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207 € Cheap Flights from Chicago Midway to Toronto Island

Compare Chicago Midway to Toronto Island flight deals

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

Book the best Toronto Island fare with no extra fees

Flight deals from Chicago Midway to Toronto Island

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to Toronto Island? Find the lowest prices on one-way and return tickets right here.
Toronto.207 € per passenger.Departing Wed, 7 Jan, returning Wed, 14 Jan.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Wed, 7 Jan, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Wed, 14 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 207 €, select.
Toronto.220 € per passenger.Departing Tue, 10 Mar, returning Thu, 12 Mar.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 10 Mar, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Thu, 12 Mar, arriving in Chicago Midway.Price includes taxes and charges.From 220 €, select.
Toronto.228 € per passenger.Departing Thu, 2 Oct, returning Sun, 5 Oct.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Thu, 2 Oct, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Sun, 5 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 228 €, select.
Toronto.232 € per passenger.Departing Sun, 25 Jan, returning Sun, 1 Feb.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Sun, 25 Jan, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Sun, 1 Feb, arriving in Chicago Midway.Price includes taxes and charges.From 232 €, select.
Toronto.234 € per passenger.Departing Sat, 11 Oct, returning Sun, 30 Nov.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Sat, 11 Oct, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Sun, 30 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 234 €, select.
Toronto.235 € per passenger.Departing Thu, 27 Nov, returning Mon, 8 Dec.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Thu, 27 Nov, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Mon, 8 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 235 €, select.
Toronto.235 € per passenger.Departing Thu, 6 Nov, returning Sun, 16 Nov.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Thu, 6 Nov, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Sun, 16 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 235 €, select.
Toronto.237 € per passenger.Departing Fri, 5 Dec, returning Mon, 8 Dec.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 5 Dec, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Mon, 8 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 237 €, select.

Find the cheapest month to fly from Chicago Midway to Toronto Island

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Toronto Island flights are currently cheapest in January.
Sep
from 327 €
Oct
from 228 €
Nov
from 235 €
Dec
from 237 €
Jan
from 207 €
Feb
from 287 €
Mar
from 220 €
Apr
from 288 €
May
from 288 €
Jun
from 288 €
Jul
Find prices
Aug
Find prices

Direct flights from Chicago Midway to Toronto Island

Chicago Midway to Toronto Island: Alternative routes

Compare routes from Chicago Midway to Toronto below. You may find an airport to fly into that's cheaper, faster, or easier than Toronto Island.

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight found207 €
Cheapest month to flyJanuary
Average flight time1 hr, 42 mins
Most popular airlinePorter Airlines
Average flights per week38

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

The best price we found for a return flight from Chicago Midway to Toronto Island is 207 €. 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 Island.
Porter Airlines, Porter Airlines Inc and Air Transat fly direct from Chicago Midway to Toronto Island.
As of September 2025, there are 38 flights per week flying from Chicago Midway to Toronto Island.
The cheapest month to fly from Chicago Midway to Toronto Island is usually January.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Toronto Island Airport on Wednesday, 7 January 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 Island 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.
Currently, Porter Airlines offers the cheapest flight tickets to Toronto Island.

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

  • Take a direct flight from Chicago Midway International Airport to Billy Bishop Toronto City Airport and you'll be in the air for an average of 1 hour 40 minutes.

  • Toronto is one hour ahead of Chicago and follows the UTC-4 timezone.

  • Each week, there are 21 Chicago Midway International Airport to Billy Bishop Toronto City Airport flights. If you prefer to take off early, go for the 08:00 Porter Airlines flight. If you're eager to make the most of your day before flying, the last flight is at 17:49 with Porter Airlines.

  • Your MDW to YTZ flight won't wait if you're running late, so get to the airport with time to spare. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • You can expect longer lines during popular months such as July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a smart move.

  • Travelling to Toronto (and then discovering more of Canada!) is a cinch with Porter Airlines. This popular airline offers direct flights from Chicago Midway International Airport to Billy Bishop Toronto City Airport.

  • Porter Airlines is the airline with the highest passenger demand for this route.

  • Porter Airlines is the most punctual carrier that offers MDW to YTZ flights, with 71.11% of its services arriving on schedule.

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Billy Bishop Toronto City Airport (YTZ)

  • The lowest price we've found for a one-way Chicago Midway International Airport to Billy Bishop Toronto City Airport flight is 63 €. A return ticket is currently 207 €. Depending on the availability and when you book, these fares may change.

  • Score cheap tickets from MDW to YTZ by booking seven months ahead. Based on our research, that's the sweet spot for landing a bargain.

  • Schedule your trip for June. That's the cheapest month for flights from Chicago Midway International Airport to Billy Bishop Toronto City Airport. If you're flexible on when you fly, try out the 'Whole month' tool to find the cheapest price across every month.

  • Spend less time searching for cheap flights from MDW to YTZ by setting up a Price Alert. You'll receive an email or push notification on the app when fares go down.

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

Handy information about Chicago Midway International Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway International Airport, 77.88% of flights stick to their scheduled arrival time.

  • Central Chicago to Chicago Midway International Airport is around 19 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're ride-sharing, catching a cab or driving.

  • Planning to catch public transport? Expect a trip time of around 45 minutes.

  • Get your travels off to a stress-free start by staying near MDW. Whether you're taking an early flight from Chicago Midway International Airport to Billy Bishop Toronto City Airport or just don't like being rushed, these hotels are the answer:

Arriving at Billy Bishop Toronto City Airport (YTZ)

  • If you have a late Chicago Midway International Airport to Billy Bishop Toronto City Airport flight, few things beat the convenience of staying near the terminal. Pick up your bags from the carousel and then be resting not long after at one of these accommodation options near YTZ:

  • Travel at your own pace with a Billy Bishop Toronto City Airport rental car. Book your wheels from Hertz, National or Avis and find adventure across Toronto and beyond.

  • Lock in the lowest price by reserving your vehicle from Billy Bishop Toronto City Airport about one week before your trip.

Getting from Billy Bishop Toronto City Airport (YTZ) to central Toronto

  • From Billy Bishop Toronto City Airport, Toronto is approximately 3 kilometres away. It takes around 35 minutes to reach the centre by car.

  • It typically takes 40 minutes if you're travelling by public transport.

When to fly to Billy Bishop Toronto City Airport (YTZ)

  • July is the most popular month for flights from Chicago Midway International Airport to Billy Bishop Toronto City Airport. To steer clear of the crowds, travel to Toronto in February.

  • When booking your flight from Chicago Midway International Airport to Billy Bishop Toronto City Airport, consider the kind of weather you like. July is the warmest month in Toronto, with temperatures ranging from 14ºC (57ºF) to 28ºC (82ºF).

  • If you'd rather travel in cooler conditions, search for a cheap ticket from MDW to YTZ in January. Temperatures average between -12ºC (10ºF) and 1ºC (34ºF) then.

Explore more of Canada

  • You've seen Toronto, now it's time to explore more of Canada. Travel around 499 kilometres north-east to Montreal to check off its top sights. From Mount Royal Park to Montreal Botanical Garden and Saint Joseph's Oratory of Mount Royal, you've got a jam-packed schedule ahead.

  • If you want to check out another corner of Canada, head for Ottawa, about 354 kilometres north-east of Toronto. Parliament Hill, Rideau Canal and National Gallery of Canada are among the biggest draws.

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.