Find Cheap Flights from Montreal to Chicago (YMQ - CHI)

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Good to Know

Low Season:
January
Best time to beat the crowds
2%
expected price decrease
High Season:
May
Most popular time to fly
8%
expected price increase
Average Price:
$349
(avg. price over the last 2 weeks)
Good Deal:
$239
or less (round trip)

When to Book Flights from Montreal to Chicago

Average price per month
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 $239 or less.
The cheapest flight from Montreal to Chicago was found 37 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be April, May and June. The cheapest month to fly is January.
Morning departure is around 4% more expensive 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 Montreal to Chicago Flights

How long does a flight from Montreal to Chicago take?
An average nonstop flight takes 2h 30m, covering a distance of 744 miles.
How many flights are there between Montreal and Chicago?
There are 286 (nonstop) flights between Montreal and Chicago per week, averaging 41 per day.
Which airlines provide the cheapest flights from Montreal to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines ($231), Air Canada ($282) and Multiple Airlines ($282).
Do I need a passport to fly between Montreal and Chicago?
Yes.
Which airlines fly most frequently between Montreal and Chicago?
Air Canada (12 times daily), United (11 times daily), American Airlines (4 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Montreal to Chicago?
For Montreal to Chicago, Sunday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago back to Montreal, the best deals are generally found on Tuesday, with Monday being the most expensive.

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

Airports
Origin
Montreal
$231
only
$231
Destination
Chicago
$282
only
$282
$231
only
$231
Sun, Jan 21
YUL
MDW
5h 04m
Sat, Feb 10
MDW
YUL
5h 45m
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
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.

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
EWR
Excellent 10.0

as above

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

Mon, Jan 8
YUL
ORD
2h 30m
Sun, Jan 14
ORD
YUL
1h 58m
Trip: 7 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 100 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YUL
ORD
Excellent 10.0

Everything was perfect

YUL
ORD
Excellent 8.0

general state and size and comfort of the plane. Overall AC experience always good. The flight back to montreal, the service was exceptional!

only a dairy plate available, next time I need to specify no dairy entertainment -- too many ads and no previews for the movies so I have to start playing then stop and go through the entire same series of ads for the next one. the system just seems clunky and antiquated in today's tech age.

YUL
ORD
Excellent 8.0

On time, entertainment screen

that there is a charge for headphones

YUL
ORD
Good 7.0

Service flight on time food

No movies for 7 hour flight

YUL
ORD
Excellent 9.2

Professional fight attendants, very nice.

The flight took off late but most of the lost time was made up during the flight time.

Sun, Jan 21
YUL
ORD
2h 50m
Sat, Feb 10
ORD
YUL
2h 00m
Trip: 21 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Feb 9
YUL
ORD
6h 31m
Sun, Feb 11
ORD
YUL
7h 39m
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
JFK
YYZ
Excellent 10.0

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

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

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.

Thu, May 3
YUL
ORD
2h 38m
Sat, May 5
ORD
YUL
2h 16m
Trip: 3 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 3 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CLE
JFK
Mediocre 3.3

Plane was dirty and crew inattentive.

SFO
DFW
Excellent 10.0

On time. Comfortable seat. Courteous crew. Easy transfer.

JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

JFK
CDG
Mediocre 2.0

Nothing. From the plane to the awful delay and poor service.

Lack of communication. Old plane, no comfort and 6 HOURS DELAYED. Truly disappointed by the airline

YUL
MIA
Excellent 10.0

First time flyer with American airlines and the service was impeccable

Nothing to dislike

Sat, Mar 3
YUL
MDW
5h 50m
Tue, Mar 6
MDW
YUL
5h 00m
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
Okay 4.0

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

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

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.

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

YQG
YTZ
Excellent 8.0

Courteous, professional, friendly crew. Great service.

N/A

Wed, Jan 10
YUL
MDW
4h 45m
Fri, Jan 12
MDW
YUL
3h 40m
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
EWR
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

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.

YTZ
BOS
Excellent 10.0

Great service. Efficient.

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

Fri, Jan 19
YUL
ORD
2h 30m
Mon, Jan 22
ORD
YUL
2h 00m
Trip: 4 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 100 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YUL
ORD
Excellent 8.0

Seats were comfortable

35 minute delay in departing. Sat on plane at gate waiting to depart.

YUL
ORD
Okay 5.6

Fast loading and unloading.

Late!

YUL
ORD
Mediocre 3.6

Boarding was good, but pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!

Pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!

