Cheap Flights from Montreal (YMQA) to Chicago Midway (MDW)

Compare Montreal to Chicago Midway flight deals

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

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Flight deals from Montreal to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Montreal to Chicago Midway Airport? If you want to travel next month, return fares start from £174. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Montreal to Chicago Midway

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

Montreal to Chicago: Flight information

The things to know before you go.
Cheapest flight found£105
Cheapest month to flyMay

Finding cheap flights from Montreal to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Montreal to Chicago Midway is £132. 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.
Currently, there are no airlines that fly direct from Montreal to Chicago Midway. But we found flights with one stop from £132.
As of March 2026, there are no flights flying from Montreal to Chicago Midway.
The cheapest month to fly from Montreal to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Montreal to Chicago Midway Airport on Friday, 8 May 2026.
No airlines currently offer direct flights between Montreal and Chicago Midway Airport. Most routes have one or more stops.
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 Midway 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.
The cheapest airline that flies to Chicago Midway is Porter Airlines .

Flying from Montreal to Chicago Midway International Airport (MDW): What you need to know

  • Chicago Midway International Airport is located in Chicago. The city operates on the UTC-6 timezone and is one hour behind Montreal.

  • Get to the airport on time so you don't miss your flight from Montreal to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the stress of rushing.

  • Show up at the airport even earlier during popular months like July. Aim for two hours before a domestic departure and up to four hours for an international flight. After checking in, you can use any extra time to relax or find something to eat.

Airports in Montreal

Montreal-Trudeau International Airport (YUL)

  • YUL is around 19 kms (12 miles) from central Montreal. If you're driving, catching a taxi or ride-sharing from the centre, it'll take 25 minutes or so to get there, depending on traffic. If you're taking public transport, expect the trip time to be around 45 minutes.

  • Planning to catch an early flight from Montreal to Chicago Midway International Airport? Avoid the mad dash to the terminal (and sneak in some extra snooze time) by staying at one of these stays near Montreal-Trudeau International Airport:

  • When it comes to the on-time performance of Montreal-Trudeau International Airport, 65% of flights meet their scheduled arrival time.

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

Montreal Metropolitan Airport (YHU)

About Chicago Midway International Airport (MDW)

  • The last thing you want is a long journey to your hotel if you're arriving on a late flight from Montreal to Chicago Midway International Airport. Stay at one of these accommodation options near MDW instead:

  • Follow your own route with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and venture far and wide through Chicago and beyond.

  • Get the best deal by reserving your vehicle around four weeks before your Montreal to Chicago Midway International Airport flight.

  • You'll find MDW at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • From Chicago Midway International Airport, central Chicago is around 16 kms (10 miles) away. It takes about 25 minutes to get to the city centre by car.

  • It takes around 30 minutes to get there using public transport.

How to find the cheapest flights from Montreal to Chicago Midway International Airport (MDW)

  • At the moment, £105 is the lowest price we've found for a one-way ticket from Montreal to Chicago Midway International Airport. The cheapest price for a return flight is £132. Keep in mind fares can change due to demand at the time of booking.

  • Don't leave things to the last minute. You're more likely to walk away with cheap flights from Montreal to MDW if you book in advance. Airlines often have some fantastic early bird rates.

  • The 'Whole month' tool shows you the cheapest Montreal to Chicago Midway International Airport tickets throughout the month. It's a good way to snap up a bargain if your plans aren't set in stone.

  • Spend less time searching for cheap plane tickets from Montreal to MDW by setting up a Price Alert. We'll send you an email or notification through the app when fares go down.

  • Save money on your flight from Montreal to Chicago Midway International Airport by using filters. Choose your ideal duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Montreal to Chicago Midway International Airport (MDW)

  • Think about your travel style when planning the timing of your trip. July is the quietest month to visit Chicago. March is when most people book flights from Montreal to Chicago Midway International Airport (MDW), which may be perfect if you're chasing more excitement.

  • Book a Montreal to MDW plane ticket departing in July if you're eager to visit the city during its warmest month. Expect temperatures in Chicago to range from 15ºC to 29ºC.

  • January has temperatures of between -12ºC and 3ºC. Look for cheap tickets from Montreal to Chicago Midway International Airport around that time if you like cooler conditions.

More about Chicago

Explore more of the United States

  • Chicago has plenty going for it, but there are so many other parts of the United States waiting to be explored. About 257 kms (160 miles) southeast of Chicago, a visit to Indianapolis will keep your itinerary busy. Start with popular sights like Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

  • If you're looking to explore another major destination in the United States, consider Milwaukee, roughly 137 kms (85 miles) north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are among its highlights.

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