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Cheap Flights from Chicago Midway (MDW) to Toronto (YTOA)

Compare Chicago Midway to Toronto flight deals

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

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Flight deals from Chicago Midway Airport 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 £127. Find the lowest prices on one-way and return tickets right here.
Toronto.£53 per passenger.Departing Wed, 6 May.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Wed, 6 May, arriving in Toronto Island.Price includes taxes and charges.From £53, select.
Toronto.£53 per passenger.Departing Fri, 31 Jul.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 31 Jul, arriving in Toronto Island.Price includes taxes and charges.From £53, select.
Toronto.£54 per passenger.Departing Fri, 5 Jun.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 5 Jun, arriving in Toronto Island.Price includes taxes and charges.From £54, select.
Toronto.£55 per passenger.Departing Fri, 7 Aug.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 7 Aug, arriving in Toronto Island.Price includes taxes and charges.From £55, select.
Toronto.£57 per passenger.Departing Tue, 28 Apr.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 28 Apr, arriving in Toronto Island.Price includes taxes and charges.From £57, select.
Toronto.£74 per passenger.Departing Wed, 2 Sep.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 2 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From £74, select.
Toronto.£80 per passenger.Departing Sat, 3 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 3 Oct, arriving in Toronto Pearson International.Price includes taxes and charges.From £80, select.
Toronto.£81 per passenger.Departing Wed, 9 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 9 Dec, arriving in Toronto Pearson International.Price includes taxes and charges.From £81, select.
Toronto.£81 per passenger.Departing Mon, 30 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 30 Nov, arriving in Toronto Pearson International.Price includes taxes and charges.From £81, select.
Toronto.£146 per passenger.Departing Wed, 6 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 6 Jan, arriving in Toronto Pearson International.Price includes taxes and charges.From £146, 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 May.
Apr
from £57
May
from £53
Jun
from £54
Jul
from £53
Aug
from £55
Sep
from £74
Oct
from £80
Nov
from £81
Dec
from £81
Jan
from £146
Feb
Find prices
Mar
Find prices

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

2 miles from central Toronto
ClosestCheapest
from £53
Search flights

Toronto Pearson International

13 miles from central Toronto
from £70
Search flights

John C. Munro Hamilton

43 miles from central Toronto
from £203
Search flights

Kitchener / Waterloo

52 miles from central Toronto
from £139
Search flights

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight found£53
Cheapest month to flyMay
Average flight time1 hr, 41 mins
Most popular airlinePorter Airlines
Average flights per week38

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 £127. 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 41 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 April 2026, there are 38 flights per week flying from Chicago Midway to Toronto.
The cheapest month to fly from Chicago Midway to Toronto is usually May.
If you're flying from Chicago Midway Airport, the cheapest airport near Toronto is Toronto Island – which is 1.8 miles away from the centre of Toronto. We've found flights into this airport from £127.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Toronto on Wednesday, 13 May 2026.
Yes – the average flight time is 1 hour and 41 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 April, the average temperature is usually around 6°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.

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

  • Toronto is one hour ahead of Chicago, where Chicago Midway International Airport is located. Toronto observes the UTC-5 timezone.

  • The most popular route is from Chicago Midway International Airport (MDW) to Billy Bishop Toronto City Airport (YTZ). There are 12 services every week between these two airports. If you'd like to take off as soon as possible, the earliest flight from MDW to YTZ is the 09:15 Porter Airlines service. If you prefer to leave later in the day, the final departure is at 17:50 with Porter Airlines.

  • Give yourself plenty of time to get on your MDW to Toronto flight. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.

  • Be prepared for longer lines during popular months such as July. Arriving up to four hours ahead of international flights and two hours for a domestic departure will give you plenty of time for security and boarding.

  • Direct Chicago Midway International Airport to Toronto tickets are available for booking. Billy Bishop Toronto City Airport (YTZ) is where you'll be touching down.

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

  • A stopover is the perfect opportunity to break up your trip and possibly even tick off a new city. When browsing for plane tickets from MDW to Toronto, deselect the 'Direct flights only' box to see where you can visit along the way. Here are some options to consider:

    • Orlando International Airport (MCO)

    • Minneapolis-Saint Paul International Airport (MSP)

    • Detroit Metropolitan Wayne County Airport (DTW)

  • Travelling from central Chicago to MDW takes around 30 minutes by public transport. If you ride-share, drive or get a taxi, you'll cover the 14 kms (9 miles) in 25 minutes or so, depending on traffic conditions.

