C$379 Cheap Flights from Montreal (YMQA) to Chicago Midway (MDW)

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Flight deals from Montreal to Chicago Midway

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 C$379. Find the lowest prices on one-way and return tickets right here.

Chicago.C$229 per passenger.Departing Sat., Sep. 12.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Sat., Sep. 12, arriving in Chicago Midway.Price includes taxes and charges.From C$229, select.

Chicago.C$232 per passenger.Departing Tue., Oct. 6.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Tue., Oct. 6, arriving in Chicago Midway.Price includes taxes and charges.From C$232, select.

Chicago.C$249 per passenger.Departing Tue., Feb. 16.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Tue., Feb. 16, arriving in Chicago Midway.Price includes taxes and charges.From C$249, select.

Chicago.C$250 per passenger.Departing Wed., Jan. 20.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Wed., Jan. 20, arriving in Chicago Midway.Price includes taxes and charges.From C$250, select.

Chicago.C$255 per passenger.Departing Wed., Jun. 30.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Wed., Jun. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$255, select.

Chicago.C$268 per passenger.Departing Sat., May 29.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Sat., May 29, arriving in Chicago Midway.Price includes taxes and charges.From C$268, select.

Chicago.C$268 per passenger.Departing Tue., Dec. 8.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Tue., Dec. 8, arriving in Chicago Midway.Price includes taxes and charges.From C$268, select.

Chicago.C$268 per passenger.Departing Wed., Nov. 11.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Wed., Nov. 11, arriving in Chicago Midway.Price includes taxes and charges.From C$268, select.

Chicago.C$298 per passenger.Departing Fri., Apr. 30.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Fri., Apr. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$298, select.

Chicago.C$302 per passenger.Departing Sun., Mar. 28.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Sun., Mar. 28, arriving in Chicago Midway.Price includes taxes and charges.From C$302, select.

Chicago.C$376 per passenger.Departing Mon., Aug. 31.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Mon., Aug. 31, arriving in Chicago Midway.Price includes taxes and charges.From C$376, select.

Chicago.C$635 per passenger.Departing Mon., Jul. 19.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal St Hubert on Mon., Jul. 19, arriving in Chicago Midway.Price includes taxes and charges.From C$635, select.

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 September.

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Montreal to Chicago Midway: Alternative routes

Compare routes from Montreal to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Montreal to Chicago: Flight information

The things to know before you go.

Cheapest flight found	C$229
Cheapest month to fly	September

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

How much are return flights from Montreal to Chicago Midway?

The best price we found for a return flight from Montreal to Chicago Midway is C$379. 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.

Which airlines fly direct from Montreal to Chicago Midway?

Currently, there are no airlines that fly direct from Montreal to Chicago Midway. But we found flights with one stop from C$379.

How many flights are there a week from Montreal to Chicago Midway?

As of August 2026, there are no flights flying from Montreal to Chicago Midway.

When is the cheapest time to fly from Montreal to Chicago Midway?

The cheapest month to fly from Montreal to Chicago Midway is usually September.

Which upcoming date is cheapest to fly from Montreal to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Montreal to Chicago Midway Airport on Wednesday, September 16, 2026.

Can I get a direct flight from Montreal to Chicago Midway Airport?

No airlines currently offer direct flights between Montreal and Chicago Midway Airport. Most routes have one or more stops.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Montreal to Chicago Midway with?

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

Planning your trip begins with working out where you'll fly out of in Montreal. Montreal-Pierre Elliott Trudeau International Airport (YUL) is the city's main base, so explore your options for reserving a flight from Montreal to Chicago Midway International Airport (MDW) jetting off from here.
Chicago is 1 hour behind Montreal. Chicago Midway International Airport is located in Chicago, which operates on the UTC-5 timezone.
Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Make sure you're at the airport on time to catch your flight from Montreal to MDW.
During popular months such as August, you'll want to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead of an international flight whenever you're flying during peak periods in general.

Airports in Montreal

Montreal-Pierre Elliott Trudeau International Airport (YUL)

From central Montreal, YUL is around 26 kilometres away. Use navigation apps or visit the official airport website to find the best way to arrive at the terminal.
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 Midway International Airport or just don't want to be rushed, these hotels are the answer:

About Chicago Midway International Airport (MDW)

If you're arriving on a late flight from Montreal to Chicago Midway International Airport, nothing tops the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and sleeping soon after at one of these options near MDW:

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

From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 21 minutes to get to the centre driving.
Travelling by public transport takes roughly 46 minutes.

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

The lowest price we've found for a one-way ticket from Montreal to Chicago Midway International Airport is C$229. The cheapest price for a return flight is C$379. Remember fares can change due to availability at the time of booking.
We suggest booking as soon as possible to lock in flight tickets from Montreal to MDW. You're more likely to score a great deal and have a wider selection of departure times and dates.
Getting flight tickets from Montreal to Chicago Midway International Airport is easier if you can be flexible with your travel plans. Use the 'Whole month' function to see the lowest prices across each month and land a great deal.
Locking in a cheap ticket from Montreal to MDW is a breeze with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know when the price drops.
Play around with the filters to find your ideal journey. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Montreal to Chicago Midway International Airport, use the 'Sort by' function. You can also filter by departure and arrival times, airline, and number of stops.

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

May is the quietest time to travel to Chicago. Alternatively, follow the crowds and go in July. This is the busiest month for flights from Montreal to Chicago Midway International Airport, but the best time to go is your call.
The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your flights from Montreal to MDW 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 Midway International Airport sometime then if you like cooler conditions.

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the best stays in Chicago right here. Check out these hotels as soon as you've booked your flight from Montreal to Chicago Midway International Airport:
There are so many things to do and see in this city it can be tricky to work out where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are popular attractions which should be on any good Chicago itinerary.

Complete your Chicago trip with a car rental

Close all those tabs and leave the hard work to us. We've also got awesome deals on car rentals in Chicago once you've booked your cheap flight from Montreal to Chicago Midway International Airport. Instantly compare prices in one place and drive off with the perfect rental for less.