Find Cheap Flights from Montreal to Chicago Midway (YMQ - MDW)

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FAQs for Booking Montreal to Chicago Midway Flights

How long does a flight from Montreal to Chicago Midway take?
An average nonstop flight takes 3h 35m, covering a distance of 1210 km.
Which airlines provide the cheapest flights from Montreal to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines (C$ 297)
Do I need a passport to fly between Montreal and Chicago Midway?
Yes.
What’s the cheapest day of the week to fly from Montreal to Chicago Midway?
For Montreal to Chicago Midway, Sunday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago Midway back to Montreal, the best deals are generally found on Tuesday, with Saturday 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$ 321 or less.

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

Airports
Origin
Montreal
C$ 297
only
C$ 297
Destination
Chicago
C$ 297
only
C$ 297
Sun, 21 Jan
YUL
MDW
5h 04m
Sat, 10 Feb
MDW
YUL
5h 45m
C$ 297
Trip: 21 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
IAD
Excellent 10.0

Smaller gate lounge area with lots of private space and complimentary drinks and snack. All Porter employees that I had interaction were professional and attentive to my needs

No suggestion

YUL
YTZ
Okay 5.6

The service was great and fast

Both of my Porter Airlines flights were delayed. It seems they often delay / cancel flights

YQG
YTZ
Excellent 8.0

Courteous, professional, friendly crew. Great service.

N/A

YTZ
EWR
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

YTZ
BOS
Excellent 10.0

Great service. Efficient.

Sat, 3 Mar
YUL
MDW
5h 50m
Tue, 6 Mar
MDW
YUL
5h 00m
C$ 299
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YOW
YTZ
Excellent 10.0

On time. Provided snacks and drinks even on a short flight. Group lobby prior to boarding provided coffee, tea, snacks, water for free.

YTZ
IAD
Excellent 10.0

Smaller gate lounge area with lots of private space and complimentary drinks and snack. All Porter employees that I had interaction were professional and attentive to my needs

No suggestion

YTZ
EWR
Okay 4.0

Delayed twice. No compensation for delays that resulted in hotel cancellations.

IAD
YTZ
Excellent 8.0

Fast check in and customs lines in both airports

The chips are pretty bland. I appreciate the free refreshments, but would like a bit of choice

YTZ
EWR
Excellent 10.0

as above

Sun, 25 Feb
YUL
MDW
4h 04m
Wed, 28 Feb
MDW
YUL
4h 50m
C$ 303
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YUL
YTZ
Okay 5.6

The service was great and fast

Both of my Porter Airlines flights were delayed. It seems they often delay / cancel flights

YTZ
BOS
Excellent 10.0

Great service. Efficient.

YTZ
EWR
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

MDW
YTZ
Excellent 10.0

The earlier flight departure times are really good, the traffic is not jammed yet on the 401 and GEW. Custom waiting times are basically non existing in comparison to Pearson. Planes are relatively on time (only flew 4 times with Porte), staff is friendly. The turboprop planes have more legroom than most others. I do like them, and do recommend Porter.

IAD
YTZ
Excellent 8.0

Fast check in and customs lines in both airports

The chips are pretty bland. I appreciate the free refreshments, but would like a bit of choice

Fri, 6 Apr
YUL
MDW
3h 35m
Sun, 8 Apr
MDW
YUL
3h 50m
C$ 308
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
YQB
Excellent 9.3

This was my first time flying Porter. The flight was a reasonable price, the service was great. The aircraft was a little on the smaller side but still spacious enough for comfortable travel.

IAD
YTZ
Excellent 8.0

Fast check in and customs lines in both airports

The chips are pretty bland. I appreciate the free refreshments, but would like a bit of choice

MDW
YTZ
Excellent 10.0

The earlier flight departure times are really good, the traffic is not jammed yet on the 401 and GEW. Custom waiting times are basically non existing in comparison to Pearson. Planes are relatively on time (only flew 4 times with Porte), staff is friendly. The turboprop planes have more legroom than most others. I do like them, and do recommend Porter.

YQG
YTZ
Excellent 8.0

Courteous, professional, friendly crew. Great service.

N/A

YTZ
IAD
Excellent 10.0

Smaller gate lounge area with lots of private space and complimentary drinks and snack. All Porter employees that I had interaction were professional and attentive to my needs

No suggestion

Thu, 8 Mar
YUL
MDW
4h 40m
Sun, 11 Mar
MDW
YUL
6h 00m
C$ 335
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YUL
YTZ
Okay 5.6

The service was great and fast

Both of my Porter Airlines flights were delayed. It seems they often delay / cancel flights

IAD
YTZ
Excellent 10.0

Porter Airline was amazing!! They use glasses instead of plastic cups! Nice, cheap, on time, and free wine!

YQG
YTZ
Excellent 8.0

Courteous, professional, friendly crew. Great service.

N/A

MDW
YTZ
Excellent 10.0

The earlier flight departure times are really good, the traffic is not jammed yet on the 401 and GEW. Custom waiting times are basically non existing in comparison to Pearson. Planes are relatively on time (only flew 4 times with Porte), staff is friendly. The turboprop planes have more legroom than most others. I do like them, and do recommend Porter.

YOW
YTZ
Excellent 10.0

On time. Provided snacks and drinks even on a short flight. Group lobby prior to boarding provided coffee, tea, snacks, water for free.

Thu, 28 Dec
YUL
MDW
6h 55m
Thu, 4 Jan
MDW
YUL
6h 05m
C$ 384
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
EWR
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

YTZ
BOS
Excellent 10.0

Great service. Efficient.

YTZ
EWR
Okay 4.0

Delayed twice. No compensation for delays that resulted in hotel cancellations.

IAD
YTZ
Excellent 8.0

Fast check in and customs lines in both airports

The chips are pretty bland. I appreciate the free refreshments, but would like a bit of choice

MDW
YTZ
Excellent 10.0

The earlier flight departure times are really good, the traffic is not jammed yet on the 401 and GEW. Custom waiting times are basically non existing in comparison to Pearson. Planes are relatively on time (only flew 4 times with Porte), staff is friendly. The turboprop planes have more legroom than most others. I do like them, and do recommend Porter.

Fri, 29 Dec
YUL
MDW
6h 55m
Thu, 4 Jan
MDW
YUL
6h 05m
C$ 384
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
YQB
Excellent 9.3

This was my first time flying Porter. The flight was a reasonable price, the service was great. The aircraft was a little on the smaller side but still spacious enough for comfortable travel.

YTZ
IAD
Excellent 10.0

Smaller gate lounge area with lots of private space and complimentary drinks and snack. All Porter employees that I had interaction were professional and attentive to my needs

No suggestion

YTZ
EWR
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

YOW
YTZ
Excellent 10.0

On time. Provided snacks and drinks even on a short flight. Group lobby prior to boarding provided coffee, tea, snacks, water for free.

YTZ
EWR
Excellent 10.0

as above

Wed, 3 Jan
YUL
MDW
5h 00m
Sat, 6 Jan
MDW
YUL
5h 00m
C$ 477
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 1728 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
EWR
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

YOW
YTZ
Excellent 10.0

On time. Provided snacks and drinks even on a short flight. Group lobby prior to boarding provided coffee, tea, snacks, water for free.

YTZ
IAD
Excellent 10.0

Smaller gate lounge area with lots of private space and complimentary drinks and snack. All Porter employees that I had interaction were professional and attentive to my needs

No suggestion

YTZ
EWR
Excellent 10.0

as above

YUL
YTZ
Okay 5.6

The service was great and fast

Both of my Porter Airlines flights were delayed. It seems they often delay / cancel flights

*
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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.