Cheap Flights from Toronto to Chicago Midway

Compare Toronto 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 to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Toronto to Chicago Midway? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Toronto to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Toronto to Chicago Midway flights are currently cheapest in November.

Direct flights from Toronto to Chicago Midway

Toronto to Chicago Midway: Alternative routes

Compare routes from Toronto 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 found$346
Cheapest month to flyNovember
Average flight time1 hr, 50 mins
Most popular airlinePorter Airlines (Canada) Ltd
Average flights per week32

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

The best price we found for a return flight from Toronto to Chicago Midway is $346. 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 to Chicago Midway.
Porter Airlines (Canada) Ltd, Porter Airlines Inc and Air Transat fly direct from Toronto to Chicago Midway.
As of October 2024, there are 32 flights per week flying from Toronto to Chicago Midway.
The cheapest month to fly from Toronto to Chicago Midway is usually October 2024.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Toronto to Chicago Midway Airport on Thursday, 21 November 2024.
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.
The cheapest airline that flies to Chicago Midway is Porter Airlines (Canada) Ltd .

How to find the best cheap flights from Toronto to Chicago Midway with Skyscanner Flight Search

Whether you’re looking for a one-way or return flight, compare deals on plane tickets from Toronto to Chicago Midway with all major carriers, and find the cheapest fares, using Skyscanner’s Flight Search.

  • Simply hit ‘search’ – our Flight Search tool compares prices from all major online travel agents and airlines that offer flights from Toronto to Chicago Midway to help you find the best and cheapest tickets – with no hidden fees or extra costs

  • Flex your dates – use Skyscanner’s ‘whole month’ tool to find the cheapest time to fly from Toronto to Chicago Midway within your selected dates

  • Find direct flights – tick ‘direct flights only’ to only see direct plane tickets from Toronto to Chicago Midway, if available

  • Search for nearby airports - broaden your search and potentially find even better deals for nearby airports in Toronto and Chicago Midway by selecting "add nearby airports" in the Flight Search tool

  • Book a multi-city trip – planning on visiting more than one location on your journey? Select ‘multi-city’ when searching for flights to find the best deals for stop-overs

  • Choose your flight class – compare prices for economy, business, and first class plane tickets from Toronto to Chicago Midwayand get the best deals however you choose to fly

  • Use airline points – check whether your chosen airline has a points system, such as Airpoints, to unlock flight ticket discounts and make savings on future trips from Toronto to Chicago Midway - and other destinations

Get Price Alerts to keep track of airfare changes

Score the best prices on cheap flights from Toronto to Chicago Midway with Skyscanner’s Price Alerts. Use Flight Search to find flights for your route, then click the “Get Price Alerts” button on the top left of the results page to get a notification to your phone or e-mail whenever ticket prices go up or down. For mobile users, click the bell on the top right. You can also create Price Alerts using the free Skyscanner app.

Plan your trip to Chicago Midway all in one place with hotels and car hire

Discover the best deals on hotels and car hire in Chicago Midway to keep all your bookings in one place and make your journey as smooth as possible. Simply use Skyscanner’s search tool to compare prices from top hotel and car providers across the country, from global to local brands.

Find hotels in Chicago Midway
Find car hire in Chicago Midway

Book flights from Toronto to Chicago Midway with peace of mind

Fly from Toronto to Chicago Midway with peace of mind using Skyscanner’s helpful tips and resources.

  • Find flexible tickets – use Flight Search to book flexible tickets from Toronto to Chicago Midway (with eligible airlines) to protect your money if your flights are changed or cancelled

  • Keep track of travel information– make sure you check the latest travel guidance before you fly to Chicago Midway - including visa requirements, health alerts, and more - to avoid unexpected delays

  • Check your travel insurance – make sure you have the right travel insurance before your trip from Toronto to Chicago Midway to cover you for any unexpected events, such as cancellations, delays, and lost luggage

  • Add travel cost protection - avoid travel pitfalls and choose Travel Cost Protection with Skyscanner when booking flights from Toronto to Chicago Midway. It's available at the checkout for eligible destinations

Make greener choices with sustainable flights from Toronto to Chicago Midway

Did you know that with Skyscanner Flight Search, you can filter flights from Toronto to Chicago Midway to only see routes with lower-than-average carbon emissions? Simply select "Only show flights with lower CO2 emissions" under "Greener choices" in the filter menu, or look for the "Greener Choices" label at the top of flights listings.


Read more about Skyscanner's commitment to sustainable travel

Unlock exclusive deals with the Skyscanner app

Download the free Skyscanner app today and unlock exclusive deals on cheap flights from Toronto to Chicago Midway, car hire, and hotels at anytime, from anywhere.


Download the Skyscanner app today

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