Cheap flights from Canada to Chicago Midway Airport

YYZ — MDW
28 Nov — 5 Dec1
Return
1 adult
Economy
From?
To?
Mon 28/11
Mon 5/12

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

Travellers have found it’s best to book a flight 56 days in advance to save up to 45% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 56 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Canada to Chicago Midway Airport 1-2 weeks in advance for as low as C$ 395, or C$ 484 for flights within the next 24 hours.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, June can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Canada in June are about C$ 357 on average during June, but can be found for as low as C$ 217.

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

When flying from Canada 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 Canada to Midway in November, December 2022

The best prices found for Canada to MDW flights for November, December
15 Dec. - 20 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 221

Porter Airlines

Deal found 23/11

5 Dec. - 12 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 223

Porter Airlines

Deal found 21/11

6 Dec. - 6 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 225

Porter Airlines

Deal found 22/11

Canada to Midway 2022 flight deals

Cheap flights to Midway from Canada found for this year
15 Dec. - 20 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 221

Porter Airlines

Deal found 23/11

5 Dec. - 12 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 223

Porter Airlines

Deal found 21/11

6 Dec. - 6 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 225

Porter Airlines

Deal found 22/11

Cheap Delta flights from Canada to Midway

6 Dec. - 9 Dec.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 28m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m
C$ 283

Delta

Deal found 22/11

7 Dec. - 12 Dec.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

4h 01m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 50m
C$ 294

Delta

Deal found 20/11

8 Dec. - 10 Dec.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 58m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

4h 35m
C$ 298

Delta

Deal found 22/11

Cheap Porter Airlines flights from Canada to Midway

15 Dec. - 20 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 221

Porter Airlines

Deal found 23/11

25 Feb. - 10 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 223

Porter Airlines

Deal found 21/11

6 Dec. - 6 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 225

Porter Airlines

Deal found 22/11

Direct flights to Midway from Canada

Save time with Canada to Midway direct flight deals
15 Dec. - 20 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 221

Porter Airlines

Deal found 23/11

25 Feb. - 10 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 223

Porter Airlines

Deal found 21/11

14 Apr. - 16 Apr.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 224

Porter Airlines

Deal found 23/11

Last minute flights from Canada to Midway

Late deals on round-trip flights to Midway from Canada, departing today and this week
3 Dec. - 7 Dec.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

4h 01m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

7h 30m
C$ 312

Delta

Deal found 21/11

30 Nov. - 5 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 316

Porter Airlines

Deal found 21/11

2 Dec. - 5 Dec.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

4h 01m
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

3h 38m
C$ 318

Delta

Deal found 21/11

One-way flights to Midway from Canada

The cheapest one-way flights from Canada to Midway
23 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 135

Porter Airlines

Deal found 22/11

4 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 139

Porter Airlines

Deal found 22/11

6 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 141

Porter Airlines

Deal found 20/11

Related info for your journey

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

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

Porter Airlines, Delta, and WestJet are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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

Yes, there are multiple flights from Canada to Chicago Midway Airport for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 221, but on average you can expect to pay C$ 243.

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

Cheapflights has 20 direct flights from Canada to Chicago Midway Airport under C$ 300. A good price for a direct flight from Canada to Chicago Midway Airport is less than C$ 241.

Are there last-minute flights available from Canada to Chicago Midway Airport for under C$ 400?

There are currently 20+ open flights from Canada to Chicago Midway Airport within the next 7 days for less than C$ 400.

What are the most popular routes from Canada to Chicago Midway Airport?

While some choose either Toronto Island - Chicago Midway or Toronto Pearson Intl - Chicago Midway, Montreal Pierre Elliott Trudeau Intl - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.

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

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

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

The cheapest flight price from Canada to Chicago Midway Airport is C$ 261. On average you can expect to pay C$ 261. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago Midway), can usually be booked for C$ 277.

Departure points for flights from Canada to Midway

Select to see more specific information for flights to Midway from all departure points in Canada

Top 3 airlines flying from Canada to Midway

The chart below displays the airlines Cheapflights users travelling from Canada 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$ 225AverageC$ 360FlexibilityNo cancel feeOn-time52%COVID-19 safety
Search Porter Airlines flights
WestJetCheapestC$ 282AverageC$ 514FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
Endeavor AirlinesCheapestC$ 525AverageC$ 678FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Endeavor Airlines flights

Hourly flight availability from Canada to Midway

See what time of day planes typically take off from Canada to Midway
1%of flight departuresEarly morningMidnight to 6 am
31%of flight departuresMorning6 am to noon
68%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM