Find Cheap Flights to Chicago Midway (MDW)

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Canada to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Canada
Flight Price C$ 260
Airlines Porter Airlines, Delta

Top Tips for Finding Cheap Flights to Chicago Midway

Looking for cheap airfare to Chicago Midway? 25% of our users found round-trip tickets to Chicago Midway for the following prices or less: From Toronto C$ 341, from Montreal C$ 366
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be January, February and December. The cheapest month to fly to Chicago Midway is January.
Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway flight deals.

FAQs - Booking Chicago Midway flights

How long is the flight to Chicago Midway?

Flights from Toronto 1h 44m

What is the cheapest flight to Chicago Midway?

The cheapest airline ticket to Chicago Midway from Canada in the last 72 hours was C$ 260 round-trip on the route Toronto to Chicago Midway. The most popular route is Toronto to Chicago Midway and the cheapest ticket found on this route in the last 72 hours was C$ 556 round-trip.

Which airlines fly to Chicago Midway?

In general from Canada, Porter Airlines flies the most to Chicago Midway. The most popular route is from Toronto, and Porter Airlines flies this route the most.

How far is Chicago Midway Airport from central Chicago?

Midway Airport is 15 kilometres from the centre of Chicago. View on Map.

Book Cheap Chicago Midway Plane Tickets

(Round-trip)
Airports
Origin
Vancouver
C$ 396
only
C$ 396
Montreal
C$ 301
only
C$ 301
Toronto
C$ 342
only
C$ 342
C$ 260
only
C$ 260
Destination
Chicago
C$ 260
only
C$ 260
Wed, 15 Aug
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Mon, 20 Aug
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
C$ 260
Trip: 6 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 107 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
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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Wed, 12 Dec
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
5h 47m
Sun, 16 Dec
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
4h 56m
C$ 342
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SLC
OAK
Okay 5.6

Left 30 minutes late from SLC.

SFO
JFK
Okay 4.3

Call center tried moving us to later flight that was also delayed by 3 hrs despite telling us it was on time. Fortunately a gate agent moved us back to orig flight

OKC
ATL
Excellent 10.0

Service, service, service!

LHR
SLC
Good 7.6

One of the older male flight attendants was not polite. Got a ride, short response when asking him for anything.

MSP
SFO
Excellent 10.0

Everything went smoothly - very happy

Fri, 14 Sep
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Sun, 16 Sep
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
C$ 268
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 107 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 6.0

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 8.3

fast

no TSA precheck

Thu, 18 Oct
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Mon, 22 Oct
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
C$ 275
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 107 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 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 8.0

Delay

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Okay 4.0

Got to Billy Bishop, only to find out flight is delayed 2 hours.

Fri, 12 Oct
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Mon, 15 Oct
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
C$ 276
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 107 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

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 8.0

Delay

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 9.6

Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

Wed, 29 Aug
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
3h 24m
Sat, 8 Sep
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
10h 07m
C$ 355
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
OKC
ATL
Excellent 10.0

Service, service, service!

CUN
TPA
Excellent 8.6

Service is excellent. And the comfort too.

A couple of rude passengers that were complaining for everything and I felt Delta crew had to be a little more strict with that situation specially when other customers want to have a comfortable and pleasant flight .

LHR
SLC
Good 7.6

One of the older male flight attendants was not polite. Got a ride, short response when asking him for anything.

SLC
LAS
Good 6.0

The landing was somewhat frightening.

JFK
BRU
Excellent 9.0

The Dutch flight attendant who took care of our economy side of the flight was personable, helpful, and cheerful. She made the flight definitely more pleasant because as you know, traveling overseas in economy is no picnic!

Fri, 2 Nov
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, 4 Nov
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 276
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 107 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 9.6

Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

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

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Wed, 5 Sep
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
7h 00m
Sat, 8 Sep
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
8h 46m
C$ 359
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SFO
JFK
Okay 4.3

Call center tried moving us to later flight that was also delayed by 3 hrs despite telling us it was on time. Fortunately a gate agent moved us back to orig flight

KEF
MSP
Excellent 10.0

Everything was perfect and most of all ON TIME Thank you Delta!

