Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

YTZ - MDW

$133 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 2/13. 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
0 bags

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 41,299,237 times on KAYAK, and here is why:

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap Flight Deals from Toronto Island to Chicago Midway Airport (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 Chicago Midway Airport 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.

Recent round-trip flight deals from Toronto Island to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Toronto Island to Midway.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$232Porter Airlines
Find Deal
Fri, Feb 14 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$233Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$234Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$236Porter Airlines
Find Deal
Fri, Feb 14 - Mon, Feb 17
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$243Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$245Porter Airlines
Find Deal
Sat, Jan 25 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$268Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$269Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$325Air Transat
Find Deal
Sun, Jan 19 - Fri, Jan 24
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
6:22 pm - 3:40 pmMDW-YTZ
20h 18m2 stops
$405
Find Deal
Fri, Feb 21 - Sun, Feb 23

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 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 Wednesday and avoid Sundays 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 Wednesdays.

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 $219 (return) on average. On the other hand, the most expensive months are February and June, where the average cost of round-trip tickets is $303 and $303 respectively.

Can I save money by flying with a layover from Toronto Island Airport 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.
No, with an average price for the route of $251, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.
To get a below average price on the flight from Toronto Island Airport to Chicago Midway Airport, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low season

January

High season

June

Cheapest flight

$133
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 7% 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 $133 for a one-way ticket and $232 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, 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 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?

    You can catch a nonstop flight from Toronto Island to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday, and Sunday.

  • 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

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 $145 or less one-way and $236 or less round-trip.

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

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 direct 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 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.
7.9
Porter AirlinesOverall score based on 282 reviews
6.9Entertainment
8.7Crew
7.6Food
8.1Boarding
8.0Comfort
Airline reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

10.0 ExcellentJoan, Nov 2024YOW - YYZ
Read more Porter Airlines reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

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.
2/13Thu
nonstopPorter Airlines
1h 50mYTZ-MDW
$133
2/15Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
$134
1/24Fri
nonstopPorter Airlines
1h 50mYTZ-MDW
$145
1/26Sun
nonstopPorter Airlines
1h 50mYTZ-MDW
$148
1/24Fri
nonstopPorter Airlines
1h 50mYTZ-MDW
$150
1/25Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
$151
1/22Wed
nonstopPorter Airlines
1h 50mYTZ-MDW
$153
3/29Sat
nonstopAir Transat
1h 50mYTZ-MDW
$208
1/3Fri
nonstopAir Transat
1h 50mYTZ-MDW
$245
1/4Sat
3 stops
23h 53mYTZ-MDW
$402

Search by stops

Search by airline

Search by price

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.
12/30Mon
nonstopPorter Airlines
1h 50mYTZ-MDW
1/6Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$364
12/28Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
2/7Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$370
12/27Fri
nonstopPorter Airlines
1h 50mYTZ-MDW
1/20Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$393
12/26Thu
nonstopPorter Airlines
1h 50mYTZ-MDW
1/19Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$401
12/26Thu
nonstopPorter Airlines
1h 50mYTZ-MDW
12/30Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$402
12/26Thu
nonstopPorter Airlines
1h 50mYTZ-MDW
1/1Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$414
12/28Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
1/4Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
$416
12/28Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
1/1Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$417
12/26Thu
nonstopAir Transat
1h 50mYTZ-MDW
12/28Sat
nonstopAir Transat
1h 42mMDW-YTZ
$531
12/26Thu
nonstop
1h 50mYTZ-MDW
12/27Fri
multi-stop
9h 58mMDW-YTZ
$560

Search by stops

Search by airline

Search by price

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

Information on your arrival and departure airports

Midway (MDW)
Toronto Island (YTZ)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.