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

Airports
Origin
Québec City
$397
only
$397
Vancouver
$294
only
$294
Montreal
$237
only
$237
Toronto
$243
only
$243
$209
only
$209
Destination
Chicago
$209
only
$209
Tue, Apr 17
YTZ
MDW
1h 45m
Thu, Apr 26
MDW
YTZ
1h 40m
Trip: 10 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
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

Delay

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Tue, Mar 27
YYZ
MDW
6h 20m
Wed, Apr 4
MDW
YYZ
4h 55m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
AMS
JFK
Okay 5.6

Food was better than the usual airline food. We also got a Valentine's day chocolate.

seats too narrow, barely have room to sit and stand. No USB charger

LGA
MCI
Excellent 10.0

The service and non stop smooth ride. Boarding was a new experiance taking a bus to the plane. Was quick and crew helpful storing my carryon. Everyone very helpful.

ATL
ALB
Good 6.0

The crew was amazing. They were attentive and very professional

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average. The crew

STL
ATL
Okay 4.6

They changed my flight to a different one departing 2 hours earlier and did not notify me! The original flight was still available & they would not let me take it despite my reservation paper work. CRAZY! I have a two hour drive to the airport this gave me the option to leave home at 2:30am or go the night before and pay for a hotel. Flight was managed by DELTA who also did not care! All involved blamed each other. Beware

CUN
MSP
Excellent 10.0

The flights were on time and they did two drink and snack services. Great crew!

Mon, Mar 26
YQB
MDW
6h 30m
Sat, Mar 31
MDW
YQB
7h 55m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 21
YTZ
MDW
1h 50m
Sun, Mar 25
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
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
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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

Wed, May 23
YTZ
MDW
1h 40m
Mon, Jun 11
MDW
YTZ
1h 40m
Trip: 20 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
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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

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.

Tue, Apr 17
YYZ
MDW
3h 30m
Thu, Apr 19
MDW
YYZ
5h 42m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
ALB
Good 6.0

The crew was amazing. They were attentive and very professional

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average. The crew

CUN
MSP
Excellent 10.0

The flights were on time and they did two drink and snack services. Great crew!

MCI
LGA
Good 6.0

Too crowded overhead storage got filled right away. Had to place my bag under seat. Could not extend my legs.

STL
ATL
Okay 4.6

They changed my flight to a different one departing 2 hours earlier and did not notify me! The original flight was still available & they would not let me take it despite my reservation paper work. CRAZY! I have a two hour drive to the airport this gave me the option to leave home at 2:30am or go the night before and pay for a hotel. Flight was managed by DELTA who also did not care! All involved blamed each other. Beware

AMS
JFK
Okay 5.6

Food was better than the usual airline food. We also got a Valentine's day chocolate.

seats too narrow, barely have room to sit and stand. No USB charger

Fri, Apr 13
YTZ
MDW
1h 45m
Sun, Apr 15
MDW
YTZ
1h 40m
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
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 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 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
Mediocre 2.0

Nothing

Everything

Sun, May 20
YYZ
MDW
6h 15m
Tue, Jun 12
MDW
YYZ
5h 17m
Trip: 24 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
AMS
JFK
Okay 5.6

Food was better than the usual airline food. We also got a Valentine's day chocolate.

seats too narrow, barely have room to sit and stand. No USB charger

CUN
MSP
Excellent 10.0

The flights were on time and they did two drink and snack services. Great crew!

GPT
ATL
Good 6.0

The crew was organized and made us all laugh, and had a great personality.

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average.

DTW
AMS
Good 7.0

The vegan meal was not good

STL
ATL
Okay 4.6

They changed my flight to a different one departing 2 hours earlier and did not notify me! The original flight was still available & they would not let me take it despite my reservation paper work. CRAZY! I have a two hour drive to the airport this gave me the option to leave home at 2:30am or go the night before and pay for a hotel. Flight was managed by DELTA who also did not care! All involved blamed each other. Beware

Mon, Mar 12
YTZ
MDW
1h 50m
Wed, Mar 14
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
Good 6.6

Onboard crew was very nice

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

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 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
Good 6.4

Major delays that were poorly handled.

Tue, Jul 31
YYZ
MDW
4h 54m
Tue, Aug 7
MDW
YYZ
6h 08m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
AMS
JFK
Okay 5.6

Food was better than the usual airline food. We also got a Valentine's day chocolate.

seats too narrow, barely have room to sit and stand. No USB charger

ATL
EYW
Excellent 8.6

Once we hit the coast we skirted down the coas of Florida which provided a spectacular view. The approach and landing at Key West airport was thrilling and absolutely perfect. We’ve flown Delta many times but this was our first but not last time to Key West.

