YYZ
1h 33m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 20
YTZ
MDW
1h 50m
Thu, Mar 22
MDW
YTZ
1h 37m
Trip: 3 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
Mediocre 2.0

Nothing

Everything

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

Delay

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Good 6.0

Efficient

Late flight

Tue, Apr 10
YYZ
ORD
1h 49m
Tue, Apr 17
ORD
YYZ
1h 33m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 3
YYZ
MDW
3h 31m
Tue, Apr 10
MDW
YYZ
4h 43m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
CUN
Good 6.3

The crew was outstanding, polite, and professional.

Seats were comfortable, but much too crowded. The seating would have been very good for children but for adults it was much too crowded. My knees were up against the seat in front and my back is sore from having to spend most of the trip twisted to try to fit into the small space. Also, my seat was is row 16 and was called a “premium” seat and I was charged an extra $24 for it. I did not find it any different than all the seats around me. What was the extra charge for?

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

JFK
LAX
Excellent 10.0

The in flight entertainment was superb.

I have no complaints.

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

MEX
LAX
Excellent 10.0

The Delta flight was such a pleasant contrast to the funky Interjet flight that I took from L.A. to Mexico that my Economy Class felt like First Class.

Thu, May 31
YYZ
ORD
1h 48m
Thu, Jun 7
ORD
YYZ
1h 41m
Trip: 8 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 62 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
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 4.0

I didn't like nothing

United needs to training your employees

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
Mediocre 2.0

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

Tue, Jul 31
YYZ
ORD
1h 54m
Sat, Aug 4
ORD
YYZ
1h 44m
Trip: 5 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 8 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
ORD
CLE
Excellent 10.0

It was a very good fight

I didn't like the fact that the gate kept on changed 3-4 times and that it was delayed for an hour

TUS
CLT
Excellent 10.0

No free wifi

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!!!!!

SAT
MIA
Excellent 10.0

All

Nothing

PHL
SFO
Good 7.6

Tight connection! The airlines need to Realize that a 2 hour layover is NOT enough when you have to go through immigration, customs, and security before making your next flight!

Fri, Mar 23
YHM
ORD
4h 35m
Sat, Mar 24
ORD
YHM
6h 47m
Trip: 2 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 21506 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
FLL
Excellent 9.3

The crew at the airport and on the plane were excellent. We were on a family holiday with young ones and the crew really took care of our needs. They were extremely courteous and attentive.

The inflight entertainment options could be more current. We found the options limited... it was a good thing that the flight was short.

YVR
TPE
Okay 5.6

Entertainment

Steward. & meals

ICN
YYZ
Excellent 9.6

This was my first time flying Air Canada. Our flight was delayed by 4 hours because they had to deice the plane. Yes it was frustrating but I would much rather have a flight of upset passengers then risking our lives. The captains and the crew went out of their way to make sure that we were the most comfortable. They gave us food and drinks as we waited and were extremely patient. Upon arrival many passengers had missed their connecting flights, including myself. They put us on the next flight out and gave all passengers a hotel and meals for the night. I would definitely recommend Air Canada. The plane itself is also pretty spacious so don’t be afraid to fly economy.

Nothing really. They were great. I mean, definitely wished my flight wasn’t delayed. Although It wasn’t their fault that they needed to deice the plane, that’s something that should’ve been accounted for way before our flight was supposed to take off.

LHR
YYZ
Excellent 8.3

The food was ok. Movie selection was decent and the screens are a lot better than on jet airways.

Boarding was a little delayed. Service was a little slow, but the crew was courteous and did their best.

YYZ
RSW
Excellent 8.0

Bags were available when we got to carousel

It took longer than average for them to open doors once at gate. That’s probably why bags were available.

Thu, Jun 14
YTZ
MDW
1h 45m
Thu, Jun 21
MDW
YTZ
1h 40m
Trip: 8 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 10.0

Good

YTZ
MDW
Excellent 8.0

Delay

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
Excellent 8.3

fast

no TSA precheck

Tue, Apr 10
YYZ
MDW
6h 09m
Tue, Apr 17
MDW
YYZ
7h 33m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

LAX
JFK
Excellent 10.0

I was able to pass the time with ease. A+++ in flight experiences. Great airline staff and awesome food.

No complaints whatsoever.

DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

Mon, Aug 20
YYZ
ORD
1h 54m
Sat, Aug 25
ORD
YYZ
1h 36m
Trip: 6 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 8 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
SAT
MIA
Excellent 10.0

All

Nothing

DTW
MIA
Excellent 8.0

Easy check in.

Service staff was friendly enough; maybe I’m used to southwest. As someone who is anxious to fly smiling faces are always appreciate.

BUF
PHL
Mediocre 2.0

None of the experience was pleasant

First flight was delayed causing us to miss the 2nd flight and we ended sleeping on a chair at the airport waiting for a morning flight. AMERICAN AIRLINES didn't even have the decency to put us in a hotel for the night due to their delay. Then they added a 2nd lay over which was delayed for hours also. Traveling was to visit my mother who had cancer and I was sick so this made the trip even more distasteful.

DFW
CMH
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Stuffy on the plane. This might not be the airline’s problem but it was hot and the air vent didn’t cool me down.

TUS
CLT
Excellent 10.0

No free wifi

Fri, Jun 22
YTZ
MDW
1h 45m
Wed, Jun 27
MDW
YTZ
1h 40m
Trip: 6 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 6.0

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.

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Excellent 8.0

Delay

Tue, Feb 27
YYZ
ORD
1h 47m
Tue, Mar 13
ORD
YYZ
1h 31m
Trip: 14 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 203 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
ORD
Excellent 8.0

Meh

Meh

YYZ
ORD
Good 6.0

Flight was rescheduled for 4 times ... Every time standing in a line for the new boarding pass

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

كل شي

YYZ
ORD
Good 7.0

Had extra space because plane was not full

Flight was delayed. Changed gate three times

Sun, Mar 25
YUL
ORD
2h 50m
Sat, Mar 31
ORD
YUL
2h 05m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews

Canada to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Canada
Flight Price $216
Airlines Porter Airlines, American Airlines, Delta, Air Canada, 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:

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.