LAN
MSP
Mediocre 2.0

Nothing

Platinum member. Flying with gold colleague. He was upgraded. I was 1 on the list, wirh 3 openings. Asked gate agent, and she said just take my seat. Asked attendant, she said same. So spent flight in last seat in back next to bathroom, while 2 comfort + seats were empty. Did not feel like a valued customer.

JFK
BRU
Excellent 9.0

The Dutch flight attendant who took care of our economy side of the flight was personable, helpful, and cheerful. She made the flight definitely more pleasant because as you know, traveling overseas in economy is no picnic!

CUN
TPA
Excellent 8.6

Service is excellent. And the comfort too.

A couple of rude passengers that were complaining for everything and I felt Delta crew had to be a little more strict with that situation specially when other customers want to have a comfortable and pleasant flight .

Thu, 16 Aug
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Mon, 20 Aug
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
C$ 289
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 107 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Okay 4.0

Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

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

Tue, 30 Oct
YVR
Vancouver Intl
MDW
Chicago Midway
8h 40m
Sat, 3 Nov
MDW
Chicago Midway
YVR
Vancouver Intl
6h 03m
C$ 396
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SLC
OAK
Okay 5.6

Left 30 minutes late from SLC.

LAN
MSP
Mediocre 2.0

Nothing

Platinum member. Flying with gold colleague. He was upgraded. I was 1 on the list, wirh 3 openings. Asked gate agent, and she said just take my seat. Asked attendant, she said same. So spent flight in last seat in back next to bathroom, while 2 comfort + seats were empty. Did not feel like a valued customer.

SFO
JFK
Okay 4.3

Call center tried moving us to later flight that was also delayed by 3 hrs despite telling us it was on time. Fortunately a gate agent moved us back to orig flight

LHR
SLC
Good 7.6

One of the older male flight attendants was not polite. Got a ride, short response when asking him for anything.

SLC
LAS
Good 6.0

The landing was somewhat frightening.

Thu, 20 Sep
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Sun, 23 Sep
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
C$ 300
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 107 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
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 6.4

Major delays that were poorly handled.

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.

Sat, 15 Dec
YVR
Vancouver Intl
MDW
Chicago Midway
8h 52m
Thu, 10 Jan
MDW
Chicago Midway
YVR
Vancouver Intl
10h 43m
C$ 396
Trip: 27 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSY
SLC
Excellent 10.0

Great services ce.

LHR
SLC
Good 7.6

One of the older male flight attendants was not polite. Got a ride, short response when asking him for anything.

JFK
BRU
Excellent 9.0

The Dutch flight attendant who took care of our economy side of the flight was personable, helpful, and cheerful. She made the flight definitely more pleasant because as you know, traveling overseas in economy is no picnic!

MSP
SFO
Excellent 10.0

Everything went smoothly - very happy

ATL
COS
Excellent 10.0

The flight attendants gave great service

Fri, 7 Sep
YUL
Montreal Pierre Elliott Trudeau International
MDW
Chicago Midway
4h 27m
Sun, 16 Sep
MDW
Chicago Midway
YUL
Montreal Pierre Elliott Trudeau International
4h 10m
C$ 301
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1,982 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
BOS
Mediocre 2.0

Nice snacks and espresso in lounge in Toronto

Flight was delayed 5 hours due to heat and not good communication to passengers about flight status - plane was tiny. Landing was bumpy. also lounge in Toronto was over crowded

YOW
YTZ
Excellent 10.0

Efficient, punctual, polite and reliable

YTZ
BOS
Mediocre 3.6

once we took off it was okay.

all the delay due to airport issues, thunderstorms, timing of plan landing slots. could have comped us snacks or something for waiting multiple hours and missing dinner time, didn't get compensated in any way for inconvenience

YTZ
BOS
Okay 5.0

Every flight was delayed at least 30 minutes and the boarding and deplannaning process was close to a third-world country airline. Terrible.

