YTO - MDW

$105 Find Cheap Flights from Toronto 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 to Midway departing on 9/13. 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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Flight Deals

Cheap Flights from Toronto to Midway (YTO-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto 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 to Midway

Thu, Sep 18 - Mon, Sep 22
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$172Porter Airlines
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Fri, Sep 26 - Tue, Sep 30
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$173Porter Airlines
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Sun, Oct 5 - Mon, Oct 6
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$212Air Transat
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Tue, Oct 7 - Sun, Oct 12
Delta Logo
12:15 pm - 6:25 pmYYZ-MDW
7h 10m1 stop
Delta Logo
9:35 am - 2:45 pmMDW-YYZ
4h 10m1 stop
$212Delta
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Thu, Sep 18 - Sat, Sep 20
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$216Air Transat
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Thu, Oct 2 - Thu, Oct 9
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$222
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Tue, Sep 23 - Thu, Oct 2
Delta Logo
4:12 pm - 6:35 pmYYZ-MDW
3h 23m1 stop
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
$224Delta
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Thu, Sep 11 - Mon, Sep 15
Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$224
Find Deal
Tue, Sep 16 - Tue, Sep 23
WestJet Logo
7:45 am - 9:36 pmYYZ-MDW
14h 51m1 stop
WestJet Logo
9:20 am - 12:31 amMDW-YYZ
14h 11m2 stops
$265WestJet
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Wed, Oct 1 - Fri, Oct 3
WestJet Logo
1:20 pm - 9:36 pmYYZ-MDW
9h 16m1 stop
WestJet Logo
7:15 pm - 6:03 pmMDW-YYZ
21h 48m2 stops
$266WestJet
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Booking Insights

KAYAK's insights & trends for Toronto to Midway flights

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

How much is a round-trip flight from Toronto to Chicago Midway Airport?

What is the cheapest Toronto to Chicago Midway Airport flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Toronto to Chicago Midway Airport costs $120 on the route between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). It is also the most popular route.

What is the cheapest month to fly from Toronto 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 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 to Chicago Midway Airport is May, where tickets cost $206 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $322 and $277 respectively.

Can I save money by flying with a layover from Toronto to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $402 on average.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$105
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights from Toronto to Midway

Are your dates flexible? Find out the best times to travel from Toronto 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 to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Toronto to Chicago Midway Airport was $105 for a one-way ticket and $172 for a round-trip.

  • Do I need a passport to fly between Toronto and Chicago Midway Airport?

    Yes, you’ll need a passport to travel to Chicago Midway Airport from Toronto.

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

    On your way to Chicago Midway Airport, you’ll fly out from one of these Toronto airports: Toronto Island or Toronto Pearson Intl. You’ll be landing at Chicago Midway.

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

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

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

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

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

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

  • How does KAYAK find such low prices on flights from Toronto 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 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 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 is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto 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 with another airline.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $153 or less one-way and $182 or less round-trip.

Prefer to fly direct from Toronto 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 to Chicago Midway.
Find which airlines fly direct from Toronto to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Toronto to Chicago Midway

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more direct flights

Direct returns

Chicago Midway to Toronto

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more direct flights

Reviews of the top airline flying from Toronto 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 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 336 reviews
7.6Food
8.2Boarding
8.7Crew
8.0Comfort
7.0Entertainment
Airline reviews

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

8.0 ExcellentStephanie, Aug 2025YYZ - LGA
Read more Porter Airlines reviews

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

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.

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

Information on your arrival and departure airports

Midway (MDW)

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