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Canada to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Canada
Flight Price C$ 241
Airlines Porter Airlines, Major Airline, United Airlines, Air Canada, Delta, WestJet

Top Tips for Finding Cheap Flights to Chicago

Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Toronto C$ 266, from Montreal C$ 326, from Vancouver Intl C$ 369
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be May, June and July. The cheapest month to fly to Chicago is February.
Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

FAQs - Booking Chicago flights

How long is the flight to Chicago?

Flights from Montreal 2h 22m
Flights from Vancouver 4h 20m
Flights from Toronto 1h 44m
Flights from Calgary 3h 36m

What is the cheapest flight to Chicago?

The cheapest airline ticket to Chicago from Canada in the last 72 hours was C$ 241 round-trip on the route Toronto to Chicago. The most popular route is Toronto to Chicago and the cheapest ticket found on this route in the last 72 hours was C$ 544 round-trip.

Which airlines fly to Chicago?

In general from Canada, Air Canada, United Airlines and Air New Zealand fly the most to Chicago. The most popular route is from Toronto, and Air Canada, American Airlines & United Airlines fly this route the most.

Which Chicago airport is closest to central Chicago?

Chicago is served by 3 major airports. Midway (14 kilometres) is the closest to the centre of Chicago, O'Hare International is 26 kilometres from the centre and Greater Rockford is 126 kilometres away from the centre. View on Map.

Book Cheap Chicago Plane Tickets

(Round-trip)
Airports
Origin
Edmonton
C$ 430
only
C$ 430
Montreal
C$ 387
only
C$ 387
Toronto
C$ 270
only
C$ 270
C$ 241
only
C$ 241
Destination
Chicago
C$ 270
only
C$ 270
C$ 241
only
C$ 241
Sat, 9 Feb
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Wed, 13 Feb
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 130 reviews
Boarding
8.0
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: All ok

Cons: Not a thing

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

Fri, 14 Jun
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Sun, 16 Jun
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
C$ 259
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 3 Apr
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
1h 57m
Sun, 7 Apr
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
1h 37m
C$ 270
Trip: 5 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 67 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
YYZ
ORD
Okay 4.6

Pros: Ok

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

YYZ
ORD
Mediocre 2.0

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

YYZ
ORD
Good 6.0

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

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

YYZ
ORD
Excellent 10.0

Pros: It was on time and the staff were excellent

Cons: Like everything

YYZ
ORD
Okay 4.0

Pros: I didn't like nothing

Cons: United needs to training your employees

Fri, 26 Apr
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
1h 49m
Tue, 30 Apr
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
1h 37m
C$ 272
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 212 reviews
Overall
7.2
Boarding
7.4
Comfort
7.1
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
ORD
Excellent 10.0

Cons: Everything was great

YYZ
ORD
Excellent 8.0

Pros: Meh

Cons: Meh

YYZ
ORD
Good 7.0

Pros: The movies on board

Cons: The fact the plane was late

YYZ
ORD
Good 7.0

Pros: Had extra space because plane was not full

Cons: Flight was delayed. Changed gate three times

YYZ
ORD
Mediocre 2.0

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

Wed, 6 Feb
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
4h 50m
Fri, 15 Feb
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
4h 14m
C$ 278
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,517 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LAX
PDX
Mediocre 2.0

Pros: It was ok

Cons: They lost my suitcase. Now I have to wait a day or two and they won’t sent it to me.

JFK
BCN
Excellent 8.6

Pros: Good food, entertainment and Delta Comfort section worth the extra cost.

Cons: Boarding at JFK a nightmare.

MIA
LGA
Excellent 8.3

Pros: Arrived on time and smooth flight though it was completely full

JFK
DUB
Good 6.0

Pros: The flight crew was very competent and welcoming.

Cons: The gate agent at JFK was annoying. She forced us to check carry on bags for no apparent reason. Much larger carry on’s were allowed both before and after us. Her fellow agent seemed like she wanted to apologize for her capricious behavior, but was understandably hesitant to do so. The airplane seating was cramped and uncomfortable. The rntertainment choices were very limited unless you enjoy superhero movies or a very limited range of audio/musical selections. So it goes in coach class.

DCA
LAX
Excellent 9.3

Pros: The plane was very new and clean; entertainment options and food were very good; it was a good flight.

