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Cheap Flights from Chicago Midway to Toronto

Compare Chicago Midway to Toronto flight deals

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

Book the best Toronto fare with no extra fees

Flight deals from Chicago Midway to Toronto

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to Toronto? Find the lowest prices on one-way and return tickets right here.
Toronto.R 1,196 per passenger.Departing Tue, 14 Apr.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 14 Apr, arriving in Toronto Island.Price includes taxes and charges.From R 1,196, select.
Toronto.R 1,210 per passenger.Departing Wed, 3 Jun.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Wed, 3 Jun, arriving in Toronto Island.Price includes taxes and charges.From R 1,210, select.
Toronto.R 1,210 per passenger.Departing Tue, 12 May.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 12 May, arriving in Toronto Island.Price includes taxes and charges.From R 1,210, select.
Toronto.R 1,221 per passenger.Departing Fri, 13 Mar.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 13 Mar, arriving in Toronto Island.Price includes taxes and charges.From R 1,221, select.
Toronto.R 1,237 per passenger.Departing Fri, 27 Feb.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 27 Feb, arriving in Toronto Island.Price includes taxes and charges.From R 1,237, select.
Toronto.R 2,262 per passenger.Departing Tue, 7 Jul.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 7 Jul, arriving in Toronto Island.Price includes taxes and charges.From R 2,262, select.
Toronto.R 2,262 per passenger.Departing Thu, 10 Sep.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Thu, 10 Sep, arriving in Toronto Island.Price includes taxes and charges.From R 2,262, select.
Toronto.R 2,262 per passenger.Departing Tue, 10 Nov.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 10 Nov, arriving in Toronto Island.Price includes taxes and charges.From R 2,262, select.

Find the cheapest month to fly from Chicago Midway to Toronto

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Toronto flights are currently cheapest in April.
Feb
from R 1,237
Mar
from R 1,221
Apr
from R 1,196
May
from R 1,210
Jun
from R 1,210
Jul
from R 2,262
Aug
from R 2,266
Sep
from R 2,262
Oct
from R 2,262
Nov
from R 2,262
Dec
from R 2,267
Jan
from R 2,267

Direct flights from Chicago Midway to Toronto

Alternative Chicago Midway to Toronto routes

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

Toronto Island

3km from central Toronto
ClosestCheapest
from R 1,196
Search flights

Toronto Pearson International

20km from central Toronto
from R 1,613
Search flights

John C. Munro Hamilton

70km from central Toronto
from R 11,313
Search flights

Kitchener / Waterloo

83km from central Toronto
from R 5,937
Search flights

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight foundR 1,196
Cheapest month to flyApril
Average flight time1 hr, 42 mins
Most popular airlinePorter Airlines
Average flights per week70

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

There are 4 airports in Toronto: Toronto Island, Toronto Pearson International, John C. Munro Hamilton, and Kitchener / Waterloo.
The best price we found for a return flight from Chicago Midway to Toronto is R 2,881. 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.
1 hour and 42 minutes is the average flight time from Chicago Midway to Toronto.
Porter Airlines, Porter Airlines Inc and Air Transat fly direct from Chicago Midway to Toronto.
As of February 2026, there are 70 flights per week flying from Chicago Midway to Toronto.
The cheapest month to fly from Chicago Midway to Toronto is usually March.
If you're flying from Chicago Midway Airport, the cheapest airport near Toronto is Toronto Island – which is 3.0 km away from the centre of Toronto. We've found flights into this airport from R 2,881.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Toronto on Thursday, 12 March 2026.
Yes – the average flight time is 1 hour and 42 minutes.
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 Toronto 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 Toronto is around 40 days in advance, so don’t leave your flight to the last minute.
In February, the average temperature is usually around -5°C. July is typically the warmest month in Toronto, when it usually averages around 25°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -8°C. The rainiest month is September.
Currently, Porter Airlines offers the cheapest flight tickets to Toronto.

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

  • Chicago Midway International Airport is located in Chicago. Following the UTC-4 timezone, Toronto is one hour ahead of Chicago.

  • With 13 flights a week between the two airports, Chicago Midway International Airport (MDW) to Billy Bishop Toronto City Airport (YTZ) is the busiest route. Porter Airlines operates the earliest flight at 09:15. If you prefer to make the most of your day before you fly, the last flight from MDW to YTZ is with Porter Airlines at 17:50.

  • For stress-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to catch your MDW to Toronto flight.

  • Delays at check-in and security are likely if you're heading away during high season, so allow even more breathing space. A good general rule for peak times? Arrive up to four hours ahead for international flights and at least two hours for domestic departures.

  • You can book a direct Chicago Midway International Airport to Toronto ticket. Start your journey at MDW and end it at Billy Bishop Toronto City Airport (YTZ).

  • Porter Airlines is a popular carrier that operates direct flights from Chicago Midway International Airport to Toronto.

  • We make it simple to book flight tickets from MDW to Toronto with a stopover. To see all the options, deselect 'Direct flights only.' Then, select a flight that has a stop long enough to tour the city of your choice. The most sought-after stopovers include:

    • Minneapolis-St. Paul International Airport (MSP)

    • Detroit Metropolitan Wayne County Airport (DTW)

    • Orlando International Airport (MCO)

  • Located around 14 kilometres from the centre of Chicago, MDW can be reached in about 20 minutes by car (depending on traffic). The journey on public transport will take roughly 45 minutes.

