Find Cheap Flights from Ontario to Chicago Midway

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

Airports
Origin
Ottawa
C$ 311
only
C$ 311
Toronto
C$ 263
only
C$ 263
C$ 251
only
C$ 251
Destination
Chicago
C$ 251
only
C$ 251
Thu, 4 Jan
YTZ
MDW
1h 50m
Mon, 8 Jan
MDW
YTZ
1h 37m
C$ 251
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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

Good

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.

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.

Sat, 20 Jan
YYZ
MDW
4h 32m
Tue, 23 Jan
MDW
YYZ
6h 36m
C$ 263
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

LGA
YUL
Excellent 8.0

it was easy to navigate .

Thu, 1 Feb
YTZ
MDW
1h 50m
Sun, 4 Feb
MDW
YTZ
1h 37m
C$ 262
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Fri, 26 Jan
YYZ
MDW
6h 14m
Sun, 28 Jan
MDW
YYZ
3h 25m
C$ 263
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

LGA
YUL
Excellent 8.0

it was easy to navigate .

SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

Fri, 2 Mar
YTZ
MDW
1h 50m
Wed, 7 Mar
MDW
YTZ
1h 37m
C$ 262
Trip: 6 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Thu, 1 Feb
YYZ
MDW
6h 25m
Sat, 3 Feb
MDW
YYZ
5h 53m
C$ 263
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

LGA
YUL
Excellent 8.0

it was easy to navigate .

Thu, 5 Apr
YTZ
MDW
1h 50m
Mon, 9 Apr
MDW
YTZ
1h 37m
C$ 262
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
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
Good 6.6

Onboard crew was very nice

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

Thu, 1 Mar
YYZ
MDW
3h 22m
Tue, 6 Mar
MDW
YYZ
4h 23m
C$ 263
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

Sat, 20 Jan
YTZ
MDW
1h 50m
Tue, 23 Jan
MDW
YTZ
1h 37m
C$ 274
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
Excellent 8.0

Breakfast, bars, etcnithin

Nada

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 10.0

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

Sun, 25 Mar
YTZ
MDW
1h 50m
Thu, 29 Mar
MDW
YTZ
1h 37m
C$ 274
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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 8.3

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 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

Sat, 9 Jun
YYZ
MDW
6h 10m
Sat, 16 Jun
MDW
YYZ
5h 19m
C$ 320
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

LGA
YUL
Excellent 8.0

it was easy to navigate .

Fri, 1 Jun
YTZ
MDW
1h 45m
Mon, 4 Jun
MDW
YTZ
1h 40m
C$ 285
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

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

Wed, 11 Apr
YYZ
MDW
5h 07m
Tue, 24 Apr
MDW
YYZ
4h 57m
C$ 334
Trip: 14 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

Wed, 24 Jan
YOW
MDW
3h 30m
Mon, 29 Jan
MDW
YOW
5h 38m
C$ 311
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
IAD
YTZ
Excellent 10.0

Porter Airline was amazing!! They use glasses instead of plastic cups! Nice, cheap, on time, and free wine!

YOW
YTZ
Excellent 10.0

On time. Provided snacks and drinks even on a short flight. Group lobby prior to boarding provided coffee, tea, snacks, water for free.

YUL
YTZ
Okay 5.6

The service was great and fast

Both of my Porter Airlines flights were delayed. It seems they often delay / cancel flights

YTZ
IAD
Excellent 10.0

Smaller gate lounge area with lots of private space and complimentary drinks and snack. All Porter employees that I had interaction were professional and attentive to my needs

No suggestion

YTZ
EWR
Excellent 10.0

as above

Wed, 27 Dec
YTZ
MDW
1h 50m
Sun, 31 Dec
MDW
YTZ
1h 37m
C$ 314
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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 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
Good 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 10.0

Good

Sun, 25 Mar
YYZ
MDW
6h 15m
Thu, 29 Mar
MDW
YYZ
4h 23m
C$ 393
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

Sat, 30 Dec
YTZ
MDW
1h 50m
Thu, 4 Jan
MDW
YTZ
1h 37m
C$ 319
Trip: 6 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Good

Mon, 18 Jun
YYZ
MDW
6h 33m
Wed, 20 Jun
MDW
YYZ
4h 20m
C$ 409
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

LGA
YUL
Excellent 8.0

it was easy to navigate .

Thu, 10 May
YOW
MDW
3h 20m
Mon, 14 May
MDW
YOW
4h 33m
C$ 326
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
EWR
Excellent 10.0

as above

YTZ
BOS
Excellent 10.0

Great service. Efficient.

YTZ
EWR
Okay 4.0

Delayed twice. No compensation for delays that resulted in hotel cancellations.

IAD
YTZ
Excellent 8.0

Fast check in and customs lines in both airports

The chips are pretty bland. I appreciate the free refreshments, but would like a bit of choice

YTZ
IAD
Excellent 10.0

Smaller gate lounge area with lots of private space and complimentary drinks and snack. All Porter employees that I had interaction were professional and attentive to my needs

No suggestion

Sat, 30 Dec
YTZ
MDW
1h 50m
Tue, 2 Jan
MDW
YTZ
1h 37m
C$ 341
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

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
Excellent 10.0

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

*
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