Find Cheap Flights from Toronto to Chicago Midway (YTO - MDW)

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Sat 16/12
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Good to Know

Average price:
C$ 410
(avg. price over the last 2 weeks)
Good Deal:
C$ 297
or less (round trip)

When to Book Flights from Toronto to Chicago Midway

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for C$ 297 or less.
The cheapest flight from Toronto to Chicago Midway was found, on average, 53 days before departure.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 23% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Toronto to Chicago Midway Flights

How long does a flight from Toronto to Chicago Midway take?
An average nonstop flight takes 1h 45m, covering a distance of 715 km.
How many flights are there between Toronto and Chicago Midway?
There are 79 (nonstop) flights between Toronto and Chicago Midway per week, averaging 11 per day.
Which airlines provide the cheapest flights from Toronto to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines (C$ 250) and Delta (C$ 263)
Do I need a passport to fly between Toronto and Chicago Midway?
Yes.
Which airlines fly most frequently between Toronto and Chicago Midway?
Porter Airlines (11 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from Toronto to Chicago Midway?
For Toronto to Chicago Midway, Thursday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway back to Toronto, the best deals are generally found on Thursday, with Sunday being the most expensive.

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

Airports
Origin
Toronto
C$ 263
only
C$ 263
C$ 250
only
C$ 250
Destination
Chicago
C$ 250
only
C$ 250
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 8.3

fast

no TSA precheck

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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

Tue, 9 Jan
YYZ
MDW
5h 16m
Fri, 12 Jan
MDW
YYZ
5h 37m
C$ 263
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
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.

JFK
YYZ
Excellent 10.0

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

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.

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.

Wed, 7 Feb
YTZ
MDW
1h 50m
Sun, 11 Feb
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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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 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

Breakfast, bars, etcnithin

Nada

Fri, 26 Jan
YYZ
MDW
6h 25m
Fri, 2 Feb
MDW
YYZ
3h 25m
C$ 264
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
JFK
MIA
Okay 5.3

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

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

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.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

Wed, 14 Mar
YTZ
MDW
1h 50m
Mon, 19 Mar
MDW
YTZ
1h 37m
C$ 261
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 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

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.

Thu, 22 Mar
YYZ
MDW
6h 15m
Tue, 27 Mar
MDW
YYZ
4h 44m
C$ 264
Trip: 6 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.

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.

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.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

GSO
ATL
Excellent 10.0

Plane nice and comfortable

Fri, 13 Apr
YTZ
MDW
1h 45m
Fri, 20 Apr
MDW
YTZ
1h 40m
C$ 261
Trip: 8 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
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.

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Good 6.0

Efficient

Late flight

Tue, 6 Feb
YYZ
MDW
6h 14m
Tue, 20 Feb
MDW
YYZ
7h 24m
C$ 286
Trip: 15 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.

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.

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.

JFK
YYZ
Excellent 10.0

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

JFK
MIA
Okay 5.3

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

Tue, 1 May
YTZ
MDW
1h 45m
Fri, 4 May
MDW
YTZ
1h 40m
C$ 281
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
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Good

Thu, 4 Jan
YTZ
MDW
1h 50m
Sun, 7 Jan
MDW
YTZ
1h 37m
C$ 283
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

Polite crew

Would like a sandwich instead of nuts

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

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
Good 6.0

Efficient

Late flight

Tue, 1 May
YYZ
MDW
5h 47m
Fri, 4 May
MDW
YYZ
4h 28m
C$ 340
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
JFK
MIA
Okay 5.3

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

JFK
YYZ
Excellent 10.0

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

GSO
ATL
Excellent 10.0

Plane nice and comfortable

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.

Sun, 1 Apr
YTZ
MDW
1h 50m
Sat, 7 Apr
MDW
YTZ
1h 37m
C$ 297
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
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 6.0

Efficient

Late flight

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

Tue, 17 Apr
YYZ
MDW
6h 17m
Thu, 26 Apr
MDW
YYZ
4h 44m
C$ 365
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
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

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.

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.

Sat, 30 Dec
YTZ
MDW
1h 50m
Mon, 1 Jan
MDW
YTZ
1h 37m
C$ 360
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 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.

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Good 6.0

Efficient

Late flight

Sat, 23 Jun
YYZ
MDW
4h 00m
Wed, 27 Jun
MDW
YYZ
4h 20m
C$ 398
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
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.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

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.

JFK
MIA
Okay 5.3

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

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.

Sun, 1 Apr
YYZ
MDW
6h 15m
Sat, 7 Apr
MDW
YYZ
3h 42m
C$ 409
Trip: 7 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
YYZ
Excellent 10.0

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

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.

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.

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.

Mon, 25 Dec
YTZ
MDW
1h 50m
Sun, 31 Dec
MDW
YTZ
1h 37m
C$ 400
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
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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 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

Thu, 7 Jun
YYZ
MDW
6h 15m
Mon, 11 Jun
MDW
YYZ
5h 00m
C$ 424
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
SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

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.

JFK
MIA
Okay 5.3

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

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.

Fri, 29 Dec
YTZ
MDW
1h 50m
Tue, 2 Jan
MDW
YTZ
1h 37m
C$ 436
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 8.3

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 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

Sun, 17 Dec
YYZ
MDW
6h 17m
Sun, 24 Dec
MDW
YYZ
5h 17m
C$ 541
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
JFK
MIA
Okay 5.3

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

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.

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.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

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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