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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.
Chicago.$289 per passenger.Departing Sat, 9 May, returning Fri, 15 May.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 9 May, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 15 May, arriving in Toronto Island.Price includes taxes and charges.From $289, select.
Chicago.$290 per passenger.Departing Mon, 27 Apr, returning Wed, 29 Apr.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon, 27 Apr, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Wed, 29 Apr, arriving in Toronto Island.Price includes taxes and charges.From $290, select.
Chicago.$294 per passenger.Departing Tue, 2 Jun, returning Fri, 5 Jun.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue, 2 Jun, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 5 Jun, arriving in Toronto Island.Price includes taxes and charges.From $294, select.
Chicago.$297 per passenger.Departing Mon, 30 Mar, returning Thu, 2 Apr.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon, 30 Mar, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Thu, 2 Apr, arriving in Toronto Island.Price includes taxes and charges.From $297, select.
Chicago.$342 per passenger.Departing Sun, 26 Apr, returning Sun, 3 May.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sun, 26 Apr, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sun, 3 May, arriving in Toronto Island.Price includes taxes and charges.From $342, select.
Chicago.$342 per passenger.Departing Thu, 28 May, returning Tue, 2 Jun.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 28 May, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 2 Jun, arriving in Toronto Island.Price includes taxes and charges.From $342, select.
Chicago.$342 per passenger.Departing Wed, 18 Mar, returning Wed, 25 Mar.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed, 18 Mar, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Wed, 25 Mar, arriving in Toronto Island.Price includes taxes and charges.From $342, select.
Chicago.$381 per passenger.Departing Wed, 2 Sep, returning Sun, 6 Sep.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed, 2 Sep, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sun, 6 Sep, arriving in Toronto Island.Price includes taxes and charges.From $381, select.

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 May.
Feb
from $878
Mar
from $342
Apr
from $290
May
from $289
Jun
from $294
Jul
from $465
Aug
from $494
Sep
from $381
Oct
from $494
Nov
from $534
Dec
from $531
Jan
Find prices

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.

Chicago Midway

14km from central Chicago
ClosestCheapest
from $289
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Chicago O'Hare International

25km from central Chicago
from $308
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Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
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Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight found$289
Cheapest month to flyMay
Average flight time1 hr, 50 mins
Most popular airlinePorter Airlines
Average flights per week86

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 $289. 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, Porter Airlines Inc and Air Transat fly direct from Toronto to Chicago Midway.
As of February 2026, there are 86 flights per week flying from Toronto to Chicago Midway.
The cheapest month to fly from Toronto to Chicago Midway is usually May.
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, 9 May 2026.
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.
The cheapest airline that flies to Chicago Midway is Porter Airlines .

Travelling from Toronto to Chicago Midway International Airport (MDW): What you need to know

  • When looking for your flight from Toronto to Chicago Midway International Airport (MDW), there's a good range of airports you can depart from. Pearson International Airport (YYZ), Billy Bishop Toronto City Airport (YTZ) and Region of Waterloo International Airport (YKF) are Toronto's major terminals.

  • Chicago is one hour behind Toronto. Chicago Midway International Airport is located in Chicago, which runs on the UTC-5 timezone.

  • Get to the airport on time so you don't miss your flight from Toronto to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.

  • If you're heading away during a bank holiday or other peak period, allow for even more time. Get there two hours ahead of domestic flights and up to four hours before international departures. Lines at check-in and security will be longer.

Airports in Toronto

Pearson International Airport (YYZ)

Billy Bishop Toronto City Airport (YTZ)

  • Consider starting your trip from Billy Bishop Toronto City Airport (YTZ). You can book a direct Toronto to Chicago Midway International Airport (MDW) flight ticket with departures from here.

  • From YTZ, direct flights from Toronto to MDW can be booked with Porter Airlines.

  • Porter Airlines has the largest share of bookings on the YTZ to MDW route.

  • With 69.15% of services landing on schedule, Porter Airlines is the top on-time carrier flying between Billy Bishop Toronto City Airport and Chicago Midway International Airport.

  • On public transport, you can travel from central Toronto to YTZ in about 40 minutes. The terminal is roughly 3 kilometres away, and making the journey by car will take approximately 35 minutes.

  • Start your holiday sooner with an extra night away from home. Before your Toronto to MDW flight, unwind in one of these hotels close to Billy Bishop Toronto City Airport:

  • When it comes to keeping flights punctual, Billy Bishop Toronto City Airport has an on-time arrival rate of 62.09%.

Region of Waterloo International Airport (YKF)

  • The journey time to YKF from the centre of Toronto is around 4 hours 5 minutes on public transport. If you're planning to travel by car, it'll take you roughly 1 hour 15 minutes to cover the 105 kilometres or so.

  • Stay in bed a little longer and still make your Toronto to Chicago Midway International Airport flight with plenty of time to spare. These hotels near Region of Waterloo International Airport make it a breeze to get to the terminal if you're flying out first thing:

  • Flights that leave from YKF land at their destination on schedule 63.64% of the time.

About Chicago Midway International Airport (MDW)

  • If you have a late flight from Toronto to Chicago Midway International Airport, nothing beats the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and resting soon after at one of these hotels near MDW:

  • Travel at your own speed with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and find adventure across Chicago and beyond.

  • To get the lowest price, reserve your ride around four weeks ahead of your Toronto to Chicago Midway International Airport flight.

  • MDW is located at 5700 South Cicero.

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

  • Chicago Midway International Airport is around 14 kilometres from central Chicago. How long it takes to get there by car hire or cab depends on the time of day. Do some research before your trip.

  • When travelling by public transport, expect a journey of around 45 minutes.

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

  • The cheapest price we've found for a one-way ticket from Toronto to Chicago Midway International Airport is $172. For a return flight on this route, the best price is $289. Depending on how early you book and the availability, these fares may change.

  • Booking in advance is often the key to scoring a cheap flight from Toronto to MDW. Flight prices rise as demand increases, so the closer your departure date, the more you'll likely spend on your ticket.

  • The 'Whole month' search tool will show you the cheapest Toronto to Chicago Midway International Airport tickets throughout the month. It's an easy way to snap up a bargain if your travel dates aren't set in stone.

  • You don't need to check every day to find out if fares have dropped when you set up a Price Alert. We'll let you know as soon as a new deal shows up on flight tickets from Toronto to MDW.

  • Filters make it easier to dig up a deal for your flight from Toronto to Chicago Midway International Airport. Pick the departure times, airlines and number of stops that line up with your plans. Then sort the results by 'Cheapest' to bring up the lowest fares right away.

The best time to fly from Toronto to Chicago Midway International Airport (MDW)

  • It's time to decide your travel dates for your flight from Toronto to Chicago Midway International Airport (MDW). July is when most people visit Chicago. If you like things a bit more low-key, think about going in May.

  • Before locking in your Toronto to MDW flight ticket, consider the kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • If you want cooler conditions, search for a cheap ticket from Toronto to Chicago Midway International Airport in January when temperatures are between -12ºC and 3ºC.

More about Chicago

Explore more of the United States

  • You've done Chicago, now it's time to discover other parts of the United States. Travel around 257 kilometres south-east to Indianapolis to tick off its top attractions. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, you'll have a packed itinerary ahead.

  • Milwaukee is another standout destination in the United States and is around 137 kilometres north of Chicago. No trip is complete without experiencing Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County 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.