Skyscanner home

Cheap Flights from Chicago Midway to Montreal

Compare Chicago Midway to Montreal flight deals

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

Book the best Montreal fare with no extra fees

Flight deals from Chicago Midway to Montreal

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Montreal? If you want to travel next month, return fares start from R 4,407. Find the lowest prices on one-way and return tickets right here.
Montreal.R 1,989 per passenger.Departing Tue, 20 Oct.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Tue, 20 Oct, arriving in Montreal St Hubert.Price includes taxes and charges.From R 1,989, select.
Montreal.R 2,125 per passenger.Departing Tue, 15 Sep.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Tue, 15 Sep, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 2,125, select.
Montreal.R 2,188 per passenger.Departing Wed, 26 Aug.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Wed, 26 Aug, arriving in Montreal St Hubert.Price includes taxes and charges.From R 2,188, select.
Montreal.R 2,323 per passenger.Departing Tue, 12 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 12 Jan, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 2,323, select.
Montreal.R 2,490 per passenger.Departing Sat, 7 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 7 Nov, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 2,490, select.
Montreal.R 2,520 per passenger.Departing Thu, 17 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 17 Dec, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 2,520, select.
Montreal.R 2,725 per passenger.Departing Tue, 23 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 23 Mar, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 2,725, select.
Montreal.R 2,736 per passenger.Departing Tue, 25 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 25 May, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 2,736, select.
Montreal.R 2,748 per passenger.Departing Mon, 19 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 19 Apr, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 2,748, select.
Montreal.R 3,229 per passenger.Departing Thu, 10 Jun.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 10 Jun, arriving in Montreal Pierre Elliott Trudeau.Price includes taxes and charges.From R 3,229, select.

Find the cheapest month to fly from Chicago Midway to Montreal

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Montreal flights are currently cheapest in October.
Aug
from R 2,188
Sep
from R 2,125
Oct
from R 1,989
Nov
from R 2,490
Dec
from R 2,520
Jan
from R 2,323
Feb
Find prices
Mar
from R 2,725
Apr
from R 2,748
May
from R 2,736
Jun
from R 3,229
Jul
Find prices

Alternative Chicago Midway to Montreal routes

Looking for the cheapest, fastest or easiest route from Chicago Midway to Montreal? You could fly into the following airports instead.

Montreal St Hubert

11km from central Montreal
ClosestCheapest
from R 1,988
Search flights

Montreal Pierre Elliott Trudeau

16km from central Montreal
from R 2,125
Search flights

Chicago to Montreal: Flight information

The things to know before you go.
Cheapest flight foundR 1,989
Cheapest month to flyOctober

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

There are 2 airports in Montreal: Montreal St Hubert and Montreal Pierre Elliott Trudeau.
The best price we found for a return flight from Chicago Midway to Montreal is R 4,405. 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 Chicago Midway to Montreal. But we found flights with one or more stops from R 4,405.
As of August 2026, there are no flights flying from Chicago Midway to Montreal.
The cheapest month to fly from Chicago Midway to Montreal is usually September.
If you're flying from Chicago Midway Airport, the cheapest airport near Montreal is Montreal Pierre Elliott Trudeau – which is 16.1 km away from the centre of Montreal. We've found flights into this airport from R 4,405.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Montreal on Wednesday, 16 September 2026.
No airlines currently offer direct flights between Chicago Midway Airport and Montreal. 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 Montreal 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 Montreal is around 40 days in advance, so don’t leave your flight to the last minute.

In August, the average temperature is usually around 20°C. July is typically the warmest month in Montreal, when it usually averages around 25°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -17°C. The rainiest month is June.
Currently, Porter Airlines offers the cheapest flight tickets to Montreal.

Travelling from Chicago Midway International Airport (MDW) to Montreal: what you need to know

  • Montreal is one hour ahead of Chicago, where Chicago Midway International Airport is located. Montreal runs on the UTC-5 timezone.

  • To avoid rushing for your MDW to Montreal flight, allow plenty of time for things like check-in and baggage drop. Turning up two hours before international departures and an hour before domestic flights is the general rule.

  • Be prepared for longer lines during popular months like July. Arriving up to four hours in advance for international flights and two hours for a domestic departure is a wise move.