YTZ
IAD
Excellent 10.0

The convenience at YTZ airport.

The lack of personnel at the Porter counters at Dulles. Even though I had paid for luggage online and checked in I still had to wait in line for a very long time. There should be a separate line for pre check ins and no carry on.

Fri, 26 Oct
YUL
Montreal Pierre Elliott Trudeau International
MDW
Chicago Midway
4h 27m
Tue, 30 Oct
MDW
Chicago Midway
YUL
Montreal Pierre Elliott Trudeau International
4h 00m
C$ 302
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1,982 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
EWR
Excellent 10.0

Efficient, punctual, polite and reliable

YTZ
BOS
Mediocre 2.0

4:30 flight delayed and then cancelled around 6. I booked the 8:30 flight on my own because they automatically put everyone on the next day's flight without consulting us. The 8:30 flight too was delayed and we boarded the plane at 9:45. The we were asked to deplane. They made us board a different flight at 10:45. These people should not be running an airline--it is dangerous! And what a nightmare!

YOW
YTZ
Excellent 10.0

Efficient, punctual, polite and reliable

YTZ
BOS
Mediocre 2.0

Nice snacks and espresso in lounge in Toronto

Flight was delayed 5 hours due to heat and not good communication to passengers about flight status - plane was tiny. Landing was bumpy. also lounge in Toronto was over crowded

EWR
YTZ
Excellent 8.0

Flight took off 30 min late

Tue, 11 Sep
YVR
Vancouver Intl
MDW
Chicago Midway
11h 17m
Sat, 22 Sep
MDW
Chicago Midway
YVR
Vancouver Intl
7h 41m
C$ 404
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SFO
JFK
Okay 4.3

Call center tried moving us to later flight that was also delayed by 3 hrs despite telling us it was on time. Fortunately a gate agent moved us back to orig flight

ATL
COS
Excellent 10.0

The flight attendants gave great service

KEF
MSP
Excellent 10.0

Everything was perfect and most of all ON TIME Thank you Delta!

MSY
SLC
Excellent 10.0

Great services ce.

CUN
TPA
Excellent 8.6

Service is excellent. And the comfort too.

A couple of rude passengers that were complaining for everything and I felt Delta crew had to be a little more strict with that situation specially when other customers want to have a comfortable and pleasant flight .

Sat, 27 Oct
YYZ
Toronto Pearson Intl
MDW
Chicago Midway
4h 16m
Mon, 29 Oct
MDW
Chicago Midway
YYZ
Toronto Pearson Intl
3h 23m
C$ 412
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSY
SLC
Excellent 10.0

Great services ce.

LAN
MSP
Mediocre 2.0

Nothing

Platinum member. Flying with gold colleague. He was upgraded. I was 1 on the list, wirh 3 openings. Asked gate agent, and she said just take my seat. Asked attendant, she said same. So spent flight in last seat in back next to bathroom, while 2 comfort + seats were empty. Did not feel like a valued customer.

MSP
SFO
Excellent 10.0

Everything went smoothly - very happy

KEF
MSP
Excellent 10.0

Everything was perfect and most of all ON TIME Thank you Delta!

LHR
SLC
Good 7.6

One of the older male flight attendants was not polite. Got a ride, short response when asking him for anything.

