C$292 Cheap Flights from Chicago Midway (MDW) to Toronto (YTOA)

Compare Chicago Midway to Toronto flight deals

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Flight deals from Chicago Midway to Toronto

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Toronto? If you want to travel next month, return fares start from C$292. Find the lowest prices on one-way and return tickets right here.

Toronto.C$120 per passenger.Departing Tue., Jun. 23.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Tue., Jun. 23, arriving in Toronto Island.Price includes taxes and charges.From C$120, select.

Toronto.C$159 per passenger.Departing Thu., Jul. 16.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Thu., Jul. 16, arriving in Toronto Island.Price includes taxes and charges.From C$159, select.

Toronto.C$160 per passenger.Departing Wed., Aug. 12.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Wed., Aug. 12, arriving in Toronto Island.Price includes taxes and charges.From C$160, select.

Toronto.C$186 per passenger.Departing Tue., Dec. 8.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue., Dec. 8, arriving in Toronto Pearson International.Price includes taxes and charges.From C$186, select.

Toronto.C$186 per passenger.Departing Sat., Oct. 10.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat., Oct. 10, arriving in Toronto Pearson International.Price includes taxes and charges.From C$186, select.

Toronto.C$186 per passenger.Departing Sat., Nov. 21.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat., Nov. 21, arriving in Toronto Pearson International.Price includes taxes and charges.From C$186, select.

Toronto.C$202 per passenger.Departing Mon., Sep. 7.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon., Sep. 7, arriving in Toronto Pearson International.Price includes taxes and charges.From C$202, select.

Toronto.C$301 per passenger.Departing Sun., May 31.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Sun., May 31, arriving in Toronto Island.Price includes taxes and charges.From C$301, select.

Toronto.C$303 per passenger.Departing Wed., Mar. 3.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed., Mar. 3, arriving in Toronto Pearson International.Price includes taxes and charges.From C$303, select.

Toronto.C$303 per passenger.Departing Mon., Jan. 4.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon., Jan. 4, arriving in Toronto Pearson International.Price includes taxes and charges.From C$303, select.

Toronto.C$303 per passenger.Departing Tue., Feb. 9.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue., Feb. 9, arriving in Toronto Pearson International.Price includes taxes and charges.From C$303, 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 June.

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Which airlines fly 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.

Chicago to Toronto: Flight information

The things to know before you go.

Cheapest flight found	C$120
Cheapest month to fly	June
Average flight time	1 hr, 33 mins
Most popular airline	Porter Airlines
Average flights per week	34

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

How many airports are there in Toronto?

There are 4 airports in Toronto: Toronto Island, Toronto Pearson International, John C. Munro Hamilton, and Kitchener / Waterloo.

How much are return flights from Chicago Midway to Toronto?

The best price we found for a return flight from Chicago Midway to Toronto is C$292. 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.

How long does it take to fly from Chicago Midway to Toronto?

1 hour and 32 minutes is the average flight time from Chicago Midway to Toronto.

Which airlines fly direct from Chicago Midway to Toronto?

Porter Airlines, Porter Airlines Inc and Air Transat fly direct from Chicago Midway to Toronto.

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

As of May 2026, there are 34 flights per week flying from Chicago Midway to Toronto.

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

The cheapest month to fly from Chicago Midway to Toronto is usually June.

Which is the cheapest airport to fly into in Toronto?

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 C$292.

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

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, June 4, 2026.

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

Yes – the average flight time is 1 hour and 32 minutes.

How can I get the best flight deal from Chicago Midway Airport to Toronto?

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.

When is the best time to book flights to Toronto?

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.

What’s the weather like in Toronto?

In May, the average temperature is usually around 12°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.

