Cheap Flights from Montreal Pierre Elliott Trudeau to Chicago Midway

Compare Montreal Pierre Elliott Trudeau 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 Pierre Elliott Trudeau to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Montreal Pierre Elliott Trudeau Airport to Chicago Midway Airport? If you want to travel next month, return fares start from R 2,788. Find the lowest prices on one-way and return tickets right here.

Chicago.R 1,816 per passenger.Departing Tue, 26 May.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Tue, 26 May, arriving in Chicago Midway.Price includes taxes and charges.From R 1,816, select.

Chicago.R 1,835 per passenger.Departing Mon, 1 Jun.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Mon, 1 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 1,835, select.

Chicago.R 2,509 per passenger.Departing Wed, 29 Jul.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Wed, 29 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 2,509, select.

Chicago.R 2,689 per passenger.Departing Thu, 6 Aug.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Thu, 6 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 2,689, select.

Chicago.R 2,939 per passenger.Departing Mon, 2 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From R 2,939, select.

Chicago.R 2,939 per passenger.Departing Sat, 10 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Sat, 10 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 2,939, select.

Chicago.R 2,941 per passenger.Departing Sun, 13 Sep.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Sun, 13 Sep, arriving in Chicago Midway.Price includes taxes and charges.From R 2,941, select.

Chicago.R 3,128 per passenger.Departing Wed, 29 Apr.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Montreal Pierre Elliott Trudeau on Wed, 29 Apr, arriving in Chicago Midway.Price includes taxes and charges.From R 3,128, select.

Chicago.R 3,829 per passenger.Departing Thu, 21 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Montreal Pierre Elliott Trudeau on Thu, 21 Jan, arriving in Chicago Midway.Price includes taxes and charges.From R 3,829, select.

Chicago.R 4,176 per passenger.Departing Sat, 26 Dec.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Montreal Pierre Elliott Trudeau on Sat, 26 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 4,176, select.

Find the cheapest month to fly from Montreal Pierre Elliott Trudeau to Chicago Midway

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

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Montreal Pierre Elliott Trudeau to Chicago Midway: Alternative routes

Compare routes from Montreal Pierre Elliott Trudeau 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	R 1,816
Cheapest month to fly	May

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

How much are return flights from Montreal Pierre Elliott Trudeau to Chicago Midway?

The best price we found for a return flight from Montreal Pierre Elliott Trudeau to Chicago Midway is R 2,778. 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 Pierre Elliott Trudeau to Chicago Midway?

Currently, there are no airlines that fly direct from Montreal Pierre Elliott Trudeau to Chicago Midway. But we found flights with one or more stops from R 2,778.

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

As of April 2026, there are no flights flying from Montreal Pierre Elliott Trudeau to Chicago Midway.

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

The cheapest month to fly from Montreal Pierre Elliott Trudeau to Chicago Midway is usually June.

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Montreal Pierre Elliott Trudeau Airport to Chicago Midway Airport on Thursday, 4 June 2026.

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

No airlines currently offer direct flights between Montreal Pierre Elliott Trudeau Airport 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 Pierre Elliott Trudeau Airport to Chicago Midway with?

Currently, Porter Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Montreal-Pierre Elliott Trudeau International Airport (YUL) to Chicago Midway International Airport (MDW): what you need to know

The timezone in Chicago is UTC-5, which is one hour behind Montreal.
Your YUL to MDW flight won't wait if you're late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.
Travelling during a peak time like August? School holidays and other popular seasons can lead to longer queues and delays at check-in and security. Play things extra safe and arrive up to four hours before international flights and two hours before domestic departures.

How to find the cheapest flights from Montreal-Pierre Elliott Trudeau International Airport (YUL) to Chicago Midway International Airport (MDW)

The lowest price we've found for a one-way Montreal-Pierre Elliott Trudeau International Airport to Chicago Midway International Airport flight is R 1,816. A return ticket is currently R 2,778. Depending on the availability when you book, these fares could change.
To find cheap tickets from YUL to MDW, book in advance. Airlines generally offer their most competitively priced fares when flights are first made available.
If you can be flexible with your travel plans, try using the 'Whole month' tool. It'll show you the cheapest price across each month when searching for a flight from Montreal-Pierre Elliott Trudeau International Airport to Chicago Midway International Airport.
You don't need to check every day to see if fares have dropped when you create a Price Alert. We'll notify you the moment the price changes on cheap flights from YUL to MDW.
Discover the ideal flight for you by using the filters. To see the 'Fastest,' 'Cheapest' or 'Best' flights from Montreal-Pierre Elliott Trudeau International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter by departure and arrival times, airline, and number of stops.

Handy information about Montreal-Pierre Elliott Trudeau International Airport (YUL)

You'll find YUL at 975 Romeo Vachon Street North.
Of the departures from Montreal-Pierre Elliott Trudeau International Airport, 64.89% land on time at their destination.
Central Montreal to Montreal-Pierre Elliott Trudeau International Airport is approximately 26 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're ride-sharing, catching a cab or driving.
Catching public transport? You can expect a journey time of around 2 hours 15 minutes.
Get your travels off to a hassle-free start by staying near YUL. Whether you're taking an early flight from Montreal-Pierre Elliott Trudeau International Airport to Chicago Midway International Airport or want to avoid feeling rushed, these hotels are perfect:

Arriving at Chicago Midway International Airport (MDW)

If you're getting in on a late Montreal-Pierre Elliott Trudeau International Airport to Chicago Midway International Airport flight, few things top the convenience of staying near the terminal. Grab your suitcases from the carousel and then be showered and snoozing not long after at one of these hotels near MDW:
Hit the road running by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and experience the lesser-explored corners of Chicago and beyond.
For the best deal, reserve your vehicle from Chicago Midway International Airport about four weeks before you travel.

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

MDW is located at 5700 South Cicero.
From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre by car.
When travelling by public transport, expect a journey of about 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

It's time to choose your dates for your flight from Montreal-Pierre Elliott Trudeau International Airport to Chicago Midway International Airport. July is the busiest month to head to Chicago. If you prefer a more low-key vibe, go in May.
The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your flights from Montreal-Pierre Elliott Trudeau International Airport to Chicago Midway International Airport in this month if this is the type of weather you like.
Search for cheap tickets from YUL to MDW in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of United States

Chicago has its own special appeal, but there are so many other parts of United States just waiting to be explored. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the go. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Indianapolis is another sought-after destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.