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YTO - MDW

$129 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 6/24. 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 6/15
Sat 6/22

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 42,211,976 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Toronto to Midway (YTO-MDW)

 
These are the cheapest deals for flights from Toronto to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Toronto to Midway.

Recent one-way flight deals from Toronto to Midway

Only flying one-way? Below are some of the best one-way flight deals from Toronto to Midway found on KAYAK recently.

Recent last minute flight deals from Toronto to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Toronto to Midway.

Recent direct flight deals from Toronto to Midway

The latest deals for direct flights from Toronto to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Toronto to Midway

Find recent round-trip train or bus tickets from Toronto to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$217Porter Airlines
Find Deal
Tue, Jun 18 - Mon, Jun 24
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
$221Porter Airlines
Find Deal
Thu, Jun 13 - Sat, Jun 15
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$222Porter Airlines
Find Deal
Wed, Jun 26 - Wed, Jul 31
12:30 pm - 5:04 pmYYZ-MDW
5h 34m1 stop
9:24 am - 5:08 pmMDW-YYZ
6h 44m1 stop
$272Delta
Find Deal
Tue, Jul 16 - Sat, Jul 20
12:30 pm - 6:38 pmYYZ-MDW
7h 08m1 stop
5:45 pm - 10:53 pmMDW-YYZ
4h 08m1 stop
$273Delta
Find Deal
Tue, Jul 9 - Tue, Jul 16
9:45 am - 5:04 pmYYZ-MDW
8h 19m1 stop
9:34 am - 5:08 pmMDW-YYZ
6h 34m1 stop
$305KLM
Find Deal
Mon, Jun 17 - Wed, Jun 19
6:34 am - 6:07 pmYYZ-MDW
12h 33m1 stop
6:00 am - 9:57 pmMDW-YYZ
14h 57m1 stop
$316WestJet
Find Deal
Wed, May 29 - Wed, Jun 5
11:37 am - 9:46 pmYYZ-MDW
11h 09m1 stop
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
$317WestJet
Find Deal
Wed, Jun 12 - Wed, Jun 19
2:25 pm - 8:08 pmYTZ-MDW
6h 43m1 stop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$363
Find Deal
Fri, Sep 6 - Mon, Sep 9
10:45 am - 11:32 amYTZ-MDW
1h 47mnonstop
9:07 pm - 1:55 pmMDW-YTZ
15h 48m2 stops
$392
Find Deal
Sat, Jul 6 - Mon, Jul 8
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
$129Porter Airlines
Find Deal
Mon, Jun 24
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
$133Porter Airlines
Find Deal
Mon, Jul 1
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
$135Porter Airlines
Find Deal
Wed, Jun 12
7:50 am - 6:54 amYYZ-MDW
24h 04m1 stop
$151
Find Deal
Tue, May 21
6:15 am - 12:31 pmYYZ-MDW
7h 16m1 stop
$161Delta
Find Deal
Mon, Aug 5
12:30 pm - 5:04 pmYYZ-MDW
5h 34m1 stop
$163Delta
Find Deal
Wed, Jun 12
7:50 am - 6:54 amYYZ-MDW
24h 04m1 stop
$168
Find Deal
Tue, May 28
11:25 am - 5:59 pmYYZ-MDW
7h 34m1 stop
$176WestJet
Find Deal
Wed, Aug 21
12:30 pm - 6:05 pmYYZ-MDW
6h 35m1 stop
$178WestJet
Find Deal
Sat, Sep 28
6:04 am - 9:06 amYYZ-MDW
4h 02m1 stop
$197KLM
Find Deal
Wed, May 29
6:15 pm - 7:02 pmYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$388Porter Airlines
Find Deal
Sat, May 18 - Tue, May 28
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$404Porter Airlines
Find Deal
Sun, May 19 - Tue, May 28
6:15 pm - 7:02 pmYTZ-MDW
1h 47mnonstop
8:40 am - 11:22 amMDW-YTZ
1h 42mnonstop
$449Porter Airlines
Find Deal
Sat, May 18 - Sun, May 19
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
8:40 am - 11:22 amMDW-YTZ
1h 42mnonstop
$451Porter Airlines
Find Deal
Fri, May 17 - Sun, May 26
6:34 am - 11:02 amYYZ-MDW
5h 28m1 stop
9:46 am - 6:20 pmMDW-YYZ
7h 34m1 stop
$496WestJet
Find Deal
Sat, May 18 - Tue, May 28
7:10 pm - 6:07 pmYYZ-MDW
23h 57m1 stop
6:00 am - 12:10 pmMDW-YYZ
5h 10m1 stop
$522WestJet
Find Deal
Mon, May 20 - Fri, May 24
9:45 am - 5:06 pmYYZ-MDW
8h 21m1 stop
1:21 pm - 10:46 pmMDW-YYZ
8h 25m1 stop
$525Delta
Find Deal
Mon, May 20 - Fri, May 24
6:04 am - 12:40 pmYYZ-MDW
7h 36m1 stop
2:15 pm - 11:14 pmMDW-YYZ
7h 59m1 stop
$559Delta
Find Deal
Mon, May 20 - Fri, May 24
6:15 pm - 7:02 pmYTZ-MDW
1h 47mnonstop
9:08 pm - 5:36 pmMDW-YTZ
19h 28m2 stops
$693
Find Deal
Sat, May 18 - Sat, May 18
6:34 am - 11:02 amYYZ-MDW
5h 28m1 stop
10:33 pm - 4:49 pmMDW-YYZ
17h 16m2 stops
$1,326
Find Deal
Sat, May 18 - Sat, May 18
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$222Porter Airlines
Find Deal
Wed, Jun 26 - Wed, Jul 31
10:45 am - 11:32 amYTZ-MDW
1h 47mnonstop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$226Porter Airlines
Find Deal
Sat, Jul 13 - Wed, Jul 17
10:30 am - 11:17 amYTZ-MDW
1h 47mnonstop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$229Porter Airlines
Find Deal
Sun, Jul 14 - Wed, Jul 17
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$232Porter Airlines
Find Deal
Tue, Aug 13 - Thu, Aug 22
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$233Porter Airlines
Find Deal
Tue, Jun 11 - Fri, Jun 21
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
$235Porter Airlines
Find Deal
Wed, Jun 19 - Sat, Jun 22
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
$236Porter Airlines
Find Deal
Tue, Jun 11 - Sat, Jun 22
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
$237Porter Airlines
Find Deal
Wed, Jun 19 - Sat, Jun 22
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$238Porter Airlines
Find Deal
Wed, Jul 10 - Wed, Jul 17
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$240Porter Airlines
Find Deal
Tue, Jul 16 - Tue, Jul 23

