C$154 Cheap Flights from Montreal (YMQA) to Chicago (CHIA)

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Flight deals from Montreal to Chicago

Looking for a cheap last-minute deal or the best return flight from Montreal to Chicago? If you want to travel next month, return fares start from C$235. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Montreal to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Montreal to Chicago flights are currently cheapest in May.

Which airlines fly from Montreal to Chicago?

Montreal to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$154
Cheapest month to flyMay
Average flight time2 hrs, 43 mins
Most popular airlineAir Canada
Average flights per week277

Finding cheap flights from Montreal to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Montreal to Chicago is C$234. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 43 minutes is the average flight time from Montreal to Chicago.
Air Canada, United and Copa fly direct from Montreal to Chicago.
As of April 2026, there are 282 flights per week flying from Montreal to Chicago.
The cheapest month to fly from Montreal to Chicago is usually May.
If you're flying from Montreal, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from C$234.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Montreal to Chicago on Friday, May 22, 2026.
Yes – the average flight time is 2 hours and 43 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Porter Airlines. And the cheapest airline that flies to Chicago O'Hare International Airport is Air Canada.

Flying from Montreal to Chicago: what you need to know

  • Montreal's main base, Montreal-Pierre Elliott Trudeau International Airport (YUL), is where many unforgettable trips begin. Explore the options for leaving from here when booking your flight from Montreal to Chicago.

  • O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are Chicago's major gateways.

  • A direct flight from Montreal to Chicago takes on average 2 hours 39 minutes. The timezone in Chicago is UTC-5, which is 1 hour behind Montreal.

  • With 63 weekly flights between the two airports, Montreal-Pierre Elliott Trudeau International Airport (YUL) to O'Hare International Airport (ORD) is the busiest route. Board the first flight from Montreal to Chicago with United Airlines at 06:00. If you're keen to make the most of your day before leaving, the last departure from YUL to ORD is with Air Canada at 19:45.

  • To ensure you catch your flight from Montreal to Chicago, leave plenty of time to navigate the airport and find your gate. Arriving two hours before international departures and an hour before domestic flights is the standard rule.

  • If you're travelling during a major holiday or other peak period, allow extra time. A good general rule is two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

  • You don't need a visa for United States if you have a passport from Canada and are visiting for tourism purposes. Travel documentation and visa requirements can be subject to change. So before reserving your cheap flights from Montreal to Chicago, check with your airline and your destination country's local embassy or consulate for the latest rules.

Flying from Montreal

Montreal-Pierre Elliott Trudeau International Airport (YUL)

  • You can reserve a direct flight from Montreal to Chicago taking off from Montreal-Pierre Elliott Trudeau International Airport (YUL). Start your journey at YUL and touch down at O'Hare International Airport (ORD).

  • You'll have your choice of carriers offering direct flights from Montreal to Chicago departing from YUL. Get on board with any of these:

  • Located around 26 kilometres from the centre of Montreal, YUL can be reached in about 25 minutes by car, depending on traffic. The same journey on public transport will take roughly 2 hours and 15 minutes.

  • After an easy start to your journey? Stay near Montreal-Pierre Elliott Trudeau International Airport. Whether you've booked an early flight from Montreal to Chicago or want to avoid feeling rushed, these hotels are just the thing:

Arriving in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

How to find the cheapest flights from Montreal to Chicago

  • C$154 is the best price for a one-way ticket from Montreal to Chicago. Return flights start at C$234. These fares can change depending on demand.

  • To score cheap flights from Montreal to Chicago, reserve your trip 9 months before the departure date.

  • May is the cheapest month for tickets from Montreal to Chicago. If you're looking to travel during a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

  • Getting a cheap ticket from Montreal to Chicago couldn't be easier with Price Alerts. Simply set up one of these automatic alerts and we'll notify you as soon as there's a better deal.

  • Tailor your travel plans using filters. Choose your preferred departure and arrival times, airlines and total journey duration. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Montreal to Chicago.

Best time to go to Chicago

  • August is the most popular month for flights from Montreal to Chicago. To skip the crowds, visit Chicago in February.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your flights from Montreal to Chicago in this month if this is the type of weather you enjoy.

  • January sees average temperatures of between -12ºC and 3ºC. Search for cheap flights from Montreal to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

  • After booking your flight from Montreal to Chicago, think about where you'd like to stay in this city. Make one of these accommodation options your base for exploring Chicago:

  • Every great journey has to include a little sightseeing. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are must-visits when exploring Chicago.

Complete your Chicago trip with a car rental

  • We use the same magic that helped you find your cheap flight from Montreal to Chicago to track down deals on car rentals. Search for your ride in seconds and compare your options in one place. Plus we give you all the info you need to drive in Chicago, from the most popular car type to the best time to book.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.