Find Cheap Flights from Toronto Pearson Intl to Chicago Midway (YYZ - MDW)

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FAQs for Booking Toronto Pearson Intl to Chicago Midway Flights

How long does a flight from Toronto Pearson Intl to Chicago Midway take?
An average nonstop flight takes 3h 26m, covering a distance of 697 km.
Which airlines provide the cheapest flights from Toronto Pearson Intl to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta (C$ 261)
Do I need a passport to fly between Toronto Pearson Intl and Chicago Midway?
Yes.
What’s the cheapest day of the week to fly from Toronto Pearson Intl to Chicago Midway?
For Toronto Pearson Intl to Chicago Midway, Friday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago Midway back to Toronto Pearson Intl, the best deals are generally found on Thursday, with Friday being the most expensive.

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for C$ 296 or less.

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

Airports
Origin
Toronto
C$ 261
only
C$ 261
Destination
Chicago
C$ 261
only
C$ 261
Fri, 9 Feb
YYZ
MDW
6h 14m
Mon, 12 Feb
MDW
YYZ
7h 28m
C$ 261
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
BWI
Okay 4.6

Snacks & beverages on a 1 hour flight. Very nice crew

Older plane, no entertainment

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

DFW
LGA
Excellent 10.0

Good service, more leg room than American Airlines.

Everything was good.

MEX
ATL
Good 7.0

Beautiful plane, great entertainment system, two bathrooms for economy class, decent food

Thu, 5 Apr
YYZ
MDW
3h 27m
Tue, 17 Apr
MDW
YYZ
3h 57m
C$ 282
Trip: 13 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

DTW
ATL
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

ATL
MBJ
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

Thu, 1 Mar
YYZ
MDW
6h 24m
Fri, 2 Mar
MDW
YYZ
3h 17m
C$ 295
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

DTW
ATL
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

Fri, 2 Feb
YYZ
MDW
8h 35m
Mon, 5 Feb
MDW
YYZ
6h 14m
C$ 314
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

ATL
MBJ
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

Sat, 26 May
YYZ
MDW
4h 02m
Tue, 29 May
MDW
YYZ
7h 24m
C$ 315
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DFW
LGA
Excellent 10.0

Good service, more leg room than American Airlines.

Everything was good.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

DTW
ATL
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

FLL
ATL
Okay 4.6

You had me check my hand luggage with expensive items that did not arrive.

Tue, 17 Jul
YYZ
MDW
6h 05m
Tue, 24 Jul
MDW
YYZ
7h 23m
C$ 337
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

ATL
MBJ
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

FLL
ATL
Okay 4.6

You had me check my hand luggage with expensive items that did not arrive.

DTW
ATL
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

Fri, 26 Jan
YYZ
MDW
6h 13m
Fri, 2 Feb
MDW
YYZ
4h 50m
C$ 376
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MEX
ATL
Good 7.0

Beautiful plane, great entertainment system, two bathrooms for economy class, decent food

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

FLL
ATL
Okay 4.6

You had me check my hand luggage with expensive items that did not arrive.

Thu, 21 Jun
YYZ
MDW
3h 26m
Tue, 26 Jun
MDW
YYZ
4h 20m
C$ 391
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
ATL
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

ATL
MBJ
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

FLL
ATL
Okay 4.6

You had me check my hand luggage with expensive items that did not arrive.

ATL
BWI
Okay 4.6

Snacks & beverages on a 1 hour flight. Very nice crew

Older plane, no entertainment

Tue, 27 Mar
YYZ
MDW
5h 18m
Sat, 31 Mar
MDW
YYZ
4h 16m
C$ 455
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

MEX
ATL
Good 7.0

Beautiful plane, great entertainment system, two bathrooms for economy class, decent food

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

DFW
LGA
Excellent 10.0

Good service, more leg room than American Airlines.

Everything was good.

Thu, 15 Feb
YYZ
MDW
5h 16m
Sun, 18 Feb
MDW
YYZ
3h 58m
C$ 478
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
ATL
Excellent 8.0

I love Delta, especially their newer planes that have screens in the backs of headrests and free movies.

Leg room is never enough. I'm 6'1".

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

FLL
ATL
Okay 4.6

You had me check my hand luggage with expensive items that did not arrive.

JFK
TPA
Good 6.6

We landed earlier than expected

Bathroom was very smelly

Fri, 22 Jun
YYZ
MDW
6h 05m
Mon, 25 Jun
MDW
YYZ
7h 23m
C$ 499
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DFW
LGA
Excellent 10.0

Good service, more leg room than American Airlines.

Everything was good.

MEX
ATL
Good 7.0

Beautiful plane, great entertainment system, two bathrooms for economy class, decent food

FLL
ATL
Okay 4.6

You had me check my hand luggage with expensive items that did not arrive.

LAX
DEN
Excellent 10.0

Excellent piloting and cabin crew.

LGA
PIT
Excellent 10.0

Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!

Toronto Pearson Intl to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Toronto Pearson Intl
Flight Price C$ 261
Distance 697 km
Airlines Delta
*
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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.