Cheap Flights from Montreal (YUL) to Chicago (PWK)

Popular airlines from Montreal–Trudeau Intl. Airport (YUL) to Chicago, IL (PWK-Chicago Executive)

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Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $416
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $416
Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $337
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $337

Frequently asked questions

How much does a flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK) cost?
Grab a cheap one-way flight or cheap return flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK)?
Planning your trip for may help you find better deals, as it's the cheapest month for flights between YUL and PWK. You'll typically find the lowest fares during off-peak months.
How many flights per day from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK)?
Direct flights from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from YUL to PWK?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK)?
To reach Chicago Executive Airport (PWK) on schedule, opt for a flight that takes off from Pierre Elliott Trudeau Intl. Airport (YUL) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Pierre Elliott Trudeau Intl. Airport (YUL)?
Browse your flight options from Pierre Elliott Trudeau Intl. Airport (YUL) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can fly into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK) last-minute?
Holding off until just before your trip to book a flight from YUL to PWK often results in higher prices. While you might find some last-minute discounts, there's no guarantee. Keep your travel plans flexible for a better chance of scoring a bargain.
Is it cheaper to book a YUL to PWK flight and hotel package?
Compared with arranging hotels and flights separately, booking a YUL to PWK flight and hotel package with Expedia could lead to significant savings. What's more, managing everything in one place will take the stress out of planning your trip. Just secure your flights and choose from our extensive range of stays, then customize your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Executive Airport (PWK)?
In most instances, you're able to reschedule or cancel your YUL to PWK flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you'd like more information, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
Chicago Executive
Distance
741 mi

Book with confidence

Book with confidence

Montreal to Chicago Flights

The cheapest times to fly from Montreal to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Montreal to Chicago are during the month of . You can find some of the cheapest flights from Montreal to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Montreal to Chicago

Sunday is one of the best days to book for cheap flights from Montreal to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Montreal to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Montreal to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Montreal to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Montreal to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Montreal to Chicago Flights

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*Available to One Key members.