  • Stopovers are the perfect opportunity to break up your journey and possibly even explore a different city. When browsing for plane tickets from MDW to Montreal, deselect the 'Direct flights only' box to see where you can visit along the way. Popular options include:

    • New York LaGuardia Airport (LGA)

    • Detroit Metropolitan Wayne County Airport (DTW)

    • Philadelphia International Airport (PHL)

  • Travelling from central Chicago to MDW takes around 30 minutes on public transport. If you ride-share, drive or get a taxi, you'll cover the 14 kilometres in 25 minutes or so, depending on traffic conditions.

  • Looking for a hotel close to MDW? If you're boarding an early flight from Chicago Midway International Airport to Montreal, these accommodation options will put you moments from check-in:

  • When it comes to Chicago Midway International Airport's on-time performance, 76% of flights stick to their scheduled arrival time.

  • The address for MDW is 5700 South Cicero.

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

  • R 1,988 is the cheapest price we've found for a one-way Chicago Midway International Airport to Montreal flight. A round-trip ticket right now is R 4,407. Depending on when you want to go and the availability, these fares could change.

  • To pick up cheap flights from MDW to Montreal, book as early as possible. Airlines typically offer lower prices when tickets first go on sale.

  • If you're willing to be flexible with your travel dates, check out the 'Whole month' tool. It'll show you the lowest price across each month when looking for your Chicago Midway International Airport to Montreal ticket.

  • You don't need to keep looking every day to see if fares have dropped when you create a Price Alert. We'll update you when there's an updated deal for cheap flights from MDW to Montreal.

  • Snag an affordable flight from Chicago Midway International Airport to Montreal with the help of our filters. Select your ideal duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Montreal

Montreal-Trudeau International Airport (YUL)

  • Montreal-Trudeau International Airport (YUL) to central Montreal takes around 25 minutes to reach by car. The centre is roughly 19 kilometres away.

  • If you're taking public transport, expect a journey time of about 45 minutes.

  • Book a hotel close to YUL if you have a late flight from Chicago Midway International Airport to Montreal. Pick one of these options and make your first night all about rest:

  • Reserving your ride from Montreal-Trudeau International Airport about four weeks in advance of your flight from MDW to Montreal can help you get the lowest rate.

  • The street address for YUL is 975 Romeo Vachon Street North.

Montreal Metropolitan Airport (YHU)

  • Once your flight from Chicago Midway International Airport to Montreal has arrived, you can get to the city centre in about 25 minutes by car. Central Montreal is roughly 23 kilometres from Montreal Metropolitan Airport (YHU).

  • The journey will take about 1 hour on public transport.

  • Hang the 'Do not disturb' sign on your door and unwind at a hotel close to YHU. Here are a few options where you can kick back after your MDW to Montreal flight:

  • Get the vehicle you prefer, not just whatever's left, by reserving your ride from YHU in advance. You'll also avoid last-minute price hikes, especially when the airport is busy.

Best time to go to Montreal

  • It's time to plan your dates for your flight from Chicago Midway International Airport to Montreal. July is the most popular month to visit Montreal. If you like a more relaxed atmosphere, go in January.

  • Book a Chicago Midway International Airport to Montreal plane ticket with a departure in July to experience the city during its warmest month. You can expect temperatures to range from 14ºC (57ºF) to 28ºC (82ºF).

  • Look for cheap tickets from MDW to Montreal in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -19ºC (-2ºF) and -2ºC (28ºF) on average.

More about Montreal

  • When it comes to searching for somewhere to rest your head, you'll find the top stays in Montreal right here. Check out these options as soon as you've locked in your flight from Chicago Midway International Airport to Montreal:

  • Every great journey has to include some sightseeing. Montreal Botanical Garden, Cirque du Soleil - KURIOS and Saint Joseph's Oratory of Mount Royal are must-do's during your Montreal adventure.

Explore more of Canada

  • Toronto is just one of the many places in Canada waiting to be explored once you've seen Montreal. Around 499 kilometres away to the southwest, its best attractions include CN Tower, The Top CN Tower and Royal Ontario Museum.

  • If you want to check out another well-known destination in Canada, head for Ottawa, about 153 kilometres west of Montreal. Rideau Canal National Historic Site, Parliament Hill and Rideau Canal, Locks 1 - 8 - Ottawa are the start of reasons to visit.

Plan the rest of your trip from Chicago to Montreal

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