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

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. Operating on the UTC-4 timezone, Toronto is 1 hour ahead of Chicago.
With 21 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 (Canada) Ltd operates the earliest flight at 08:00. If you'd like to make the most of your day before taking off, the last flight from MDW to YTZ is with Porter Airlines (Canada) Ltd at 17:49.
Leave enough time to make your flight from MDW to Toronto. A good rule of thumb is to arrive at least two hours before international departures and an hour ahead for domestic flights.
If you're going away during a peak month like July, be at the airport even earlier. It's wise to arrive up to four hours before an international flight and two hours ahead of domestic departures. Check-in and security lines will be longer during vacation periods like summer and spring break.
You can catch a direct flight from Chicago Midway International Airport to Toronto that lands at Billy Bishop Toronto City Airport (YTZ).
Check out the deals with Porter Airlines (Canada) Ltd. This airline operates direct flights from Chicago Midway International Airport to Toronto.
Consider adding a stopover to possibly find a cheaper flight from MDW to Toronto. Just deselect 'Direct flights only' when searching for the departures. Take a break from travelling at one of these popular options:
- Orlando International Airport (MCO)
- Tampa International Airport (TPA)
- Lambert-St. Louis International Airport (STL)
You can travel to Canada for tourism purposes without a visa if you hold a passport from United States. But before reserving your flight tickets from Chicago Midway International Airport to Toronto, make sure you have the latest information. Visa rules are subject to change, and you may need some travel documentation if your trip is for business or another reason.
Located around 19 kilometres from central Chicago, MDW can be reached in approximately 21 minutes by car (depending on traffic). The journey by public transport takes roughly 46 minutes.
Planning to catch an early flight from Chicago Midway International Airport to Toronto? Avoid the stress of rushing to the terminal (and get some extra shut-eye) by picking one of these hotels near MDW:

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

The best price we've found for a one-way ticket from Chicago Midway International Airport to Toronto is C$120. The cheapest price for a return flight is C$292. Keep in mind fares may change due to availability at the time of booking.
Score cheap tickets from MDW to Toronto by booking at least 10 months ahead. Based on our research, that's the sweet spot for finding a bargain.
June is the cheapest month for tickets from Chicago Midway International Airport to Toronto. If you'd like to travel at a different time of year, the 'Whole month' tool will show you the lowest prices across every month.
Getting a cheap ticket from MDW to Toronto is a piece of cake with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know as soon as the price has dropped.
Tailor your travel plans with filters. Select your preferred arrival and departure times, airlines and total journey duration. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Chicago Midway International Airport to Toronto.

Airports in Toronto

Pearson International Airport (YYZ)

Pearson International Airport (YYZ) to central Toronto takes around 26 minutes by car. It's approximately 27 kilometres away.
If you're using public transport, expect a journey time of roughly 49 minutes.
The last thing you want is a long journey to your hotel if you're getting in late on a flight from Chicago Midway International Airport to Toronto. Book one of these accommodation options near YYZ instead:

Billy Bishop Toronto City Airport (YTZ)

Billy Bishop Toronto City Airport (YTZ) is about 3 kilometres from the centre of Toronto. After your flight from Chicago Midway International Airport to Toronto, it'll take you around 35 minutes to get to the heart of the city in a cab or ride-share.
Public transport will get you there in around 39 minutes.
After your flight from MDW to Toronto, tuck yourself in at a hotel close to YTZ. These are some great options that'll help you slip into relaxation mode:

Best time to go to Toronto

August is the most popular month for flights from Chicago Midway International Airport to Toronto. To escape the crowds, travel to Toronto in February when it's quieter.
Before you book a flight from Chicago Midway International Airport to Toronto, think about the type of weather you enjoy. July is the warmest month in Toronto, with temperatures ranging from 14ºC to 28ºC.
January sees average temperatures of between -12ºC and 1ºC. Look for cheap flights from MDW to Toronto sometime around then if you like travelling in cooler conditions.

More about Toronto

Once you've booked your flight from Chicago Midway International Airport to Toronto, think about where to rest your head in this city. Make one of these accommodation options your base for exploring Toronto:
There are so many things to see and do in this city it can be hard to figure out where to begin. CN Tower, Royal Ontario Museum and Go Tours Canada - Distillery District are highlights which should be on every Toronto itinerary.

Complete your Toronto trip with a car rental

Select one of our car rentals in Toronto and see the sights in your own time. Easily compare rates in one place to find the ideal ride once you've locked in your hotel and cheap flights from Chicago Midway International Airport to Toronto.