Cheap flights from Montreal (YMQA) to Chicago (CHIA)

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      Compare Montreal to Chicago flight deals

      Find the cheapest month or even day of the year to fly to Chicago

      Book the best Chicago fare with no extra fees

      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 $307. 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 October.

      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 found$182
      Cheapest month to flyOctober
      Average flight time2 hrs, 42 mins
      Most popular airlineAir Canada
      Average flights per week234

      Finding cheap flights from Montreal to Chicago: Frequently asked questions

      There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
      The best price we found for a return flight from Montreal to Chicago is $307. 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 42 minutes is the average flight time from Montreal to Chicago.
      Air Canada, United and Alaska Airlines fly direct from Montreal to Chicago.
      As of July 2026, there are 234 flights per week flying from Montreal to Chicago.
      The cheapest month to fly from Montreal to Chicago is usually August.
      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 $307.
      After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Montreal to Chicago on Wednesday, 5 August 2026.
      Yes – the average flight time is 2 hours and 42 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 July, the average temperature is usually around 22°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.

      Travelling from Montreal to Chicago: what you need to know

      • Montreal's main base, Montreal Pierre Elliott Trudeau Airport (YUL), is where countless awesome holidays begin. Explore the departure options from here when planning your flight from Montreal to Chicago.

      • Step off your plane in Chicago at Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW).

      • Hop on a direct Montreal to Chicago flight and you'll be travelling for an average of 2 hours 40 minutes.

      • The timezone in Chicago is UTC-6, which is one hour behind Montreal.

      • Montreal Pierre Elliott Trudeau Airport (YUL) to Chicago O'Hare International Airport (ORD) is the most traveled route between these two cities. There are 49 flights a week to pick from. If you prefer a later start to the day, the last flight from Montreal to Chicago is with Air Canada at 18:50. Opt for the first YUL to ORD departure with United Airlines at 06:00 to fit in more activities on your first day in Chicago.

      • To ensure you make your Montreal to Chicago flight, leave plenty of time to check in and drop off your luggage. Arriving two hours before international departures and one hour before domestic flights is the standard rule.

      • Be prepared for bigger queues in popular months such as July. Arriving up to four hours in advance for an international flight and two hours for domestic departures is a smart move.

      How to find the cheapest flights from Montreal to Chicago

      • Don't wait until the last minute. You're more likely to find cheap Montreal to Chicago flights if you book early. Airlines often offer some amazing early bird discounts.

      • If you're willing to be flexible with your trip dates, try using the 'Whole month' search tool. It'll show you the lowest price across the month when looking for your plane ticket from Montreal to Chicago.

      • There's no need to search every day to see if fares have dropped when you create a Price Alert. We'll let you know when a better deal comes up on cheap flights from Montreal to Chicago.

      • Find a cheap Montreal to Chicago flight with the help of our filters. Select your preferred times, airlines and number of stops, then sort the results by 'Cheapest' to see the best deals.

      Flying from Montreal

      Montreal Pierre Elliott Trudeau Airport (YUL)

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

      • Well-known carriers that offer direct Montreal to Chicago plane tickets departing from YUL include:

      • The journey from central Montreal to YUL takes about 45 minutes on public transport. If you ride-share, drive or grab a taxi, you'll cover the 16 kilometres in 25 minutes or so, depending on traffic.

      • Catching an early flight from Montreal to Chicago? Avoid the stress of rushing to the airport (and sneak in some extra snooze time) by choosing one of these hotels near Montreal Pierre Elliott Trudeau Airport:

      • When it comes to Montreal Pierre Elliott Trudeau Airport's on-time performance, data shows 67% of flights arrive within the scheduled time frame.

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

      Arriving in Chicago

      Chicago O'Hare International Airport (ORD)

      • Chicago O'Hare International Airport (ORD) to central Chicago takes about 30 minutes to reach by car. The centre is roughly 26 kilometres away.

      • It typically takes 45 minutes to get there when travelling by public transport.

      • If you're arriving on a late flight from Montreal to Chicago, few things beat the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and snoozing soon after at one of these accommodation options near ORD:

      • Pick up a Chicago O'Hare International Airport rental car and discover Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are leading providers you can book with here.

      • Lock in the lowest price by reserving your ride from Chicago O'Hare International Airport about four weeks before your departure date.

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

      Chicago Midway Airport (MDW)

      • After your flight from Montreal to Chicago has hit the runway, you can reach the city centre in around 25 minutes by car. Central Chicago is roughly 14 kilometres from Chicago Midway Airport (MDW).

      • If you hop on public transport, you'll get to the city centre in 30 minutes or so.

      • After your flight from Montreal to Chicago, unwind at a hotel near MDW. These are some comfortable accommodation options that'll help you slip into relaxation mode:

      • Dollar, Hertz and Budget make collecting a Chicago Midway Airport rental car quick and easy. These trusted providers are located around or in the terminal and will have you behind the wheel before you know it.

      • Snap up the best price by booking your ride from MDW four weeks in advance. You can also expect to have a bigger selection of vehicles.

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

      Chicago Rockford Airport (RFD)

      • Hop off your flight from Montreal to Chicago and head directly to your hotel or start taking in the sights right away. Central Chicago is around 129 kilometres from Chicago Rockford Airport (RFD) and usually takes 1 hour 40 minutes to drive there.

      • Public transport can take you there in roughly 2 hours.

      • Put yourself in the driver's seat of the next leg of your journey by picking up a Chicago Rockford Airport rental car. Budget, Alamo and National are some companies you can book with.

      • Rental companies sometimes offer discounts on early bookings, so reserve your vehicle from RFD a few weeks in advance of your flight from Montreal to Chicago. A little planning can save you money.

      • Chicago Rockford Airport's address is 2 Airport Cir.

      Best time to go to Chicago

      • March is the quietest month for flights from Montreal to Chicago, while July is the most popular. Figure out the best time to visit Chicago based on whether you prefer a lively atmosphere or a more laid-back vibe.

      • Lock in a Montreal to Chicago ticket departing in July if you want to visit the city during its warmest month. Expect temperatures in Chicago to range from 16ºC (61ºF) to 28ºC (82ºF).

      • If you want to travel in cooler conditions, look for a cheap flight from Montreal to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

      More about Chicago

      Explore more of the United States

      • Columbus is just one of the many places in the United States waiting to be discovered after you've experienced Chicago. Around 451 kilometres to the southeast, top sights here include Franklin Park Conservatory and Botanical Gardens, Columbus Park of Roses and Ohio Theatre.

      • Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. Experience major highlights starting with Lucas Oil Stadium, Eiteljorg Museum of American Indians and Western Art and The Children's Museum of Indianapolis.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.