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

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Good to Know

Average Price:
$270
(avg. price over the last 2 weeks)
Good Deal:
$200
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 $200 or less.
The cheapest flight from Toronto to Chicago Midway was found 53 days before departure, on average.
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 40m, covering a distance of 444 miles.
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 ($195) and Delta ($206)
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 Toronto to Chicago Midway?
For Toronto to Chicago Midway, Thursday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago Midway back to Toronto, the best deals are generally found on Friday, with Thursday being the most expensive.

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

Airports
Origin
Toronto
$206
only
$206
$195
only
$195
Destination
Chicago
$195
only
$195
Thu, Jan 4
YTZ
MDW
1h 50m
Fri, Jan 12
MDW
YTZ
1h 37m
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
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.

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

Sat, Jan 13
YYZ
MDW
4h 32m
Tue, Jan 16
MDW
YYZ
5h 52m
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
DTW
BNA
Mediocre 2.0

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

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

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
YYZ
Excellent 10.0

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

Thu, Feb 1
YTZ
MDW
1h 40m
Thu, Feb 22
MDW
YTZ
1h 37m
Trip: 22 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 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 10.0

Good

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

Fri, Jan 26
YYZ
MDW
6h 25m
Fri, Feb 2
MDW
YYZ
3h 25m
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
YYZ
Excellent 10.0

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

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.

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.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

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

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Sat, Mar 3
YYZ
MDW
3h 27m
Thu, Mar 8
MDW
YYZ
4h 23m
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
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.

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

DTW
BNA
Mediocre 2.0

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

JFK
MIA
Okay 5.3

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

Sat, Apr 7
YTZ
MDW
1h 50m
Mon, Apr 9
MDW
YTZ
1h 37m
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
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.

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

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

Good

Tue, Feb 6
YYZ
MDW
6h 14m
Tue, Feb 20
MDW
YYZ
7h 24m
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
JFK
MIA
Okay 5.3

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

GSO
ATL
Excellent 10.0

Plane nice and comfortable

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

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

JFK
YYZ
Excellent 10.0

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

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

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Good

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

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

Tue, Apr 17
YYZ
MDW
6h 15m
Wed, Apr 18
MDW
YYZ
6h 15m
Trip: 2 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

JFK
YYZ
Excellent 10.0

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

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.

Fri, May 18
YTZ
MDW
1h 45m
Mon, May 21
MDW
YTZ
1h 40m
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 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
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

Sat, May 19
YTZ
MDW
1h 45m
Mon, May 21
MDW
YTZ
1h 40m
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
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
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.

Sun, Dec 31
YTZ
MDW
1h 50m
Fri, Jan 5
MDW
YTZ
1h 37m
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
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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
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

I liked the lounge

There were a lot of people and not enough outlets

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

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

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.

DTW
BNA
Mediocre 2.0

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

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.

Fri, Dec 29
YTZ
MDW
1h 50m
Tue, Jan 2
MDW
YTZ
1h 37m
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
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 8.0

Polite crew

Would like a sandwich instead of nuts

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

Fri, May 4
YYZ
MDW
6h 15m
Tue, May 8
MDW
YYZ
5h 14m
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
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.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

DTW
BNA
Mediocre 2.0

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

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, Jun 7
YYZ
MDW
6h 15m
Mon, Jun 11
MDW
YYZ
5h 00m
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
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.

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.

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

Sat, Dec 30
YTZ
MDW
1h 50m
Mon, Jan 1
MDW
YTZ
1h 37m
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
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Mediocre 2.0

Nothing

Everything

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.

Wed, Dec 20
YYZ
MDW
6h 47m
Sun, Dec 24
MDW
YYZ
7h 04m
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
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

JFK
YYZ
Excellent 10.0

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

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.

JFK
MIA
Okay 5.3

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

Sat, May 19
YYZ
MDW
4h 45m
Mon, May 21
MDW
YYZ
4h 57m
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

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

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.

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.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.