Cheap flights from Montreal to Chicago

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The best prices from Montreal to Chicago are usually found in November or March, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

How to find the cheapest flight from
Montreal (YMQ) to Chicago (CHI)

YMQ - CHI
Price
C$ 367 - C$ 470
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

Popular in

August

High demand for flights, 12% potential price rise

Cheapest in

November

Best time to find cheap flights, 11% potential price drop

Round-trip from

C$ 367

From Montreal to Chicago

One-way from

C$ 269

One-way flight from Montreal to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Montreal to Chicago?

Tuesday is generally a great day to depart. Flying on this day could help you save up to 11%.

How far in advance should I book a flight from Montreal to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 61 days in advance, which can save you up to 81% on flights from Montreal to Chicago compared to booking the week you need them. Waiting 61 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 437. For sooner than that we have options available in the next 3 days from C$ 584.

What is the cheapest month to fly from Montreal to Chicago?

Flights from Montreal to Chicago lean towards being more expensive in August. Prices are generally better when you fly from Montreal to Chicago in February, with the cheapest ticket starting at C$ 240.

When is the cheapest time to fly from Montreal to Chicago (YMQ - CHI)?

Unlike in the evening, when flights are generally more expensive, you can save up to 21% on flights from Montreal to Chicago by exploring options for tickets in the afternoon.

Cheap flights from Montreal to Chicago in October, November 2020

The best prices found for YMQ to CHI flights for October, November
30 Nov - 15 Dec
C$ 373pp
YUL
Montreal Pierre Elliott Trudeau Intl
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
YUL
Montreal Pierre Elliott Trudeau Intl
30 Nov - 15 Dec
C$ 409pp
YUL
Montreal Pierre Elliott Trudeau Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
   
2 STOPS
YUL
Montreal Pierre Elliott Trudeau Intl
24 Nov - 1 Dec
C$ 419pp
YUL
Montreal Pierre Elliott Trudeau Intl
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
YUL
Montreal Pierre Elliott Trudeau Intl

Montreal to Chicago 2020 flight deals

Cheap flights to Chicago from Montreal found for this year
30 Nov - 15 Dec
C$ 373pp
YUL
Montreal Pierre Elliott Trudeau Intl
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
YUL
Montreal Pierre Elliott Trudeau Intl
4 Dec - 8 Dec
C$ 394pp
YUL
Montreal Pierre Elliott Trudeau Intl
Multiple Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YUL
Montreal Pierre Elliott Trudeau Intl
4 Dec - 8 Dec
C$ 398pp
YUL
Montreal Pierre Elliott Trudeau Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Iberia
 
1 STOP
YUL
Montreal Pierre Elliott Trudeau Intl

Direct flights to Chicago from Montreal

Save time with Montreal to Chicago direct flight deals
4 Dec - 8 Dec
C$ 399pp
YUL
Montreal Pierre Elliott Trudeau Intl
Multiple Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qantas Airways
Direct
YUL
Montreal Pierre Elliott Trudeau Intl
24 Dec - 3 Jan
C$ 461pp
YUL
Montreal Pierre Elliott Trudeau Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YUL
Montreal Pierre Elliott Trudeau Intl
24 Nov - 1 Dec
C$ 462pp
YUL
Montreal Pierre Elliott Trudeau Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YUL
Montreal Pierre Elliott Trudeau Intl

Last minute flights from Montreal to Chicago

Late deals on round-trip flights to Chicago from Montreal, departing today and this week
31 Oct - 2 Nov
C$ 652pp
YUL
Montreal Pierre Elliott Trudeau Intl
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YUL
Montreal Pierre Elliott Trudeau Intl
31 Oct - 2 Nov
C$ 833pp
YUL
Montreal Pierre Elliott Trudeau Intl
United Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
YUL
Montreal Pierre Elliott Trudeau Intl
31 Oct - 2 Nov
C$ 849pp
YUL
Montreal Pierre Elliott Trudeau Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
YUL
Montreal Pierre Elliott Trudeau Intl

One-way flights to Chicago from Montreal

The cheapest one-way flights from Montreal to Chicago
6:54 a.m. - 2:33 a.m.
American Airlines
2 stops
20h 39m
YUL - ORD
American Airlines
C$ 270
3:35 a.m. - 5:12 a.m.
United Airlines
Direct
2h 37m
YUL - ORD
United Airlines
C$ 431
KAYAK
2:25 p.m. - 6:44 a.m.
Multiple Airlines
3 stops
41h 19m
YUL - ORD
Multiple Airlines
C$ 3,784
Kiwi.com

Related info for your journey

Useful info, stats and facts about Montreal to Chicago flights.

Flight FAQs

From Montreal to Chicago

Can I find flights from Montreal to Chicago for under C$ 394 on Cheapflights?

Yes, there are multiple flights from Montreal to Chicago for under C$ 394. The cheapest flight booked recently is on American Airlines for just C$ 373, but on average you can expect to pay C$ 425.

What safety measures are being taken by airlines flying from Montreal to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travellers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Montreal to Chicago. Policies will vary by airline.

Which airlines flying from Montreal to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Montreal to Chicago have new flexible policies in place due to COVID-19. Air Canada, Porter Airlines, and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Air Canada with this kind of flexibility.

Are there direct flights from Montreal to Chicago for under C$ 525 on Cheapflights?

Cheapflights has 5 direct flights from Montreal to Chicago under C$ 525. A good price for a direct flight from Montreal to Chicago is less than C$ 483.

Are there last-minute flights available from Montreal to Chicago for under C$ 656?

There are currently 3+ open flights from Montreal to Chicago within the next 7 days for less than C$ 656.

Is Montreal weather warmer or cooler than Chicago?

Our data indicates that the weather will be 29 °C on average in the month of July. The temperature in Chicago is typically hotter than in Montreal. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.

How long is the flight from Montreal to Chicago?

A quick flight from Montreal to Chicago can take about 2h 35m. American Airlines provides one of the quickest options available for as low as C$ 460. All flights are typically direct.

What are the cheapest airlines to flying from Montreal to Chicago round-trip?

Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at C$ 373. Additional round-trip tickets that might be worth considering are offered by United Airlines and Porter Airlines, with the lowest prices starting at C$ 410 and C$ 431, respectively. You may be able to fly from Montreal to Chicago for 9% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Montreal to Chicago one-way?

One-way options have recently been found by users for as low as C$ 234 on American Airlines. Another option is United Airlines, who have fights from C$ 259.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Montreal to Chicago
Today's exchange rate
C$ 1 = $0.77
Flight duration
2h 31m
Average temperature for October in Chicago
18.0 °C
Avg rainfall for October in Chicago
66.0 mm

Airports servicing Montreal

Saint-Hubert Airport (YHU)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Montreal to Chicago

Morning 6 AM to noon 100% of YMQ to US-CHI departures
Early morning Midnight to 6 AM 0% of YMQ to US-CHI departures
Afternoon Noon to 6 PM 0% of YMQ to US-CHI departures
Evening 6 PM to midnight 0% of YMQ to US-CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Montreal to Chicago
Sunday
0 flights
Monday
2 daily flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
2 daily flights
Friday
0 flights
Saturday
0 flights
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