Find Cheap Flights to Chicago Midway (MDW)

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(Round-trip)
Airports
Origin
Toronto
C$ 262
only
C$ 262
C$ 233
only
C$ 233
Destination
Chicago
C$ 233
only
C$ 233
Sat, 6 Jan
YTZ
MDW
1h 50m
Fri, 12 Jan
MDW
YTZ
1h 37m
C$ 233
Trip: 7 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

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Good 6.0

Efficient

Late flight

Tue, 9 Jan
YYZ
MDW
5h 16m
Fri, 12 Jan
MDW
YYZ
5h 37m
C$ 262
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Thu, 4 Jan
YTZ
MDW
1h 50m
Fri, 12 Jan
MDW
YTZ
1h 37m
C$ 250
Trip: 9 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 10.0

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

YTZ
MDW
Good 6.0

Efficient

Late flight

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

Breakfast, bars, etcnithin

Nada

Thu, 11 Jan
YYZ
MDW
6h 14m
Mon, 15 Jan
MDW
YYZ
4h 31m
C$ 262
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Sun, 7 Jan
YTZ
MDW
1h 50m
Thu, 11 Jan
MDW
YTZ
1h 37m
C$ 250
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
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
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.

Tue, 16 Jan
YYZ
MDW
7h 23m
Sat, 27 Jan
MDW
YYZ
4h 22m
C$ 262
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Tue, 9 Jan
YTZ
MDW
1h 50m
Fri, 12 Jan
MDW
YTZ
1h 37m
C$ 261
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 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
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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.

Wed, 17 Jan
YYZ
MDW
6h 14m
Sat, 27 Jan
MDW
YYZ
4h 22m
C$ 262
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

Thu, 11 Jan
YTZ
MDW
1h 50m
Mon, 15 Jan
MDW
YTZ
1h 37m
C$ 261
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
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

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

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.

Thu, 18 Jan
YYZ
MDW
6h 14m
Sat, 27 Jan
MDW
YYZ
7h 49m
C$ 262
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Fri, 12 Jan
YTZ
MDW
1h 40m
Mon, 15 Jan
MDW
YTZ
1h 37m
C$ 261
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 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

YTZ
MDW
Mediocre 2.0

Nothing

Everything

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 8.0

Polite crew

Would like a sandwich instead of nuts

Sat, 20 Jan
YYZ
MDW
4h 32m
Sat, 27 Jan
MDW
YYZ
4h 22m
C$ 262
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Sat, 13 Jan
YTZ
MDW
1h 50m
Mon, 15 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 3 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 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 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
Mediocre 2.0

Nothing

Everything

Thu, 25 Jan
YYZ
MDW
6h 25m
Sun, 28 Jan
MDW
YYZ
3h 25m
C$ 262
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

Sun, 14 Jan
YTZ
MDW
1h 50m
Mon, 15 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 2 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
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

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Good 6.0

Efficient

Late flight

Fri, 26 Jan
YYZ
MDW
6h 14m
Sun, 28 Jan
MDW
YYZ
3h 25m
C$ 262
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Mon, 15 Jan
YTZ
MDW
1h 50m
Tue, 16 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 2 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 10.0

Good

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Good 6.0

Efficient

Late flight

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

I liked the lounge

There were a lot of people and not enough outlets

Sat, 10 Feb
YYZ
MDW
4h 32m
Mon, 12 Feb
MDW
YYZ
7h 34m
C$ 262
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Tue, 16 Jan
YTZ
MDW
1h 50m
Sun, 28 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 13 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 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

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
Good 6.6

Onboard crew was very nice

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

Tue, 27 Feb
YYZ
MDW
3h 22m
Sat, 10 Mar
MDW
YYZ
3h 17m
C$ 262
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

*
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