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Cheap flights from Montreal to Chicago

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Compare Montreal to Chicago flight deals

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Flight deals from Montreal to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Montreal to Chicago? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$245 per passenger.Departing Tue, Jun 17, returning Tue, Jul 1.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound indirect flight with Porter Airlines (Canada) Ltd, departing from Montreal Pierre Elliott Trudeau on Tue, Jun 17, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines (Canada) Ltd, departing from Chicago Midway on Tue, Jul 1, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$245, select.
Chicago.C$245 per passenger.Departing Tue, Jun 3, returning Tue, Jun 17.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound indirect flight with Porter Airlines (Canada) Ltd, departing from Montreal Pierre Elliott Trudeau on Tue, Jun 3, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines (Canada) Ltd, departing from Chicago Midway on Tue, Jun 17, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$245, select.
Chicago.C$245 per passenger.Departing Tue, May 20, returning Tue, Jun 3.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound indirect flight with Porter Airlines (Canada) Ltd, departing from Montreal Pierre Elliott Trudeau on Tue, May 20, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines (Canada) Ltd, departing from Chicago Midway on Tue, Jun 3, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$245, select.
Chicago.C$250 per passenger.Departing Sun, May 18, returning Sun, May 25.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound indirect flight with Porter Airlines (Canada) Ltd, departing from Montreal Pierre Elliott Trudeau on Sun, May 18, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines (Canada) Ltd, departing from Chicago Midway on Sun, May 25, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$250, select.
Chicago.C$252 per passenger.Departing Mon, Jul 7, returning Sun, Jul 13.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound indirect flight with Porter Airlines (Canada) Ltd, departing from Montreal Pierre Elliott Trudeau on Mon, Jul 7, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines (Canada) Ltd, departing from Chicago Midway on Sun, Jul 13, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$252, select.
Chicago.C$280 per passenger.Departing Thu, Jul 24, returning Mon, Jul 28.Round-trip flight with Air Canada.Outbound direct flight with Air Canada departing from Montreal Pierre Elliott Trudeau on Thu, Jul 24, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departing from Chicago O'Hare International on Mon, Jul 28, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$280, select.
Chicago.C$281 per passenger.Departing Sat, Jun 28, returning Wed, Jul 16.Round-trip flight with Air Canada.Outbound direct flight with Air Canada departing from Montreal Pierre Elliott Trudeau on Sat, Jun 28, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departing from Chicago O'Hare International on Wed, Jul 16, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$281, select.
Chicago.C$283 per passenger.Departing Wed, May 21, returning Wed, May 28.Round-trip flight with Air Canada.Outbound direct flight with Air Canada departing from Montreal Pierre Elliott Trudeau on Wed, May 21, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departing from Chicago O'Hare International on Wed, May 28, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$283, select.

When is the cheapest time 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 June.
Apr
from C$590
May
from C$250
Jun
from C$245
Jul
from C$252
Aug
from C$364
Sep
from C$332
Oct
from C$333
Nov
from C$363
Dec
from C$363
Jan
from C$371
Feb
from C$398
Mar
from C$399

Direct flights from Montreal to Chicago

Alternative Montreal to Chicago routes

Looking for the cheapest, fastest or easiest route from Montreal to Chicago? You could fly into the following airports instead.

Montreal to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$245
Cheapest month to flyMay
Average flight time2 hrs, 40 mins
Most popular airlineAir Canada
Average flights per week232

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 round-trip flight from Montreal to Chicago is C$245. 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 40 minutes is the average flight time from Montreal to Chicago.
Air Canada, United and Alaska Airlines fly direct from Montreal to Chicago.
There are 928 flights per week flying from Montreal to Chicago, as of April 2025.
The cheapest month to fly from Montreal to Chicago is usually April 2025.
If you're flying from Montreal, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the center of Chicago. We've found flights to this airport from C$245.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Montreal to Chicago on Tuesday, May 20, 2025.
Yes – the average flight time is 2 hours and 40 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 (Canada) Ltd, 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 countless awesome vacations begin. Explore the departure options from here when searching for a flight from Montreal to Chicago.

  • When it comes to choosing where to land in Chicago, O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the primary gateways.

  • The average length of a direct Montreal to Chicago flight is 2 hours 40 minutes.

  • Chicago's timezone is UTC-5, making Chicago one hour behind Montreal.

