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Cheap flights from Toronto Island to Chicago Midway

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Compare Toronto Island to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Toronto Island to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Toronto Island to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.P5,934 per passenger.Departing Fri, 20 Jun, returning Mon, 23 Jun.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Fri, 20 Jun, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Mon, 23 Jun, arriving in Toronto Island.Price includes taxes and charges.From P5,934, select.
Chicago.P6,159 per passenger.Departing Tue, 23 Sep, returning Sun, 28 Sep.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue, 23 Sep, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sun, 28 Sep, arriving in Toronto Island.Price includes taxes and charges.From P6,159, select.
Chicago.P7,027 per passenger.Departing Fri, 7 Nov, returning Fri, 7 Nov.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Fri, 7 Nov, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 7 Nov, arriving in Toronto Island.Price includes taxes and charges.From P7,027, select.
Chicago.P7,027 per passenger.Departing Sun, 16 Nov, returning Sun, 7 Dec.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sun, 16 Nov, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sun, 7 Dec, arriving in Toronto Island.Price includes taxes and charges.From P7,027, select.
Chicago.P7,027 per passenger.Departing Thu, 23 Oct, returning Tue, 4 Nov.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 23 Oct, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 4 Nov, arriving in Toronto Island.Price includes taxes and charges.From P7,027, select.
Chicago.P7,027 per passenger.Departing Tue, 2 Dec, returning Sun, 7 Dec.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue, 2 Dec, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sun, 7 Dec, arriving in Toronto Island.Price includes taxes and charges.From P7,027, select.
Chicago.P7,036 per passenger.Departing Sat, 18 Oct, returning Wed, 22 Oct.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 18 Oct, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Wed, 22 Oct, arriving in Toronto Island.Price includes taxes and charges.From P7,036, select.
Chicago.P7,491 per passenger.Departing Thu, 11 Sep, returning Thu, 2 Oct.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 11 Sep, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Thu, 2 Oct, arriving in Toronto Island.Price includes taxes and charges.From P7,491, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Toronto Island to Chicago Midway flights are currently cheapest in June.
May
from P20,492
Jun
from P5,934
Jul
from P8,888
Aug
from P9,714
Sep
from P6,159
Oct
from P7,036
Nov
from P7,027
Dec
from P7,027
Jan
from P19,484
Feb
Find prices
Mar
Find prices
Apr
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Direct flights from Toronto Island to Chicago Midway

Toronto Island to Chicago Midway: Alternative routes

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

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight foundP5,934
Cheapest month to flyJune
Average flight time1 hr, 50 mins
Most popular airlinePorter Airlines
Average flights per week37

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

The best price we found for a return flight from Toronto Island to Chicago Midway is P5,934. 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 50 minutes is the average flight time from Toronto Island to Chicago Midway.
Porter Airlines, Porter Airlines Inc and Air Transat fly direct from Toronto Island to Chicago Midway.
As of May 2025, there are 37 flights per week flying from Toronto Island to Chicago Midway.
The cheapest month to fly from Toronto Island to Chicago Midway is usually May 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Toronto Island Airport to Chicago Midway Airport on Friday, 20 June 2025.
Yes – the average flight time is 1 hour and 50 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • Book a direct flight from Billy Bishop Toronto City Airport to Chicago Midway International Airport and you'll be travelling for an average of 1 hour 50 minutes.

  • Chicago is one hour behind Toronto and is in the UTC-5 timezone.

  • Choose from 43 weekly Billy Bishop Toronto City Airport to Chicago Midway International Airport flights. The 09:20 departure with Porter Airlines is the earliest available. Porter Airlines operates the last service of the day at 21:35.

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

  • You'll likely experience longer queues in popular months like July. Arriving up to four hours ahead of international flights and two hours for domestic departures is a smart move.

  • Porter Airlines has direct flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport. Book with this popular carrier, then get ready to discover the sights in Chicago — and maybe even more of United States if time allows.

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

  • With 69.15% of services landing as planned, Porter Airlines is the most punctual carrier operating YTZ to MDW flights.

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

  • Right now, P4,472 is the cheapest price we've found for a one-way Billy Bishop Toronto City Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is P5,934. Remember that fares can change due to availability at the time of booking.

  • To score cheap tickets from YTZ to MDW, reserve your journey six months before your departure.

  • May is the cheapest month for flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport. If you prefer to travel during a different time of year, the 'Whole month' tool will show you the lowest airfares for every month.

  • Stay on top of deals for cheap flights from YTZ to MDW by setting up a Price Alert. You'll receive an email or notification through the app when a new low fare is offered.

  • Discover the right flight for you with the help of the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter results by airline, departure and arrival times, and number of stops.

Handy information about Billy Bishop Toronto City Airport (YTZ)

  • Of the flights that depart from Billy Bishop Toronto City Airport, 62.09% land on time at their destination.

  • Billy Bishop Toronto City Airport is about 3 kilometres from central Toronto. If you're catching a cab, ride-sharing or driving from the centre, it'll take you 35 minutes or so to get there, depending on the traffic.

  • You can expect a trip time of roughly 40 minutes on public transport.

  • Get your break off to a relaxed start by staying near YTZ. Whether you've booked an early flight from Billy Bishop Toronto City Airport to Chicago Midway International Airport or just don't like being rushed, these stays are the answer:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you want is a lengthy journey to your hotel if you're landing late on a Billy Bishop Toronto City Airport to Chicago Midway International Airport flight. Reserve one of these accommodation options near MDW instead:

  • Hit the road running by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's usual tourist stops.

  • Lock in the best possible rate by reserving your ride from Chicago Midway International Airport around four weeks before your departure date.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport to central Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

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

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Billy Bishop Toronto City Airport to Chicago Midway International Airport is May, while July is the busiest. Pick the best time to go to Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.

  • Lock in your flight from Billy Bishop Toronto City Airport to Chicago Midway International Airport for July if you'd like to visit Chicago during its warmest month. You can expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from YTZ to MDW around that time if you like travelling in cooler conditions.

Explore more of United States

  • You've visited Chicago, now it's time to explore other parts of United States. Journey around 451 kilometres south-east to Columbus to check off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you on the go.

  • Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Toronto to Chicago

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