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Cheap flights from Montreal to Chicago Midway

Compare Montreal to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Montreal to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Montreal to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$276 per passenger.Departing Thu, Sep 4, returning Mon, Sep 8.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Montreal Pierre Elliott Trudeau on Thu, Sep 4, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departing from Chicago Midway on Mon, Sep 8, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$276, select.
Chicago.C$298 per passenger.Departing Fri, Oct 24, returning Tue, Oct 28.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Montreal Pierre Elliott Trudeau on Fri, Oct 24, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Tue, Oct 28, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$298, select.
Chicago.C$327 per passenger.Departing Thu, Aug 28, returning Sun, Aug 31.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Montreal Pierre Elliott Trudeau on Thu, Aug 28, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departing from Chicago Midway on Sun, Aug 31, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$327, select.
Chicago.C$331 per passenger.Departing Wed, Sep 24, returning Wed, Oct 1.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Montreal Pierre Elliott Trudeau on Wed, Sep 24, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departing from Chicago Midway on Wed, Oct 1, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$331, select.
Chicago.C$333 per passenger.Departing Fri, Aug 29, returning Fri, Sep 5.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Montreal Pierre Elliott Trudeau on Fri, Aug 29, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departing from Chicago Midway on Fri, Sep 5, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$333, select.
Chicago.C$366 per passenger.Departing Wed, Oct 15, returning Sun, Nov 2.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Montreal Pierre Elliott Trudeau on Wed, Oct 15, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departing from Chicago Midway on Sun, Nov 2, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$366, select.
Chicago.C$369 per passenger.Departing Thu, Nov 13, returning Mon, Nov 17.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Montreal Pierre Elliott Trudeau on Thu, Nov 13, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Mon, Nov 17, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$369, select.
Chicago.C$377 per passenger.Departing Thu, Nov 27, returning Thu, Dec 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Montreal Pierre Elliott Trudeau on Thu, Nov 27, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Thu, Dec 4, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From C$377, 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.
Aug
from C$327
Sep
from C$276
Oct
from C$298
Nov
from C$369
Dec
from C$398
Jan
from C$398
Feb
from C$404
Mar
from C$407
Apr
from C$398
May
from C$417
Jun
from C$416
Jul
from C$416

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 foundC$276
Cheapest month to flySeptember

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

The best price we found for a round-trip flight from Montreal to Chicago Midway is C$276. 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 C$276.
There are no flights flying from Montreal to Chicago Midway, as of August 2025.
The cheapest month to fly from Montreal to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Montreal to Chicago Midway Airport on Thursday, September 4, 2025.
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

  • Montreal-Pierre Elliott Trudeau International Airport (YUL) is Montreal's main airport. Check out your options for reserving a flight from Montreal to Chicago Midway International Airport (MDW) departing from here.

  • Chicago is one hour behind Montreal. Chicago Midway International Airport is located in Chicago, which operates on the UTC-5 timezone.

  • Leave plenty of time to catch your flight from Montreal to MDW. As a rule of thumb, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Peak travel periods mean busier airports, so be there even earlier. Give yourself at least two hours before a domestic flight and four hours for international journeys to stick to your schedule.

Airports in Montreal

Montreal-Pierre Elliott Trudeau International Airport (YUL)

  • Travelling from central Montreal to YUL takes about 45 minutes by public transport. If you ride-share, drive or get a cab, you'll cover the 26 kilometres in 25 minutes or so, depending on traffic.

  • Catching an early flight from Montreal to Chicago Midway International Airport? Avoid the last-minute rush to the terminal (and get some bonus sleep) by staying at one of these hotels near Montreal-Pierre Elliott Trudeau International Airport:

  • When it comes to Montreal-Pierre Elliott Trudeau International Airport's on-time performance, data shows 64.89% of flights complete their journey on time.

  • YUL is located at 975 Romeo Vachon Street North.

St. Hubert Airport (YHU)

  • With public transport, you can travel from central Montreal to YHU in around 1 hour 45 minutes. The airport is roughly 40 kilometres away, and making the trip by car takes approximately 35 minutes.

  • Want to treat yourself to an extra night away before your Montreal to MDW flight? Check in to a hotel near St. Hubert Airport before your break officially begins. These stays are calling your name:

About Chicago Midway International Airport (MDW)

  • Book a hotel close to MDW if you're catching a late flight from Montreal to Chicago Midway International Airport. Settle into one of these options and say goodnight sooner:

  • Travel at your own speed with a Chicago Midway International Airport rental car. Book your wheels from Dollar, Hertz or Budget and venture far and wide through Chicago and beyond.

  • Booking your vehicle around four weeks ahead of your Montreal to Chicago Midway International Airport flight can help you secure the lowest rate.

  • You'll find MDW at 5700 South Cicero.

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

  • Central Chicago is around 14 kilometres from Chicago Midway International Airport. Journey times by car rental or cab will vary depending on traffic conditions, so do a little research before your trip.

  • Travelling on public transport will take you around 45 minutes.

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

  • Currently, C$178 is the best price we've found for a one-way ticket from Montreal to Chicago Midway International Airport. The cheapest price for a return flight is C$276. Remember fares may change due to demand at the time of booking.

  • To find cheap flights from Montreal to MDW, book in advance. Airlines generally offer their most competitively priced fares when flights are first released.

  • If you can be flexible with your travel plans, use the 'Whole month' search tool. It'll show you the lowest price in each month when searching for your Montreal to Chicago Midway International Airport ticket.

  • Stay on top of deals for flight tickets from Montreal to MDW by setting up a Price Alert. We'll send you an email or notification on the app when a new discounted fare appears.

  • Tailor your flights using filters. Select your departure and arrival times, total journey duration and airlines. You can also sort the results by 'Cheapest,' 'Best' or 'Fastest' flights from Montreal to Chicago Midway International Airport.

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

  • May is the quietest month for flights from Montreal to Chicago Midway International Airport (MDW), while July is the most popular. Choose the best time to visit Chicago based on whether you want a laid-back vibe or a lively atmosphere.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Montreal to MDW flight ticket then if that's your ideal forecast.

  • If you'd rather travel in cooler conditions, look for a cheap ticket from Montreal to Chicago Midway International Airport in January when temperatures are between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • Chicago will leave a lasting impression, but there are so many other parts of the United States you should also see. About 257 kilometres south-east of Chicago, a trip to Indianapolis will keep you on the move. Don't miss top attractions like 9-11 Memorial, Lucas Oil Stadium and Eiteljorg Museum.

  • Milwaukee is another well-known destination in the United States and is around 137 kilometres north of Chicago. No trip is complete without experiencing Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County 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.