  • Booked an early flight from Chicago Midway International Airport to Toronto? Avoid the stress of rushing to the terminal (and sneak in some extra precious sleep) by choosing one of these stays near MDW:

  • When it comes to the on-time performance of Chicago Midway International Airport, data shows 76% of flights arrive within the scheduled time frame.

  • You'll find MDW at 5700 South Cicero.

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

  • The best price we've found for a one-way Chicago Midway International Airport to Toronto flight is £53. The cheapest price for a return flight is £127. Bear in mind fares may change due to demand at the time of booking.

  • To score cheap flights from MDW to Toronto, reserve your journey one month before your planned departure.

  • June is the best month for picking up an amazing deal on Chicago Midway International Airport to Toronto tickets. If you're looking to travel at a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • There's no need to check back constantly to find out if fares have dropped when you set up a Price Alert. We'll notify you as soon as there's an updated deal for cheap flights from MDW to Toronto.

  • Tailor your trip with filters. Choose your ideal departure and arrival times, airlines and total journey duration. You can also sort results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago Midway International Airport to Toronto.

Airports in Toronto

Toronto Pearson International Airport (YYZ)

  • Toronto Pearson International Airport (YYZ) to the centre of Toronto takes about 30 minutes by car. The centre is roughly 27 kms (17 miles) away.

  • If you're travelling by public transport, expect a journey time of around 25 minutes.

  • If you're arriving on a late flight from Chicago Midway International Airport to Toronto, few things beat the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and resting not long after at one of these hotels near YYZ:

  • To lock in the lowest price, reserve your ride from Toronto 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 hit the tarmac, you can get to the city centre in around 10 minutes by car. Central Toronto is roughly 3 kms (2 miles) from Billy Bishop Toronto City Airport (YTZ).

  • The journey will take roughly 20 minutes on public transport.

  • There are some comfortable places to drop your things at near YTZ. Kick back and get cosy after your MDW to Toronto flight at any of these perfectly located options:

  • Lock in the lowest price by reserving your ride from YTZ one week in advance. You can also expect to have a greater selection of vehicles.

John C. Munro Hamilton International Airport (YHM)

  • Head to the city centre after your flight from Chicago Midway International Airport to Toronto has arrived. Central Toronto is around 72 kms (45 miles) from John C. Munro Hamilton International Airport (YHM) and takes roughly 1 hour 10 minutes to reach by taxi or ride-share.

  • Public transport can take you there in about 1 hour 50 minutes.

  • If you don't want to make the trip into the centre, find a hotel near YHM. Get comfortable at one of these options after your MDW to Toronto flight:

  • If you're looking for a specific make or model, booking early increases your chances of getting what you want. Book your ride from YHM a couple of weeks ahead of your flight from Chicago Midway International Airport to Toronto.

Best time to go to Toronto

  • July is the busiest month for flights from Chicago Midway International Airport to Toronto. To steer clear of the crowds, visit Toronto in January.

  • Before booking a Chicago Midway International Airport to Toronto plane ticket, think about what kind of weather you prefer. July is the warmest month in Toronto, with temperatures ranging from 15ºC to 28ºC.

  • Search for cheap tickets from MDW to Toronto in February if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -15ºC and 3ºC on average.

More about Toronto

  • Once you've booked your flight from Chicago Midway International Airport to Toronto, find a hotel that keeps you close to what you want to see. Make one of these options your base for exploring Toronto:

  • There are so many things to see and do in this city it can be hard to know where to start. The Top CN Tower, CN Tower and Royal Ontario Museum are highlights which should be on any well-planned Toronto itinerary.

Explore more of Canada

  • Montreal is just one of the many places in Canada waiting to be discovered after you've experienced Toronto. Around 499 kms (310 miles) away to the northeast, popular attractions include Cirque du Soleil - KURIOS, Montreal Botanical Garden and Saint Joseph's Oratory of Mount Royal.

  • If you want to check out another major stop in Canada, consider Ottawa, roughly 354 kms (220 miles) northeast of Toronto. Rideau Canal National Historic Site, Parliament Hill and Rideau Canal, Locks 1 - 8 - Ottawa are key reasons to visit.

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.