Cons: At baggage drop-DCA: Charged me for a bag when I had a status that allows 1 bag free; she would not listen, made me pay for it in order to check my bag and then told me to go over to customer service and ask for a refund.

Sat, 2 Feb
YUL
Montreal Pierre Elliott Trudeau International
ORD
Chicago O'Hare International
28h 14m
Wed, 6 Feb
ORD
Chicago O'Hare International
YUL
Montreal Pierre Elliott Trudeau International
15h 49m
C$ 387
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 20 Jun
YEG
Edmonton
ORD
Chicago O'Hare International
16h 31m
Mon, 24 Jun
ORD
Chicago O'Hare International
YEG
Edmonton
9h 41m
C$ 430
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 7,563 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.1
Food
7.2
YEG
YVR
Excellent 9.0

Pros: Check in was quick and easy. Boarding and flight was right on time!

PHX
YYZ
Okay 5.3

Pros: Friendly staff; A relatively painless check-in and boarding procedure; Flight arrived a bit earlier than scheduled.

Cons: No power outlet at seat on 4+ hour flight meant dead phone on arrival when used for in-flight entertainment; Now have to pay extra for basic seat selection even after check-in opens at 24-hours prior to departure (I opted not to pay, and got literally the worst seat on the plane... back row, middle seat by the lavatory); Even the for-purchase snacks taste terrible.

YEG
YQU
Excellent 10.0

Pros: West jet always communicates

Cons: Waiting to board.. always a hassle

YVR
PVR
Good 7.6

Cons: Food options are terrible especially when you pay for them. Better quality needed

YYZ
FLL
Mediocre 2.0

Pros: Did not fly!

Sat, 30 Mar
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, 31 Mar
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 2 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 130 reviews
Boarding
8.0
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 10.0

Pros: All ok

Cons: Not a thing

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

Fri, 12 Apr
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Mon, 15 Apr
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 130 reviews
Boarding
8.0
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

Wed, 6 Feb
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
1h 58m
Wed, 13 Feb
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
1h 31m
C$ 272
Trip: 8 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 67 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
YYZ
ORD
Okay 4.0

Pros: I didn't like nothing

Cons: United needs to training your employees

YYZ
ORD
Good 6.3

Pros: Crew was curteous and capable

Cons: 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 10.0

Pros: comfortable and on time

YYZ
ORD
Mediocre 2.0

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

YYZ
ORD
Good 6.0

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

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

Fri, 8 Feb
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
8h 26m
Mon, 11 Feb
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
7h 39m
C$ 278
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,517 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LAX
PDX
Mediocre 2.0

Pros: It was ok

Cons: They lost my suitcase. Now I have to wait a day or two and they won’t sent it to me.

DCA
LAX
Excellent 9.3

Pros: The plane was very new and clean; entertainment options and food were very good; it was a good flight.

Cons: At baggage drop-DCA: Charged me for a bag when I had a status that allows 1 bag free; she would not listen, made me pay for it in order to check my bag and then told me to go over to customer service and ask for a refund.

DEN
JFK
Excellent 9.3

Pros: Staff from Check in to aircraft very pleasant. Snack choice in Coach impressive.

LAX
AMS
Excellent 9.0

Cons: flight was delayed

JFK
BCN
Excellent 8.6

Pros: Good food, entertainment and Delta Comfort section worth the extra cost.

Cons: Boarding at JFK a nightmare.

Thu, 20 Jun
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
1h 48m
Sun, 30 Jun
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
1h 36m
C$ 286
Trip: 11 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 212 reviews
Overall
7.2
Boarding
7.4
Comfort
7.1
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
ORD
Mediocre 2.0

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

YYZ
ORD
Mediocre 2.0

Cons: No more seats, rescheduled for the next day. poor service

YYZ
ORD
Good 7.0

Pros: Had extra space because plane was not full

Cons: Flight was delayed. Changed gate three times

YYZ
ORD
Mediocre 3.6

Pros: The only person who who tried to relax customers waiting to board was the pilot. Flight was delayed. No updates on monitors, no crew at desk. The pilot was first to arrive and had no information but was engaging and joked with all the passengers just standing around. He was our only assurance that flight was still going. He had same attitude on the plane and seemed determined to get us home eventually.

