Cheap flights from Toronto Island to Chicago Midway

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Flight deals from Toronto Island to Chicago Midway

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

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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.

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 foundC$310
Cheapest month to flyJune
Average flight time1 hr, 50 mins
Most popular airlinePorter Airlines (Canada) Ltd
Average flights per week35

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

The best price we found for a round-trip flight from Toronto Island to Chicago Midway is C$310. 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 (Canada) Ltd, Porter Airlines Inc and flyGTA Airlines fly direct from Toronto Island to Chicago Midway.
There are 35 flights per week flying from Toronto Island to Chicago Midway, as of April 2024.
The cheapest month to fly from Toronto Island to Chicago Midway is usually June.
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 Monday, June 24, 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.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago Midway is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Porter Airlines (Canada) Ltd offers the cheapest flight tickets to Chicago Midway.

Airlines That Fly from Toronto Island to Chicago Midway

Porter Airlines is the only airline offering flights from Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW). Skyscanner can help you find cheap flights from Toronto Island to Chicago Midway. Simply enter your travel date into the flight search, and we'll find you the lowest available fares. Want to compare air ticket prices over a range of dates? Try our Whole Month search option.

Departing from Billy Bishop Toronto City Airport

Billy Bishop Toronto City Airport's main terminal building is located on Toronto Island. Access to the main terminal is provided by a free ferry, a free shuttle service, and a pedestrian tunnel. The free shuttle and ferry services depart from the mainland approximately every 15 minutes from 5:15 a.m. until midnight. There are two TTC routes with stops near the ferry terminal on the mainland: 511 Bathurst and 509 Harbourfront.

Within the airport's main terminal, you'll find a few snack bars, retail shops, a duty-free outlet, and an espresso bar. There are also two lounges operated by Porter Airlines, where departing passengers can relax, read the newspaper, and enjoy complimentary drinks and snacks before taking off.

Arriving at Chicago Midway International Airport

Chicago Midway International Airport consists of one terminal building which is split into three concourse areas: Concourse A, Concourse B, and Concourse C. International arrivals are handled in Concourse A. Within the terminal's three concourse areas, you'll find a variety of retail shops, restaurants, snack bars, and souvenir kiosks, and coffee stands. Several ATMs and cash exchange desks are dotted throughout the airport.

Chicago Midway Airport is served by a Chicago Transit Authority (CTA) train that runs to downtown Chicago in around 30 minutes. There is also an Airport Express shuttle bus that departs every 15 minutes from the front of the main terminal building and runs to central Chicago. Other ground transportation options at Midway Airport are taxis, ride-share vans, and car rentals.

Practical Information

It is recommended that travellers on flights to the U.S. arrive at Billy Bishop Toronto City airport at least 60 minutes before their flight's scheduled departure time. In addition to ticket counter check-in at the airport, Porter airlines offers automatic check-in, self-service check-in kiosks, and a web check-in service that opens as early as 24 hours prior to departure.

What to Expect in Chicago: Travel Tips

The best times to visit Chicago are during the spring, summer, and fall months. January is the coldest month, with temperatures frequently falling below the freezing point. If you plan to drive in Chicago, keep in mind that gas, parking, and rental car fees are expensive. A more economical way to get around is by Chicago's extensive public transportation system, which is comprised of a network of reliable buses and a light-rail system known locally as the "L." Bus rides cost just $2.00 for adults, and there are even a few routes that serve the surrounding suburbs. Need an affordable place to stay in the city? Click here to search Skyscanner's deals on Chicago hotels.


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