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YTZ - MDW

Find cheap flights from Toronto Island to Chicago Midway Airport from $123

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 5/27. 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
0 bags
Sat 5/18
Sat 5/25

Search 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
In the last 7 days travelers have searched 44,471,296 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
$190Porter Airlines
Find Deal
Wed, Jun 5 - Mon, Jun 10
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$198Porter Airlines
Find Deal
Fri, May 10 - Mon, May 13
10:45 am - 11:32 amYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$199Porter Airlines
Find Deal
Sat, May 11 - Tue, May 14
6:15 pm - 7:02 pmYTZ-MDW
1h 47mnonstop
8:40 am - 11:22 amMDW-YTZ
1h 42mnonstop
$200Porter Airlines
Find Deal
Sat, May 11 - Sun, May 12
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$202Porter Airlines
Find Deal
Wed, May 8 - Wed, May 15
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
$203Porter Airlines
Find Deal
Wed, May 15 - Wed, May 22
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$204Porter Airlines
Find Deal
Wed, May 15 - Wed, May 22
6:15 pm - 7:02 pmYTZ-MDW
1h 47mnonstop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$205Porter Airlines
Find Deal
Sat, May 11 - Tue, May 14
2:25 pm - 8:08 pmYTZ-MDW
6h 43m1 stop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$284
Find Deal
Wed, Jun 5 - Mon, Jun 10
2:25 pm - 8:15 pmYTZ-MDW
6h 50m1 stop
8:40 am - 11:22 amMDW-YTZ
1h 42mnonstop
$298
Find Deal
Wed, May 22 - Sun, May 26

Flights from Toronto Island to Midway - Travel Insights & Trends

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 flights from Toronto Island Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Toronto Island to Chicago Midway Airport, look for departures on Mondays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Sunday is the cheapest day to fly and Friday is the most expensive.

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 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 $221 on average. On the other hand, the most expensive months are January and June, where the average cost of tickets is $383 and $377 respectively.

How far in advance should I book a flight from Toronto Island Airport to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Toronto Island Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Toronto Island Airport to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 62 days before departure.

Which airlines fly non-stop between Toronto Island Airport and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Toronto Island Airport to Chicago Midway Airport.
There is just one airline that flies from Toronto Island Airport to Chicago Midway Airport direct and that is Porter Airlines. The best one-way deal found from Porter Airlines for the route is $205.

How many flights are there between Toronto Island Airport and Chicago Midway Airport per day?

Each day, there are between 2 and 4 nonstop flights that take off from Toronto Island Airport and land in Chicago Midway Airport, with an average flight time of 1h 47m. The most common departure time is 8:00 pm and most flights take off in the evening. Each week, there are 26 flights. The most frequent day of departure is Wednesday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Toronto Island Airport and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 2 cabin class options for the route. These are Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Toronto Island to Chicago Midway Airport take?

The duration of a nonstop flight to Chicago Midway Airport from Toronto Island is typically 1h 47m. The journey crosses a distance of 442 miles.

What’s the earliest departure time from Toronto Island to Chicago Midway Airport?

Early birds can take the earliest flight from Toronto Island Airport at 9:20 am and will be landing in Chicago Midway Airport at 10:07 am.

What’s the latest departure time from Toronto Island to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Toronto Island Airport to Chicago Midway Airport jets off at 8:50 pm and lands at 9:37 pm.

Good to know

Low season

November

High season

August

Cheapest flight

$123
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 19% increase in price.
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 $123 for a one-way ticket and $190 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Toronto Island and on arrival in Chicago Midway Airport.

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

    Toronto Island and Chicago Midway Airport are both served by 1 main airport. You will leave Toronto Island from Toronto Island and will be arriving at Chicago Midway.

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

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

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

    The Boeing 737 MAX 8 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 nonstop 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 travelers 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. Booking your flights between Toronto Island and MDW can sometimes prove cheaper using this method.

  • 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.

See more FAQs

Top tips for finding a cheap flight from YTZ to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $133 or less one-way and $209 or less round-trip.

Prefer to fly non-stop from Toronto Island to Chicago Midway Airport?

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

Nonstop departures

Toronto Island 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

Nonstop returns

Chicago Midway to Toronto Island

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
See more direct flights

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.
7.4
Porter AirlinesOverall score based on 439 reviews
7.5comfort
6.6entertainment
8.2crew
7.4food
7.6boarding
Airline reviews

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

10.0 ExcellentJohn, Apr 2024YHZ - YUL
Read more about Porter Airlines reviews

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
5/27Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$123
5/13Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$132
6/24Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$133
5/16Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
$135
5/2Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
$140
5/9Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
$141
5/7Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$142
5/7Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$143
5/13Mon
1 stop
8h 03mYTZ-MDW
$187
6/24Mon
1 stop
10h 58mYTZ-MDW
$210

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Last minute flights from Toronto Island to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
4/21Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
5/2Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$357
4/22Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
4/25Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$371
4/20Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
4/30Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$386
4/21Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
4/28Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$397
4/23Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
4/24Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$402
4/22Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
4/24Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$409
4/22Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
4/25Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$411
4/23Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
4/30Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$414
4/21Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
4/25Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$417
4/23Tue
nonstop
1h 47mYTZ-MDW
4/24Wed
multi-stop
11h 00mMDW-YTZ
$508

Search by stops

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Toronto Island - Chicago Midway Airport Flights

Departure:

Toronto Island (YTZ)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Toronto Island

Cabin classes:

$149

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