Nothing

MSP
MZT
Mediocre 2.0

The flight was a Christmas gift for my mother to spend some time with her friends in Mazatlán. I heard she spent the entire day waiting at the airport as her flight was rescheduled 4 times.

STL
ATL
Okay 4.6

They changed my flight to a different one departing 2 hours earlier and did not notify me! The original flight was still available & they would not let me take it despite my reservation paper work. CRAZY! I have a two hour drive to the airport this gave me the option to leave home at 2:30am or go the night before and pay for a hotel. Flight was managed by DELTA who also did not care! All involved blamed each other. Beware

OKC
DTW
Excellent 10.0

As usual

Landing was a bit rough

Fri, Jun 15
YTZ
MDW
1h 45m
Mon, Jun 18
MDW
YTZ
1h 40m
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 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

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

Wed, Mar 28
YTZ
MDW
1h 50m
Tue, Apr 3
MDW
YTZ
1h 37m
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
Excellent 8.3

fast

no TSA precheck

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
Excellent 10.0

Good

YTZ
MDW
Good 6.0

Efficient

Late flight

Wed, Mar 28
YYZ
MDW
3h 47m
Tue, Apr 3
MDW
YYZ
5h 26m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
AMS
JFK
Okay 5.6

Food was better than the usual airline food. We also got a Valentine's day chocolate.

seats too narrow, barely have room to sit and stand. No USB charger

GPT
ATL
Good 6.0

The crew was organized and made us all laugh, and had a great personality.

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average.

ATL
EYW
Excellent 8.6

Once we hit the coast we skirted down the coas of Florida which provided a spectacular view. The approach and landing at Key West airport was thrilling and absolutely perfect. We’ve flown Delta many times but this was our first but not last time to Key West.

Nothing

CUN
MSP
Excellent 10.0

The flights were on time and they did two drink and snack services. Great crew!

DTW
AMS
Good 7.0

The vegan meal was not good

Fri, Jun 1
YTZ
MDW
1h 45m
Sat, Jun 2
MDW
YTZ
1h 40m
Trip: 2 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 8.0

Delay

YTZ
MDW
Excellent 10.0

Good

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 6.6

Onboard crew was very nice

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

Tue, Apr 3
YYZ
MDW
6h 15m
Thu, Apr 5
MDW
YYZ
3h 42m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
EYW
Excellent 8.6

Once we hit the coast we skirted down the coas of Florida which provided a spectacular view. The approach and landing at Key West airport was thrilling and absolutely perfect. We’ve flown Delta many times but this was our first but not last time to Key West.

Nothing

LGA
MCI
Excellent 10.0

The service and non stop smooth ride. Boarding was a new experiance taking a bus to the plane. Was quick and crew helpful storing my carryon. Everyone very helpful.

DTW
AMS
Good 7.0

The vegan meal was not good

MSP
MZT
Mediocre 2.0

The flight was a Christmas gift for my mother to spend some time with her friends in Mazatlán. I heard she spent the entire day waiting at the airport as her flight was rescheduled 4 times.

CUN
MSP
Excellent 10.0

The flights were on time and they did two drink and snack services. Great crew!

Sat, Jun 23
YUL
MDW
3h 30m
Wed, Jun 27
MDW
YUL
5h 55m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1810 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
BOS
YTZ
Excellent 10.0

Prompt service and proximity of airport to the city. We literally walked to our hotel

YOW
YTZ
Good 6.6

I could not believe that the wine and beer were free

I did not like the landing. Too much delay and I was concerned that I might have missed my next flight to Newark

BOS
YTZ
Good 6.3

Interior noise from plane is annoying

YTZ
YOW
Excellent 8.6

The check in process was very easy. The boarding process was very easy. The flight attendants were very pleasant.

There was not anything to complain about.

YTZ
IAD
Excellent 8.3

the snack (chips) I recieved was expired and had a smell to it!

Wed, Apr 4
YVR
MDW
8h 14m
Wed, Apr 11
MDW
YVR
11h 16m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GPT
ATL
Good 6.0

The crew was organized and made us all laugh, and had a great personality.

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average.

OKC
DTW
Excellent 10.0

As usual

Landing was a bit rough

ATL
ALB
Good 6.0

The crew was amazing. They were attentive and very professional

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average. The crew

MSP
MZT
Mediocre 2.0

The flight was a Christmas gift for my mother to spend some time with her friends in Mazatlán. I heard she spent the entire day waiting at the airport as her flight was rescheduled 4 times.