YUL
ORD
Good 6.0

$800 reimbursement 1st class

They overbooked the flight by 2 passengers.

YUL
ORD
Excellent 8.0

general state and size and comfort of the plane. Overall AC experience always good. The flight back to montreal, the service was exceptional!

only a dairy plate available, next time I need to specify no dairy entertainment -- too many ads and no previews for the movies so I have to start playing then stop and go through the entire same series of ads for the next one. the system just seems clunky and antiquated in today's tech age.

Fri, Feb 2
YUL
ORD
2h 50m
Wed, Feb 7
ORD
YUL
1h 58m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Feb 25
YUL
MDW
4h 04m
Wed, Feb 28
MDW
YUL
4h 50m
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
Okay 4.0

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

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.

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.

YTZ
EWR
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

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

Fri, Feb 16
YUL
ORD
7h 39m
Fri, Feb 23
ORD
YUL
7h 08m
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
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

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.

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.

Fri, May 4
YUL
ORD
2h 38m
Sun, May 6
ORD
YUL
2h 11m
Trip: 3 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 3 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

SFO
DFW
Excellent 10.0

On time. Comfortable seat. Courteous crew. Easy transfer.

JFK
CDG
Mediocre 2.0

Nothing. From the plane to the awful delay and poor service.

Lack of communication. Old plane, no comfort and 6 HOURS DELAYED. Truly disappointed by the airline

CLT
SJU
Mediocre 3.3

Direct flight

Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats

ATL
CLT
Excellent 9.6

The flight was late

Sun, Jan 21
YUL
ORD
2h 30m
Fri, Feb 9
ORD
YUL
2h 00m
Trip: 20 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 100 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YUL
ORD
Good 6.0

$800 reimbursement 1st class

They overbooked the flight by 2 passengers.

YUL
ORD
Excellent 9.2

Professional fight attendants, very nice.

The flight took off late but most of the lost time was made up during the flight time.

YUL
ORD
Excellent 10.0

Everything was perfect

YUL
ORD
Excellent 8.0

Seats were comfortable

35 minute delay in departing. Sat on plane at gate waiting to depart.

YUL
ORD
Good 7.0

Service flight on time food

No movies for 7 hour flight

Sat, Mar 3
YUL
ORD
2h 51m
Tue, Mar 6
ORD
YUL
2h 00m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 2
YUL
MDW
4h 25m
Wed, Mar 7
MDW
YUL
4h 50m
Trip: 6 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
IAD
YTZ
Excellent 10.0

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

YTZ
EWR
Excellent 10.0

as above

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

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
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

Thu, Mar 15
YUL
ORD
5h 47m
Mon, Mar 19
ORD
YUL
5h 22m
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

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

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.

Fri, Feb 2
YUL
ORD
2h 30m
Wed, Feb 7
ORD
YUL
2h 00m
Trip: 6 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 100 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YUL
ORD
Good 7.3

Comfortable seats, friendly crew.

Almost two hours delay each way.

YUL
ORD
Excellent 10.0

Everything was perfect

YUL
ORD
Excellent 8.0

Late flight No communication Had done pre register to sit with father. They changed his seat upon boarding.

YUL
ORD
Good 7.0

Service flight on time food

No movies for 7 hour flight

YUL
ORD
Excellent 8.0

On time, entertainment screen

that there is a charge for headphones

Thu, Mar 29
YUL
ORD
5h 47m
Fri, Apr 6
ORD
YUL
7h 12m
Trip: 9 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

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.

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, Jan 21
YUL
MDW
4h 04m
Fri, Feb 9
MDW
YUL
3h 40m
Trip: 20 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
BOS
Excellent 10.0

Great service. Efficient.

IAD
YTZ
Excellent 10.0

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

YTZ
EWR
Excellent 10.0

as above

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
Good 6.0

The flight attendants were very nice and helpful

The flight was delayed

Fri, Apr 20
YUL
ORD
2h 30m
Sun, Apr 22
ORD
YUL
2h 00m
Trip: 3 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 100 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YUL
ORD
Excellent 10.0

Everything was perfect

YUL
ORD
Good 6.0

$800 reimbursement 1st class

They overbooked the flight by 2 passengers.

YUL
ORD
Mediocre 3.6

Boarding was good, but pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!

Pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!

YUL
ORD
Okay 5.6

Fast loading and unloading.

Late!

YUL
ORD
Excellent 8.0

On time, entertainment screen

that there is a charge for headphones

Show more results
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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.