Skyscanner

Cheap flights from Toronto to Chicago Midway

Travelers and cabin class

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 round-trip flight from Toronto to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$184 per passenger.Departing Sat, Jun 7, returning Tue, Jun 10.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Sat, Jun 7, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Tue, Jun 10, arriving in Toronto Island.Price includes taxes and charges.From C$184, select.
Chicago.C$185 per passenger.Departing Mon, Jun 23, returning Mon, Jul 7.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Mon, Jun 23, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Mon, Jul 7, arriving in Toronto Island.Price includes taxes and charges.From C$185, select.
Chicago.C$186 per passenger.Departing Wed, Jul 2, returning Sat, Jul 5.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Wed, Jul 2, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Sat, Jul 5, arriving in Toronto Island.Price includes taxes and charges.From C$186, select.
Chicago.C$187 per passenger.Departing Mon, May 19, returning Wed, May 21.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Mon, May 19, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Wed, May 21, arriving in Toronto Island.Price includes taxes and charges.From C$187, select.
Chicago.C$189 per passenger.Departing Fri, Jul 25, returning Sat, Aug 2.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Fri, Jul 25, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Sat, Aug 2, arriving in Toronto Island.Price includes taxes and charges.From C$189, select.
Chicago.C$193 per passenger.Departing Thu, May 22, returning Sat, Jun 14.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Thu, May 22, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Sat, Jun 14, arriving in Toronto Island.Price includes taxes and charges.From C$193, select.
Chicago.C$199 per passenger.Departing Thu, Sep 11, returning Mon, Sep 15.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Thu, Sep 11, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Mon, Sep 15, arriving in Toronto Island.Price includes taxes and charges.From C$199, select.
Chicago.C$202 per passenger.Departing Sat, Aug 16, returning Wed, Aug 20.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Sat, Aug 16, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Wed, Aug 20, arriving in Toronto Island.Price includes taxes and charges.From C$202, select.

When is the cheapest time 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 June.
Apr
from C$722
May
from C$187
Jun
from C$184
Jul
from C$186
Aug
from C$202
Sep
from C$199
Oct
from C$202
Nov
from C$243
Dec
from C$202
Jan
from C$404
Feb
from C$442
Mar
from C$405

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 foundC$184
Cheapest month to flyJune
Average flight time1 hr, 48 mins
Most popular airlinePorter Airlines (Canada) Ltd
Average flights per week42

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

The best price we found for a round-trip flight from Toronto to Chicago Midway is C$184. 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 47 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.
There are 42 flights per week flying from Toronto to Chicago Midway, as of April 2025.
The cheapest month to fly from Toronto to Chicago Midway is usually April 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Toronto to Chicago Midway Airport on Saturday, June 7, 2025.
Yes – the average flight time is 1 hour and 47 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.
The cheapest airline that flies to Chicago Midway is Porter Airlines (Canada) Ltd.

How to find cheap flights to Chicago Midway from Toronto

Looking for cheap tickets from Toronto to Chicago Midway? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From Delta Air Lines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Toronto to Chicago Midway. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals to Chicago Midway from Toronto from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
  • Flex your dates to find the best Toronto–Chicago Midway ticket prices. If you're flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Chicago Midway from Toronto.
  • Set up a Price Alert. You can easily track the fare of your cheap Toronto–Chicago Midway flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Toronto and Chicago Midway? Make sure to tick "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business Class flights from Toronto and Chicago Midway. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago Midway, too. Check the difference in price as you search – you might just stumble on a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Toronto to Chicago Midway flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save the next time you travel.

    • Combine your flight to Chicago Midway from Toronto with hotels and car rental

    Once you've secured your cheap flight ticket from Toronto to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago Midway or nearby. You can also compare hundreds of car rental companies at once so you get the best car rental price for your trip.


More travel options

Cheap car rental at Frankfurt am Main AirportCheap car rental at Jeddah AirportManchester Airport car rentalCuracao Airport car rentalSnap Rentals car rentalBook hotels in JasperCheap flights from Cairo to VancouverCheap flights to Amarillo InternationalCheap round-trip tickets to Aruba
Round-trip tickets to Gimpo International AirportRound-trip flights from Toronto to LiberiaRound-trip tickets from Manchester to MilanCheap round-trip flights from Amritsar to Singapore ChangiRound-trip tickets from Palermo to VenicePan Pacific Airlines plane ticketsPlane tickets from Sydney to San Francisco InternationalVirgin America flightsCheap round-trip flights from New York John F. Kennedy to Toronto
Tickets to Bocas Del ToroCheap round-trip flights from Chicago to DubaiHelijet Airways flightsCheap flights from Dubai to WinnipegPlane tickets from Minsk International 2 to IstanbulFlights to Cape Verde

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.