Cheap flights from Toronto to Chicago Midway Airport

YTO — MDW
3 Oct — 10 Oct1
Return
1 adult
Economy
From?
To?
Mon 3/10
Mon 10/10

How to find the cheapest flight from Toronto (YTO) to Midway (MDW)

All the information you need to plan the best YTO to MDW flight in 2022: compare Toronto to Midway flight prices with the expected peak season, weather and rainfall in Midway.

YTO - MDW

Price

C$ 220 - C$ 379

MDW

Temperature

-5 - 23 °C

MDW

Rainfall

43 - 125 mm

Popular inFebruaryHigh demand for flights, 25% potential price rise
Cheapest inJuneBest time to find cheap flights, 23% potential price drop
Round-trip fromC$ 302From Toronto (YTO) to Chicago Midway
One-way fromC$ 181One-way flight from Toronto (YTO) to Chicago Midway

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 44 days in advance, which can save you up to 47% on flights from Toronto to Chicago Midway Airport compared to booking the week you need them. Waiting 44 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 424. For sooner than that we have options available in the next 3 days from C$ 526.

What is the cheapest month to fly from Toronto to Chicago Midway Airport?

June can be a great time to fly to Chicago Midway Airport from Toronto with a flight ticket averaging about C$ 382. Cheapflights users have found deals in the month of June for as cheap as C$ 222. The most expensive prices can be found in the month of October.

When is the cheapest time to fly from Toronto to Chicago Midway Airport (YTO - MDW)?

When flying from Toronto to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Toronto to Midway in September, October 2022

The best prices found for YTO to MDW flights for September, October
13 Oct. - 17 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 234

Porter Airlines

Pick Dates

Deal found 9/27/22

15 Oct. - 18 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 236

Porter Airlines

Pick Dates

Deal found 9/27/22

28 Oct. - 8 Nov.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 237

Porter Airlines

Pick Dates

Deal found 9/25/22

Toronto to Midway 2022 flight deals

Cheap flights to Midway from Toronto found for this year
13 Oct. - 17 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 234

Porter Airlines

Pick Dates

Deal found 9/27/22

15 Oct. - 18 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 236

Porter Airlines

Pick Dates

Deal found 9/27/22

28 Oct. - 8 Nov.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 237

Porter Airlines

Pick Dates

Deal found 9/25/22

Cheap Porter Airlines flights from Toronto to Midway

19 Nov. - 27 Nov.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 233

Porter Airlines

Pick Dates

Deal found 9/28/22

13 Oct. - 17 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 234

Porter Airlines

Pick Dates

Deal found 9/27/22

15 Oct. - 18 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 236

Porter Airlines

Pick Dates

Deal found 9/27/22

Cheap Delta flights from Toronto to Midway

15 Oct. - 18 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 28m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 45m
C$ 291

Delta

Pick Dates

Deal found 9/27/22

20 Oct. - 25 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 28m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 08m
C$ 292

Delta

Pick Dates

Deal found 9/25/22

27 Oct. - 3 Nov.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 36m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 08m
C$ 293

Delta

Pick Dates

Deal found 9/27/22

Direct flights to Midway from Toronto

Save time with Toronto to Midway direct flight deals
13 Oct. - 17 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 234

Porter Airlines

Pick Dates

Deal found 9/27/22

15 Oct. - 18 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 236

Porter Airlines

Pick Dates

Deal found 9/27/22

28 Oct. - 8 Nov.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 237

Porter Airlines

Pick Dates

Deal found 9/25/22

Last minute flights from Toronto to Midway

Late deals on round-trip flights to Midway from Toronto, departing today and this week
5 Oct. - 9 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 249

Porter Airlines

Pick Dates

Deal found 9/25/22

8 Oct. - 9 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 265

Porter Airlines

Pick Dates

Deal found 9/26/22

4 Oct. - 11 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 274

Porter Airlines

Pick Dates

Deal found 9/25/22

One-way flights to Midway from Toronto

The cheapest one-way flights from Toronto to Midway
19 Nov.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 144

Porter Airlines

Pick Dates

Deal found 9/27/22

21 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
C$ 145

Porter Airlines

Pick Dates

Deal found 9/25/22

15 Oct.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
C$ 147

Porter Airlines

Pick Dates

Deal found 9/25/22

Related info for your journey

Useful info, stats and facts about Toronto to Midway flights.

Which airlines flying from Toronto to Chicago Midway have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like Porter Airlines, WestJet, and Endeavor Airlines flying from Toronto to Chicago Midway have implemented new flexible cancellation policies.

Can I find flights from Toronto to Chicago Midway Airport for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago Midway Airport for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 233, but on average you can expect to pay C$ 255.

Are there direct flights from Toronto to Chicago Midway Airport for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago Midway Airport under C$ 300. A good price for a direct flight from Toronto to Chicago Midway Airport is less than C$ 258.

Are there last-minute flights available from Toronto to Chicago Midway Airport for under C$ 300?

There are currently 20+ open flights from Toronto to Chicago Midway Airport within the next 7 days for less than C$ 300.

What are the cheapest airlines flying from Toronto to Chicago Midway Airport round-trip?

Porter Airlines, at C$ 233, was found to be the cheapest airline from Toronto to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. Users have found that Porter Airlines is 40% cheaper than the other options available to this destination.

What are the most popular airlines that fly from Toronto to Chicago Midway Airport?

Before booking your flight from Toronto to Chicago Midway Airport check out the most popular airlines for this route: Endeavor Airlines, Delta or Porter Airlines.

What are the cheapest flights from Toronto to Chicago Midway Airport?

Looking at all options, your cheapest flight can be booked for C$ 331. While the most popular route (Toronto Pearson Intl - Chicago Midway) can be booked for C$ 292 on average our data indicates C$ 331 when flying from Toronto to Chicago Midway Airport.

Alternative routes for Toronto to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Ottawa to O'Hare Intlfrom C$ 330 pp

Top 3 airlines flying from Toronto to Midway

The chart below displays the airlines Cheapflights users travelling from Toronto to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Porter AirlinesCheapestC$ 254AverageC$ 345FlexibilityNo cancel feeOn-time52%COVID-19 safety
Search Porter Airlines flights
WestJetCheapestC$ 288AverageC$ 526FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
Endeavor AirlinesCheapestC$ 575AverageC$ 708FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Endeavor Airlines flights

Hourly flight availability from Toronto to Midway

See what time of day planes typically take off from Toronto to Midway
1%of flight departuresEarly morningMidnight to 6 am
42%of flight departuresMorning6 am to noon
57%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Toronto to Midway

See how many times per day planes take to the skies headed from Toronto to Midway
Sunday1daily flight
Monday3daily flights
Tuesday3daily flights
Wednesday3daily flights
Thursday3daily flights
Friday3daily flights
Saturday0daily flights