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YTO - MDW

C$ 181 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 23/5. 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
Fri 31/5
Fri 7/6

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, travellers have searched 43,740,974 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
5:15 p.m. - 7:57 p.m.MDW-YTZ
1h 42mdirect
C$ 314Porter Airlines
Find Deal
Tue, 28 May - Tue, 4 Jun
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 316Porter Airlines
Find Deal
Fri, 24 May - Mon, 27 May
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
5:15 p.m. - 7:57 p.m.MDW-YTZ
1h 42mdirect
C$ 317Porter Airlines
Find Deal
Thu, 23 May - Tue, 28 May
12:30 p.m. - 6:07 p.m.YYZ-MDW
6h 37m1 stop
5:00 p.m. - 11:14 p.m.MDW-YYZ
5h 14m1 stop
C$ 388Delta
Find Deal
Wed, 29 May - Sat, 1 Jun
12:30 p.m. - 5:06 p.m.YYZ-MDW
5h 36m1 stop
5:47 p.m. - 10:46 p.m.MDW-YYZ
3h 59m1 stop
C$ 390Delta
Find Deal
Thu, 23 May - Sun, 26 May
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
7:49 a.m. - 10:09 p.m.MDW-YTZ
13h 20m2 stops
C$ 416
Find Deal
Thu, 23 May - Wed, 29 May
12:30 p.m. - 6:07 p.m.YYZ-MDW
6h 37m1 stop
6:00 a.m. - 12:10 p.m.MDW-YYZ
5h 10m1 stop
C$ 436WestJet
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Tue, 28 May - Tue, 4 Jun
7:00 p.m. - 9:51 a.m.YYZ-MDW
15h 51m2 stops
12:45 p.m. - 9:59 p.m.MDW-YYZ
8h 14m1 stop
C$ 439WestJet
Find Deal
Fri, 14 Jun - Tue, 18 Jun
10:10 a.m. - 5:13 p.m.YTZ-MDW
8h 03m1 stop
12:30 p.m. - 3:12 p.m.MDW-YTZ
1h 42mdirect
C$ 457
Find Deal
Wed, 15 May - Sat, 25 May
6:04 a.m. - 12:40 p.m.YYZ-MDW
7h 36m1 stop
2:15 p.m. - 11:14 p.m.MDW-YYZ
7h 59m1 stop
C$ 634KLM
Find Deal
Wed, 15 May - Mon, 20 May

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 C$ 173 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 C$ 280.

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.
If you are looking for a flight deal from Toronto to Chicago Midway Airport, look for departures on Wednesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Monday is the cheapest day to fly and Thursday is 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 C$ 303 on average. On the other hand, the most expensive months are January and June, where the average cost of tickets is C$ 525 and C$ 517 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 62 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 last 3 days, Porter Airlines offered the best one-way deal for that route, at C$ 181. KAYAK users also found Toronto to Chicago Midway Airport round-trip flights on Porter Airlines from C$ 314 and on Delta from C$ 388.

Which airlines fly direct 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 C$ 266.

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 9:00 a.m. and most flights take off in the morning. Each week, there are 20 flights. The most frequent day of departure is Sunday, 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 is only one cabin class option available for the route, which is 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?

Direct flights from Toronto generally make it to Chicago Midway Airport in 1h 47m. The flying distance between the two cities is 1,148 km.

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

October

High season

July

Cheapest flight

C$ 181
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly (4% more expensive 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 C$ 132 for a one-way ticket and C$ 229 for a round-trip.

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

    Toronto is served by 2 major airports and there is only 1 main airport in Chicago Midway Airport. You will leave Toronto from one of these airports: Toronto Island or Toronto Pearson Intl. You will be arriving 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 direct 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 travellers 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 C$ 178 or less one-way and C$ 313 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 nonstop 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 nonstop flights
See more nonstop 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 435 reviews
7.4Food
7.6Boarding
8.2Crew
7.5Comfort
6.6Entertainment
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.

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?

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.
23/5Thu
directPorter Airlines
1h 47mYTZ-MDW
C$ 181
1/6Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 187
28/5Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 188
22/6Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 191
7/5Tue
1 stop
16h 16mYYZ-MDW
C$ 229
9/6Sun
1 stopDelta
3h 44mYYZ-MDW
C$ 230
13/6Thu
1 stopDelta
8h 19mYYZ-MDW
C$ 233
7/5Tue
2 stops
18h 46mYYZ-MDW
C$ 236
28/5Tue
1 stopWestJet
6h 37mYYZ-MDW
C$ 247
1/6Sat
1 stopWestJet
5h 25mYYZ-MDW
C$ 254

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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.
5/5Sun
directPorter Airlines
1h 47mYTZ-MDW
15/5Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 486
5/5Sun
directPorter Airlines
1h 47mYTZ-MDW
1/10Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 497
5/5Sun
directPorter Airlines
1h 47mYTZ-MDW
10/5Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 520
6/5Mon
directPorter Airlines
1h 47mYTZ-MDW
13/5Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 534
5/5Sun
multi-stopWestJet
5h 46mYYZ-MDW
15/5Wed
multi-stopWestJet
8h 15mMDW-YYZ
C$ 579
6/5Mon
multi-stopWestJet
20h 42mYYZ-MDW
13/5Mon
multi-stopWestJet
7h 04mMDW-YYZ
C$ 593
5/5Sun
multi-stopDelta
3h 34mYYZ-MDW
10/5Fri
multi-stopDelta
8h 25mMDW-YYZ
C$ 634
2/5Thu
multi-stopDelta
4h 51mYYZ-MDW
7/5Tue
multi-stopDelta
4h 10mMDW-YYZ
C$ 676
5/5Sun
direct
1h 47mYTZ-MDW
7/5Tue
multi-stop
18h 55mMDW-YTZ
C$ 1,017
4/5Sat
direct
1h 47mYTZ-MDW
9/5Thu
multi-stop
23h 34mMDW-YTZ
C$ 1,141

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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:

C$ 545
C$ 280

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