  • Want a relaxed start to your travels? Stay near MDW. Whether you're boarding an early flight from Chicago Midway International Airport to Toronto or just don't want to be rushed, these hotels are just the thing:

  • Of the flights that depart from Chicago Midway International Airport, 77.88% arrive on time at their destination.

  • You'll find MDW at 5700 South Cicero.

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

  • R 1,193 is the cheapest price we've found for a one-way Chicago Midway International Airport to Toronto flight. A return flight ticket right now is R 2,881. Depending on when you book and the availability, these fares may change.

  • Book two months before you want to travel. Research on pricing trends suggests this is the ideal window for finding cheap flights from MDW to Toronto.

  • Plan your trip for June. That's the best month for scoring a bargain on Chicago Midway International Airport to Toronto tickets. If you're open to different travel dates, use the 'Whole month' tool to access the lowest price across every month.

  • You don't need to keep checking in to see if fares have dropped when you create a Price Alert. We'll notify you when there's an even better deal on cheap flights from MDW to Toronto.

  • Select your preferred departure and arrival times, airlines and number of stops with our filters. Then, sort the results for your flight from Chicago Midway International Airport to Toronto by 'Cheapest,' 'Best' or 'Fastest.'

Airports in Toronto

Pearson International Airport (YYZ)

  • Pearson International Airport (YYZ) to the centre of Toronto takes around 25 minutes by car. The centre is roughly 27 kilometres away.

  • Getting there on public transport typically takes 50 minutes.

  • If you're coming in on a late flight from Chicago Midway International Airport to Toronto, nothing beats the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and relaxing soon after at one of these accommodation options near YYZ:

  • Go wherever you want, whenever you want with a Pearson International Airport rental car. Pick up your wheels from Routes Car Rentals, Green Motion or Thrifty and chase adventure across Toronto and beyond.

  • Lock in the best rate by reserving your ride from Pearson International Airport around three weeks in advance of your flight from MDW to Toronto.

Billy Bishop Toronto City Airport (YTZ)

  • Once your flight from Chicago Midway International Airport to Toronto has touched down, you can reach the city centre in around 35 minutes by car. Central Toronto is roughly 3 kilometres from Billy Bishop Toronto City Airport (YTZ).

  • You can expect the journey to take about 40 minutes on public transport.

  • Hang the 'Do not disturb' sign on your door and relax at a hotel near YTZ. Here are a few options where you can put your feet up after your MDW to Toronto flight:

  • The quickest way to reach your destination is with a Billy Bishop Toronto City Airport rental car. Pick up a set of wheels from Hertz, National or Avis and hit the road in a heartbeat.

  • Call dibs on the best options. Booking your ride from YTZ one week in advance often means better prices and a bigger choice of vehicles.

Region of Waterloo International Airport (YKF)

  • Region of Waterloo International Airport (YKF) is about 105 kilometres from the centre of Toronto. It'll take you about 1 hour 15 minutes to reach the city centre in a ride-share or cab once you've hopped off your flight from Chicago Midway International Airport to Toronto.

  • The journey will take about 4 hours 5 minutes when travelling on public transport.

  • If you don't want to make the journey to the centre, find a hotel close to YKF. Make yourself comfortable at one of these options after your MDW to Toronto flight:

  • Take the guesswork out of the next part of your journey by picking up a Region of Waterloo International Airport rental car. Avis, Enterprise and Budget are reliable rental providers.

  • Booking at least a few weeks in advance of your flight from Chicago Midway International Airport to Toronto is always a good idea. As well as better prices, you might find it easier to get the make and model you prefer at YKF.

Best time to go to Toronto

  • Before you book your flights from Chicago Midway International Airport to Toronto, consider which time of year is best for you. Peak season in Toronto offers a bustling atmosphere and plenty of things to do, while the low season brings better deals on hotels and fewer crowds.

  • Book a Chicago Midway International Airport to Toronto flight ticket with a departure in July if you're eager to experience the city during its warmest month. You can expect temperatures to range from 14ºC (57ºF) to 28ºC (82ºF).

  • Search for cheap tickets from MDW to Toronto in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 1ºC (34ºF) on average.

More about Toronto

  • After booking your flight from Chicago Midway International Airport to Toronto, choose a hotel that puts you right where the action is. Make one of these accommodation options your base for exploring Toronto:

  • Royal Ontario Museum and CN Tower are just the start of the major attractions to add to your Toronto itinerary. Continue your sightseeing adventures at Go Tours Canada - Distillery District.

Explore more of Canada

  • Montreal is just one of the many cities in Canada waiting to be explored once you've seen Toronto. Around 499 kilometres away to the north-east, popular attractions include Mount Royal Park, Montreal Botanical Garden and Saint Joseph's Oratory of Mount Royal.

  • Ottawa is another well-known destination in Canada and is around 354 kilometres north-east of Toronto. No journey is complete without dropping by Parliament Hill, Rideau Canal and National Gallery of Canada.

Plan the rest of your trip from Chicago to Toronto

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