STL
ATL
Okay 4.6

They changed my flight to a different one departing 2 hours earlier and did not notify me! The original flight was still available & they would not let me take it despite my reservation paper work. CRAZY! I have a two hour drive to the airport this gave me the option to leave home at 2:30am or go the night before and pay for a hotel. Flight was managed by DELTA who also did not care! All involved blamed each other. Beware

Sun, Mar 11
YUL
MDW
6h 04m
Tue, Mar 13
MDW
YUL
6h 10m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1810 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
BOS
Excellent 10.0

The Porter Lounge is so nice

BOS
YTZ
Good 6.3

Interior noise from plane is annoying

YTZ
YUL
Excellent 10.0

I appreciated how the staff took me in a wheet-chair all the way to the customs and waited with me while they checked me out. they were courteous, kind and genuine.Very refreshing in this day and age. God Bless all the staff at Porter Air Lines. thank you so very very much, Barbara Ann MacMahon-Firestone, Toronto,Ontario.

YTZ
BOS
Excellent 8.0

Arriving and calling someone to help me with the wheelchair was good. The women were so friendly and helpful. But when you're "stuck" in a chair and I arrived early, it would be nice for someone to check to see if you had to go the washroom. And I had to flag someone down to get me to the aircraft. No one came by and offered. But overall fantastic experience. I would fly porter again.

Wish their was more food on the flight. Even though it was a short one.

YOW
YTZ
Good 6.6

I could not believe that the wine and beer were free

I did not like the landing. Too much delay and I was concerned that I might have missed my next flight to Newark

Fri, Jun 15
YYZ
MDW
6h 05m
Mon, Jun 18
MDW
YYZ
5h 17m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16046 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GPT
ATL
Good 6.0

The crew was organized and made us all laugh, and had a great personality.

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average.

MSP
MZT
Mediocre 2.0

The flight was a Christmas gift for my mother to spend some time with her friends in Mazatlán. I heard she spent the entire day waiting at the airport as her flight was rescheduled 4 times.

AMS
PDX
Mediocre 3.0

NOTHING

ATL
ALB
Good 6.0

The crew was amazing. They were attentive and very professional

I upgraded my seat and paid extra for one with more room. And I wasn’t impressed with my upgrade, doesn’t feel like more leg than regular seats. Comfort was below average. The crew

STL
ATL
Okay 4.6

They changed my flight to a different one departing 2 hours earlier and did not notify me! The original flight was still available & they would not let me take it despite my reservation paper work. CRAZY! I have a two hour drive to the airport this gave me the option to leave home at 2:30am or go the night before and pay for a hotel. Flight was managed by DELTA who also did not care! All involved blamed each other. Beware

Sat, Apr 28
YUL
MDW
4h 00m
Wed, May 2
MDW
YUL
5h 10m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1810 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YOW
YTZ
Good 6.6

I could not believe that the wine and beer were free

I did not like the landing. Too much delay and I was concerned that I might have missed my next flight to Newark

YTZ
EWR
Good 7.6

The waiting lounge was nice and complemented with refreshments

When I got to Toronto I was directed to the wrong lounge for a while before I asked and was redirected to the correct lounge

YTZ
IAD
Good 6.0

The cabin crew provided the most information out of the entire experience and were extremely friendly. I appreciate Dawn in particular. The lounge is nice when it is not so over-crowded. I appreciate some complimentary minor snacks and drinks; it certainly helped with the delay. What would normally be sufficient seating and power outlets became people tripping over each other with delayed flights.

The lounge staff were hard to find and not communicative about delays. The board only had 1 update to my departure time, which was 30 mins after the originally scheduled time, and did not update again until 25 minutes after that second time had passed. The lounge staff did not make an announcement until after that board update and even then the information was wrong. The one time I found someone to ask a question to, I was given the same information. I had no idea why there was a delay or what to expect and no way of finding out. It made coordinating next steps upon my arrival to my destination extremely difficult. The lounge is not particularly well-equipped for multiple delayed flights.

YTZ
YOW
Excellent 8.6

The check in process was very easy. The boarding process was very easy. The flight attendants were very pleasant.

There was not anything to complain about.

YQG
YTZ
Excellent 8.6

The check in process was very easy. The boarding process was very easy. The flight attendants were very pleasant.

There was not anything to complain about.

Canada to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Canada
Flight Price $209
Airlines Porter Airlines, Delta
*
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