Fri, 21 Sep
YUL
Montreal Pierre Elliott Trudeau International
MDW
Chicago Midway
6h 47m
Wed, 26 Sep
MDW
Chicago Midway
YUL
Montreal Pierre Elliott Trudeau International
4h 10m
C$ 312
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1,982 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
BOS
Mediocre 3.6

once we took off it was okay.

all the delay due to airport issues, thunderstorms, timing of plan landing slots. could have comped us snacks or something for waiting multiple hours and missing dinner time, didn't get compensated in any way for inconvenience

YOW
YTZ
Excellent 10.0

Efficient, punctual, polite and reliable

EWR
YTZ
Excellent 8.0

Flight took off 30 min late

YTZ
EWR
Excellent 10.0

Efficient, punctual, polite and reliable

YTZ
BOS
Mediocre 2.0

Nice snacks and espresso in lounge in Toronto

Flight was delayed 5 hours due to heat and not good communication to passengers about flight status - plane was tiny. Landing was bumpy. also lounge in Toronto was over crowded

Sat, 13 Oct
YUL
Montreal Pierre Elliott Trudeau International
MDW
Chicago Midway
4h 57m
Tue, 16 Oct
MDW
Chicago Midway
YUL
Montreal Pierre Elliott Trudeau International
4h 40m
C$ 317
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1,982 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
IAD
YTZ
Mediocre 2.0

Delays! Delays!

YTZ
EWR
Excellent 9.3

Snacks and drink were provided, even on a short trip

I had a window seat, and the side protrudes towards the bottom amongst the inside, so I had less space on my window side

YTZ
BOS
Mediocre 2.0

4:30 flight delayed and then cancelled around 6. I booked the 8:30 flight on my own because they automatically put everyone on the next day's flight without consulting us. The 8:30 flight too was delayed and we boarded the plane at 9:45. The we were asked to deplane. They made us board a different flight at 10:45. These people should not be running an airline--it is dangerous! And what a nightmare!

YUL
YTZ
Okay 5.6

once we took off it was fine

YTZ
IAD
Excellent 10.0

The convenience at YTZ airport.

The lack of personnel at the Porter counters at Dulles. Even though I had paid for luggage online and checked in I still had to wait in line for a very long time. There should be a separate line for pre check ins and no carry on.

Sat, 29 Sep
YVR
Vancouver Intl
MDW
Chicago Midway
6h 17m
Mon, 1 Oct
MDW
Chicago Midway
YVR
Vancouver Intl
7h 34m
C$ 429
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 18,980 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSY
SLC
Excellent 10.0

Great services ce.

LHR
SLC
Good 7.6

One of the older male flight attendants was not polite. Got a ride, short response when asking him for anything.

CUN
TPA
Excellent 8.6

Service is excellent. And the comfort too.

A couple of rude passengers that were complaining for everything and I felt Delta crew had to be a little more strict with that situation specially when other customers want to have a comfortable and pleasant flight .

SFO
JFK
Okay 4.3

Call center tried moving us to later flight that was also delayed by 3 hrs despite telling us it was on time. Fortunately a gate agent moved us back to orig flight

SLC
LAS
Good 6.0

The landing was somewhat frightening.

Sun, 21 Oct
YUL
Montreal Pierre Elliott Trudeau International
MDW
Chicago Midway
6h 42m
Wed, 24 Oct
MDW
Chicago Midway
YUL
Montreal Pierre Elliott Trudeau International
5h 10m
C$ 317
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1,982 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YUL
YTZ
Okay 5.6

once we took off it was fine

YTZ
BOS
Okay 4.6

After paying for bag check & being at the airport 3 hours early, the aIn-line was over weight so they removed my bag to the next flight, rather than the gate checked bags! They promised me the bags would be delivered right away, then after I checked, lied to me that they had been picked up by the delivery service.

YTZ
EWR
Excellent 9.3

Snacks and drink were provided, even on a short trip

I had a window seat, and the side protrudes towards the bottom amongst the inside, so I had less space on my window side

YTZ
IAD
Excellent 10.0

The convenience at YTZ airport.

The lack of personnel at the Porter counters at Dulles. Even though I had paid for luggage online and checked in I still had to wait in line for a very long time. There should be a separate line for pre check ins and no carry on.

EWR
YTZ
Excellent 8.0

Flight took off 30 min late

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