  • The busiest route for flights from Montreal to Chicago is from Montreal-Pierre Elliott Trudeau International Airport (YUL) to O'Hare International Airport (ORD). There are 46 weekly services between these two airports. If you want to get going as soon as possible, the earliest flight from YUL to ORD is the 06:00 United Airlines service. If you prefer to leave later in the day, the final scheduled service is at 19:45 with Air Canada.

  • Give yourself enough time to make your Montreal to Chicago flight. Generally, it's best to arrive two hours before international departures and an hour ahead for domestic flights.

  • Flying during a peak month like August? Public holidays and other popular seasons can lead to longer queues at check-in and security. Play things extra safe and arrive up to four hours ahead of an international flight and two hours before a domestic departure.

How to find the cheapest flights from Montreal to Chicago

  • Right now, C$159 is the best price we've found for a one-way ticket from Montreal to Chicago. The cheapest price for a return flight is C$245. Remember fares may change due to demand at the time of booking.

  • Lock in cheap Montreal to Chicago flights by booking two months ahead. Based on our research, that's the sweet spot for picking up a bargain.

  • The best month for picking up cheap plane tickets from Montreal to Chicago is May. Use the 'Whole month' tool to compare flight prices, then choose the dates with the lowest fares.

  • Locking in a cheap flight from Montreal to Chicago is easy with Price Alerts. All you need to do is create one of these automatic alerts and we'll notify you when there's a better deal.

  • Select your ideal departure and arrival times, number of stops and airlines by using the filters. Or sort your Montreal to Chicago flight results by 'Fastest,' 'Cheapest' or 'Best.'

Flying from Montreal

Montreal-Pierre Elliott Trudeau International Airport (YUL)

  • If you're searching for a direct flight from Montreal to Chicago, you can leave from Montreal-Pierre Elliott Trudeau International Airport (YUL). Get from YUL to O'Hare International Airport (ORD) in one seamless journey.

  • You can choose from various airlines offering direct Montreal to Chicago plane tickets with departures from YUL, including:

  • YUL is around 16 kilometres from central Montreal. If you're ride-sharing, catching a cab or driving from the centre, it'll take 25 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the journey time to be around 45 minutes.

  • Want an easy start to your break? Stay near Montreal-Pierre Elliott Trudeau International Airport. Whether you're taking an early flight from Montreal to Chicago or just don't like being rushed, these hotels are just the thing:

  • When it comes to Montreal-Pierre Elliott Trudeau International Airport's on-time performance, 64.89% of flights arrive within the scheduled time frame.

  • You'll find YUL at 975 Romeo Vachon Street North.

Arriving in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is approximately 26 kilometres. It takes around 35 minutes to reach the centre driving.

  • If you're travelling by public transport, expect a journey time of about 55 minutes.

  • If you have a late flight from Montreal to Chicago, nothing beats the convenience of staying near the terminal. Grab your suitcases from the carousel and then be showered and resting soon after at one of these hotels near ORD:

  • Travel at your own speed with an O'Hare International Airport rental car. Book your wheels from Routes Car Rentals, Dollar or Budget and discover more of Chicago and beyond.

  • To lock in the lowest price, book your vehicle from O'Hare International Airport around four weeks ahead of your Montreal to Chicago flight.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is roughly 14 kilometres from the centre of Chicago. After your flight from Montreal to Chicago, it'll take you approximately 20 minutes to reach the heart of the city in a cab or ride-share.

  • You can expect the journey to take approximately 45 minutes on public transport.

  • You'll find some comfortable places ready to welcome you near MDW. Unwind after your Montreal to Chicago flight at one of these perfectly located options:

  • Forget about public transport schedules or slow-moving cab lines. Pick up a Chicago Midway International Airport rental car and let the journey unfold your way. Check out the availability and rates from Dollar, Hertz and Budget.

  • Get what you want, not just what's left over. Reserving your ride from MDW four weeks ahead of time often means lower prices and a greater range of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 129 kilometres from central Chicago. It'll take you about 1 hour 25 minutes to get to the city centre in a car once you've hopped off your flight from Montreal to Chicago.

  • The journey takes about 4 hours 15 minutes by public transport.

  • Take control of the next leg of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are dependable companies for booking.

  • If you're looking for a certain make or model, booking early gives you a better shot at getting your first choice. Reserve your ride from RFD at least a couple of weeks ahead of your flight from Montreal to Chicago.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

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 January.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Montreal to Chicago ticket then if that's your definition of good weather.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap flights from Montreal to Chicago around that time if you want to travel when it's cooler.

More about Chicago

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another standout destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Montreal to Chicago

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