YTZ - MDW

C$ 113 Find Cheap Flights from Toronto Island to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto Island to Midway departing on 26/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Toronto Island to Midway (YTZ-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto Island to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto Island to Midway

jue., 11 sep. - jue., 18 sep.
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 161Porter Airlines
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lun., 1 sep. - lun., 8 sep.
Porter Airlines Logo
9:00 a.m. - 9:50 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 164Porter Airlines
Find Deal
mar., 26 ago. - mié., 3 sep.
Porter Airlines Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 165Porter Airlines
Find Deal
jue., 4 sep. - dom., 7 sep.
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 166Porter Airlines
Find Deal
jue., 28 ago. - dom., 31 ago.
Porter Airlines Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
10:40 a.m. - 1:20 p.m.MDW-YTZ
1h 40mdirect
C$ 168Porter Airlines
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mié., 27 ago. - mar., 2 sep.
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 171Porter Airlines
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vie., 5 sep. - dom., 7 sep.
Air Transat Logo
7:30 a.m. - 8:19 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
9:15 a.m. - 11:57 a.m.MDW-YTZ
1h 42mdirect
C$ 204Air Transat
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lun., 1 sep. - mié., 3 sep.
Air Transat Logo
9:00 a.m. - 9:50 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 228Air Transat
Find Deal
vie., 5 sep. - dom., 7 sep.
Air Transat Logo
7:30 a.m. - 8:19 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 230Air Transat
Find Deal
jue., 25 sep. - lun., 29 sep.
Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 270
Find Deal
Booking Insights

KAYAK's insights & trends for Toronto Island to Midway flights

Get data-powered insights and trends into flights from Toronto Island to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Toronto Island to Chicago Midway Airport?

The average price of all round-trip flights from Toronto Island Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

When flying from Toronto Island to Chicago Midway Airport, you should consider leaving on a Tuesday and avoid Mondays if you are looking for the best rates. For your return to Toronto Island, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Toronto Island Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Island Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Island Airport to Chicago Midway Airport is March, where tickets cost C$ 261 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is C$ 420 and C$ 406 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flightC$ 113
Best time to beat the crowds (15% less expensive on average)
Most popular time to fly and prices are also 9% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights from Toronto Island to Midway

Are your dates flexible? Find out the best times to travel from Toronto Island to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Toronto Island to Chicago Midway Airport flights

  • What is the cheapest flight from Toronto Island Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Toronto Island Airport to Chicago Midway Airport was C$ 82 for a one-way ticket and C$ 117 for a round-trip.

  • Which airports will I be using when flying from Toronto Island to Chicago Midway Airport?

    When flying out of Toronto Island you will be using Toronto Island. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Toronto Island to Chicago Midway Airport?

    All the following airlines offer inflight Wi-Fi service on the Toronto Island to Chicago Midway Airport flight route: Air Canada, United Airlines, American Airlines, WestJet, WestJet Encore, and Delta.

  • Which aircraft models fly most regularly from Toronto Island to Chicago Midway Airport?

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Toronto Island to Chicago Midway Airport flight route.

  • On which days can I fly direct from Toronto Island to Chicago Midway Airport?

    There are direct flights from Toronto Island to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Toronto Island to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto Island to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto Island to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Toronto Island is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto Island to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Toronto Island with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Island to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Toronto Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Toronto Island Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 128 or less one-way and C$ 199 or less round-trip.

Prefer to fly direct from Toronto Island to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto Island to Chicago Midway.
Find which airlines fly direct from Toronto Island Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Toronto Island to Chicago Midway

Monday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Tuesday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Wednesday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Thursday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Friday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Saturday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Sunday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

See more nonstop flights

Direct returns

Chicago Midway to Toronto Island

Monday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Tuesday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Wednesday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Thursday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Friday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Saturday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

Sunday

Air Transat,Porter Airlines

Air Transat,Porter Airlines

See more nonstop flights

Reviews of the top airline flying from Toronto Island to Midway

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto Island to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 318 reviews
8.7Crew
7.0Entertainment
8.2Boarding
7.6Food
8.0Comfort
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

Everything you need to know for your flight from Toronto Island to Midway

Information on your arrival and departure airports

Toronto Island (YTZ)
Midway (MDW)

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