Flights from Toronto to Midway - Travel Insights & Trends

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.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Toronto to Chicago Midway Airport.
Our data shows that the cheapest route for a one-way flight from Toronto to Chicago Midway Airport cost $124 and was between Toronto Island Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $182.

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

The average price of all flights from Toronto to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Toronto to Chicago Midway Airport, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway Airport back to Toronto, the best deals are generally found on Monday, with Thursday being the most expensive.

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 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 March, where tickets cost $216 on average. On the other hand, the most expensive months are June and August, where the average cost of tickets is $380 and $340 respectively.

How far in advance should I book a flight from Toronto 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 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 to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 16 days before departure.

Which airlines provide the cheapest flights from Toronto to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago Midway Airport from Toronto were found on Porter Airlines ($129) and Delta ($161), and the lowest round-trip tickets were found on Porter Airlines ($217) and Delta ($272).

Which airlines fly non-stop between Toronto 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 to Chicago Midway Airport.
There is just one airline that flies from Toronto to Chicago Midway Airport direct and that is Porter Airlines. The best one-way deal found from Porter Airlines for the route is $206.

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

Each day, there are between 2 and 3 nonstop flights that take off from Toronto and land in Chicago Midway Airport, with an average flight time of 1h 47m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 20 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 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 to Chicago Midway Airport take?

The average nonstop flight takes 1h 47m, covering a distance of 443 miles.

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

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

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

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

Good to know

Low season

April

High season

July

Cheapest flight

$129
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 9% increase in price.
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 $129 for a one-way ticket and $217 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, American Airlines, and United Airlines 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 Boeing 737 MAX 8 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.

See more FAQs

Top tips for finding a cheap flight from Toronto to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $136 or less one-way and $232 or less round-trip.

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

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

Nonstop 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

Nonstop 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
See more direct flights

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.
7.4
Porter AirlinesOverall score based on 415 reviews
7.6Boarding
8.2Crew
6.6Entertainment
7.4Food
7.5Comfort
Airline reviews

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

10.0 ExcellentJustin, Apr 2024YVR - YYZ
Read more about Porter Airlines reviews

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

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

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?

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.
6/24Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$129
7/1Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$133
6/12Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$135
5/21Tue
1 stop
24h 04mYYZ-MDW
$151
8/5Mon
1 stopDelta
7h 16mYYZ-MDW
$161
6/12Wed
1 stopDelta
5h 34mYYZ-MDW
$163
5/28Tue
1 stop
24h 04mYYZ-MDW
$168
8/21Wed
1 stopWestJet
7h 34mYYZ-MDW
$176
9/28Sat
1 stopWestJet
6h 35mYYZ-MDW
$178
5/29Wed
1 stopKLM
4h 02mYYZ-MDW
$197

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Last minute flights from Toronto 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.
5/18Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
5/28Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$388
5/19Sun
nonstopPorter Airlines
1h 47mYTZ-MDW
5/28Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$404
5/18Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
5/19Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$449
5/17Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
5/26Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$451
5/18Sat
multi-stopWestJet
5h 28mYYZ-MDW
5/28Tue
multi-stopWestJet
7h 34mMDW-YYZ
$496
5/20Mon
multi-stopWestJet
23h 57mYYZ-MDW
5/24Fri
multi-stopWestJet
5h 10mMDW-YYZ
$522
5/20Mon
multi-stopDelta
8h 21mYYZ-MDW
5/24Fri
multi-stopDelta
8h 25mMDW-YYZ
$525
5/20Mon
multi-stopDelta
7h 36mYYZ-MDW
5/24Fri
multi-stopDelta
7h 59mMDW-YYZ
$559
5/18Sat
nonstop
1h 47mYTZ-MDW
5/18Sat
multi-stop
19h 28mMDW-YTZ
$693
5/18Sat
multi-stop
5h 28mYYZ-MDW
5/18Sat
multi-stop
17h 16mMDW-YYZ
$1,326

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Toronto

Cabin classes:

$182

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