Cons: No communication from airline. The flight was delayed but we only find out because we show up to gate and nobody is there. No counter agents. When they eventually show up, there is no explanation. Just acted like everything was normal.

YYZ
ORD
Good 7.0

Pros: The movies on board

Cons: The fact the plane was late

Fri, 8 Feb
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
1h 58m
Mon, 11 Feb
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
1h 31m
C$ 272
Trip: 4 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 67 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
YYZ
ORD
Excellent 10.0

Pros: It was on time and the staff were excellent

Cons: Like everything

YYZ
ORD
Good 6.0

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

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

YYZ
ORD
Excellent 10.0

Pros: comfortable and on time

YYZ
ORD
Okay 5.3

Pros: Flight was on time and short in duration

Cons: 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

Pros: Nothing

Cons: Everything

Fri, 26 Apr
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Tue, 30 Apr
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 248
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 130 reviews
Boarding
8.0
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

Fri, 1 Mar
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
3h 58m
Mon, 4 Mar
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
7h 30m
C$ 278
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,517 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
JFK
Okay 4.6

Cons: Flying from New York to Atlanta on business class there was no access to the lounge because I was not flying to Lima on the same day. I bought the whole international business ticket to Peru together, I don't understand why Delta consider my first portion not part of my international ticket!

ATL
FLL
Excellent 10.0

Cons: Everything was good!

DEN
JFK
Excellent 9.3

Pros: Staff from Check in to aircraft very pleasant. Snack choice in Coach impressive.

PVR
ATL
Excellent 9.3

Pros: Great entertainment options!

Cons: The seats are still too small. I also wish there were hot options for food.

LAX
AMS
Excellent 9.0

Cons: flight was delayed

Wed, 26 Jun
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
1h 48m
Sun, 30 Jun
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
1h 36m
C$ 286
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 212 reviews
Overall
7.2
Boarding
7.4
Comfort
7.1
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
ORD
Mediocre 2.0

Cons: 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
Mediocre 2.0

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

YYZ
ORD
Mediocre 2.0

Cons: No more seats, rescheduled for the next day. poor service

YYZ
ORD
Good 7.0

Pros: The movies on board

Cons: The fact the plane was late

YYZ
ORD
Okay 4.0

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

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

Fri, 1 Mar
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
7h 06m
Sun, 3 Mar
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
10h 48m
C$ 318
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 1 Mar
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
1h 58m
Sun, 3 Mar
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
1h 35m
C$ 272
Trip: 3 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 67 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
YYZ
ORD
Excellent 10.0

Pros: It was on time and the staff were excellent

Cons: Like everything

YYZ
ORD
Excellent 10.0

Pros: comfortable and on time

YYZ
ORD
Excellent 10.0

Pros: Fantastic service. Much obliged for everything

YYZ
ORD
Okay 5.3

Pros: Flight was on time and short in duration

Cons: 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 4.6

Pros: Ok

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

Fri, 22 Feb
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, 24 Feb
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 249
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 130 reviews
Boarding
8.0
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Pros: All ok

Cons: Not a thing

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Excellent 8.0

Cons: Delay

Fri, 22 Mar
YYZ
Toronto Pearson Intl
ORD
Chicago O'Hare International
4h 07m
Fri, 29 Mar
ORD
Chicago O'Hare International
YYZ
Toronto Pearson Intl
3h 04m
C$ 286
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,499 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
DEN
JFK
Excellent 9.3

Pros: Staff from Check in to aircraft very pleasant. Snack choice in Coach impressive.

ATL
JFK
Okay 4.6

Cons: Flying from New York to Atlanta on business class there was no access to the lounge because I was not flying to Lima on the same day. I bought the whole international business ticket to Peru together, I don't understand why Delta consider my first portion not part of my international ticket!

ATL
FLL
Excellent 10.0

Cons: Everything was good!

JFK
BCN
Excellent 8.6

Pros: Good food, entertainment and Delta Comfort section worth the extra cost.

Cons: Boarding at JFK a nightmare.

LAX
PDX
Mediocre 2.0

Pros: It was ok

Cons: They lost my suitcase. Now I have to wait a day or two and they won’t sent it to me.

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